Which roles would norepinephrine mechanism of action performed in managing anaphylaxis

Summary

Epinephrine is a hormone and neurotransmitter used to treat allergic reactions, to restore cardiac rhythm, and to control mucosal congestion, glaucoma, and asthma.

Inhaltsverzeichnis Show

Transporters
What is the mechanism of action of norepinephrine?
How does norepinephrine increase heart rate?
Which vasoconstrictor is usually associated with the treatment of anaphylaxis?
What receptors does epinephrine work?

Brand Names

Adrenalin, Allerject, Anapen, Articadent, Astracaine, Auvi-Q, Citanest, Citanest Forte, Emerade, Epipen, Lignospan, Marcaine, Marcaine With Epinephrine, Octocaine, Octocaine With Epinephrine, Orabloc, Scandonest, Sensorcaine, Sensorcaine With Epinephrine, Septanest, Septocaine, Symjepi, Ultacan, Ultracaine, Vivacaine, Xylocaine, Xylocaine With Epinephrine, Zorcaine

Generic NameEpinephrineDrugBank Accession NumberDB00668Background

Epinephrine, also known as adrenaline, is a hormone and neurotransmitter and produced by the adrenal glands that can also be used as a drug due to its various important functions. Though it has long been used in the treatment of hypersensitivity reactions, epinephrine in the auto-injector form (EpiPen) has been available since 1987 in the USA. Many new products/biosimilars and dosage routes have been approved under various names over the last several decades 10, 11, 12. On August 16, 2018, Teva Pharmaceuticals USA gained approval to market its generic epinephrine auto-injector in 0.3 mg and 0.15 mg strengths 8. Dosage delivery routes for epinephrine include intravenous, inhalation, nebulization, intramuscular injection, and subcutaneous injection.

In general, the most common uses of parenteral epinephrine are to relieve respiratory distress due to bronchospasm, to provide rapid relief of hypersensitivity (anaphylactic or anaphylactoid) reactions to drugs, animal serums and other allergens, and to prolong the action of infiltration anesthetics 20. In addition to the above functions, epinephrine is the primary drug administered during cardiopulmonary resuscitation (CPR) to reverse cardiac arrest 3, 4. It can be used in severe cases of croup 14.

TypeSmall MoleculeGroupsApproved, Vet approvedStructure

WeightAverage: 183.2044
Monoisotopic: 183.089543287 Chemical FormulaC9H13NO3Synonyms

(−)-(R)-epinephrine
(−)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcohol
(−)-adrenaline
(R)-(-)-Adnephrine
(R)-(-)-Adrenaline
(R)-(-)-Epinephrine
(R)-(-)-Epirenamine
(R)-(−)-adrenaline
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
Adrenaline
Adrénaline
Epinefrin
Epinefrina
Epinephrin
Epinephrine
Epinephrinum
L-Adrenaline
Levoepinephrine

External IDs

NSC-62786

Indication

Epinephrine injection is indicated in the emergency treatment of type I allergic reactions, including anaphylaxis. It is also used to increase mean arterial blood pressure in adult patients with hypotension associated with septic shock.17

Epinephrine's cardiac effects may be of use in restoring cardiac rhythm in cardiac arrest due to various causes but is not used in cardiac failure or in hemorrhagic, traumatic, or cardiogenic shock 18.

Epinephrine is used as a hemostatic agent. It is also used in treating mucosal congestion of hay fever, rhinitis, and acute sinusitis; to relieve bronchial asthmatic paroxysms; in syncope due to complete heart block or carotid sinus hypersensitivity; for symptomatic relief of serum sickness, urticaria, angioneurotic edema; for resuscitation in cardiac arrest following anesthetic accidents; in simple (open angle) glaucoma; for relaxation of uterine musculature and to inhibit uterine contractions. Epinephrine injection can be utilized to prolong the action of local anesthetics 18.

In addition to the above, epinephrine is used as an over the counter (OTC) agent for the intermittent symptoms of asthma, such as wheezing, tightness of chest and shortness of breath 19. It is also used for the maintenance of mydriasis during intraocular surgery 15.

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Associated Conditions

Anaphylaxis
Angioneurotic Edema
Bleeding
Bronchospasm
Complete Heart Block
Hypotension
Idiopathic Anaphylaxis
Laryngotracheobronchitis
Mild Intermittent Asthma
Nasal Congestion
Open Angle Glaucoma (OAG)
Respiratory Distress
Severe Asthma
Syncope
Type I Hypersensitivity
Urticaria
Uterine Contractions
Ventricular Fibrillation
Resuscitation in cardiac arrest following anesthetic accidents
Severe hypersensitivity
Unresponsive Asystole
Unresponsive Bradycardia

Contraindications & Blackbox Warnings

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Pharmacodynamics

Epinephrine is a sympathomimetic drug. It causes an adrenergic receptive mechanism on effector cells and mimics all actions of the sympathetic nervous system except those on the facial arteries and sweat glands 18.

Important effects of epinephrine include increased heart rate, myocardial contractility, and renin release via beta-1 receptors. Beta-2 effects produce bronchodilation which may be useful as an adjunct treatment of asthma exacerbations as well as vasodilation, tocolysis, and increased aqueous humor production 15. In croup, nebulized epinephrine is associated with both clinically and statistically significant transient reduction of croup symptoms 30 minutes post-treatment 7. Epinephrine also alleviates pruritus, urticaria, and angioedema and may be helpful in relieving gastrointestinal and genitourinary symptoms associated with anaphylaxis because of its relaxing effects on the smooth muscle of the stomach, intestine, uterus, and urinary bladder Label.

Mechanism of action

Epinephrine acts on alpha and beta-adrenergic receptors. Epinephrine acts on alpha and beta receptors and is the strongest alpha receptor activator 18. Through its action on alpha-adrenergic receptors, epinephrine minimizes the vasodilation and increased the vascular permeability that occurs during anaphylaxis, which can cause the loss of intravascular fluid volume as well as hypotension. Epinephrine relaxes the smooth muscle of the bronchi and iris and is a histamine antagonist, rendering it useful in treating the manifestations of allergic reactions and associated conditions 20. This drug also produces an increase in blood sugar and increases glycogenolysis in the liver 18. Through its action on beta-adrenergic receptors, epinephrine leads to bronchial smooth muscle relaxation that helps to relieve bronchospasm, wheezing, and dyspnea that may occur during anaphylaxis Label.

Target	Actions	Organism
AAlpha-1A adrenergic receptor	agonist	Humans
AAlpha-1B adrenergic receptor	agonist	Humans
ABeta-1 adrenergic receptor	agonist	Humans
ABeta-2 adrenergic receptor	agonist	Humans
AAlpha-2A adrenergic receptor	agonist	Humans
AAlpha-2B adrenergic receptor	agonist	Humans
UAlpha-1D adrenergic receptor	antagonist	Humans
UTumor necrosis factor	antagonist agonist	Humans

Absorption

Following I.V. (intravenous) injection, epinephrine disappears rapidly from the blood stream. Subcutaneously or I.M. (intramuscular) administered epinephrine has a rapid onset and short duration of action. Subcutaneous (SC) administration during asthmatic attacks may produce bronchodilation within 5 to 10 minutes, and maximal effects may occur within 20 minutes. The drug becomes fixed in the tissues rapidly 18, Label.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Epinephrine is rapidly inactivated mainly by enzymic transformation to metanephrine or normetanephrine, either of which is then conjugated and excreted in the urine in the form of both sulfates and glucuronides. Either sequence results in the formation of 3-methoxy-4- hydroxy-mandelic acid(vanillylmandelic acid, VMA) which is shown to be detectable in the urine 18. Epinephrine is rapidly inactivated in the body mostly by the enzymes COMT (catechol-O-methyltransferase) and MAO (monoamine oxidase). The liver is abundant in the above enzymes, and is a primary, although not essential, tissue in the degradation process 13.

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Route of elimination

The majority of the dose of epinephrine is seen excreted in the urine 13, Label. About 40% of a parenteral dose of epinephrine is excreted in urine as metanephrine, 40% as VMA, 7% as 3-methoxy-4-hydroxyphenoglycol, 2% as 3,4-dihydroxymandelic acid, and the rest as acetylated derivatives. These metabolites are excreted mainly as the sulfate conjugates and, to a lesser extent, the glucuronide conjugates. Only small amounts of the drug are excreted completely unchanged 16.

Half-life

The plasma half-life is approximately 2-3 minutes. However, when administered by subcutaneous or intramuscular injection, local vasoconstriction may delay absorption so that epinephrine's effects may last longer than the half-life suggests 13.

Clearance

Intravenous injection produces an immediate and intensified response. Following intravenous injection, epinephrine disappears rapidly from the blood stream 20.

Adverse Effects

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Toxicity

Skin, LD50 = 62 mg/kg (rat) MSDS

Pregnancy

Epinephrine is teratogenic in rats when given in doses about 25 times the human doses. It is unknown whether epinephrine can cause fetal harm when administered to a pregnant woman or can affect reproduction capacity. Epinephrine should be given to a pregnant woman only if clearly required in critical situations/emergencies 20.

Labor and Delivery Parenteral administration of epinephrine, if used as support for blood pressure during low or other spinal anesthesia for delivery, can lead to the acceleration of fetal heart rate and should not be used in obstetrics when maternal blood pressure is higher than 130/80. Epinephrine may delay the second stage of labour.

Common and generalized adverse effects: Transient and minor side effects of anxiety, headache, fear, and palpitations may occur with therapeutic doses of epinephrine, especially in hyperthyroid individuals. Repeated local injections may result in necrosis at sites of injection due to vascular constriction. Cerebral hemorrhage; hemiplegia; subarachnoid hemorrhage; anginal pain in patients with angina pectoris; anxiety; restlessness; throbbing headache; tremor; weakness; dizziness; pallor; respiratory difficulty; palpitation; apprehensiveness; sweating; nausea; vomiting Label.

Cardiovascular effects: Inadvertently induced high arterial blood pressure may result in angina pectoris (especially when coronary insufficiency is present), cardiac ischemia, or aortic rupture Label, 15. Epinephrine may cause serious cardiac arrhythmias in patients not suffering from heart disease and patients with organic heart disease receiving drugs that sensitize the cardiac muscle. With the injection of epinephrine 1:1,000, a paradoxical but transient lowering of blood pressure, bradycardia and apnea may occur immediately post-injection Label.

Cerebrovascular hemorrhage: Overdosage or accidental I.V. injection of epinephrine may lead to cerebrovascular hemorrhage resulting from the sharp rise in blood pressure Label.

Renal vasoconstriction: Parenterally administered epinephrine initially may produce constriction of renal blood vessels and decrease urine formation. High doses may cause complete renal shutdown 20.

Pulmonary edema: Fatality may also result from pulmonary edema due to the peripheral constriction and cardiac stimulation produced by epinephrine injection Label.

Digital vasoconstriction: Since epinephrine is a strong vasoconstrictor, accidental injection into the digits, hands or feet may lead to the loss of blood flow to the affected area. Treatment should be directed at vasodilation in addition to further treatment of anaphylaxis Label.

Pathways

Pathway	Category
Aromatic L-Aminoacid Decarboxylase Deficiency	Disease
Tyrosine Metabolism	Metabolic
Catecholamine Biosynthesis	Metabolic
Tyrosinemia Type I	Disease
Disulfiram Action Pathway	Drug action
Alkaptonuria	Disease
Hawkinsinuria	Disease
Tyrosinemia, Transient, of the Newborn	Disease
Tyrosine Hydroxylase Deficiency	Disease
Dopamine beta-Hydroxylase Deficiency	Disease
Monoamine Oxidase-A Deficiency (MAO-A)	Disease
Epinephrine Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Not AvailableDrug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Approved
Vet approved
Nutraceutical
Illicit
Withdrawn
Investigational
Experimental
All Drugs

Drug	Interaction
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Abaloparatide	The risk or severity of adverse effects can be increased when Epinephrine is combined with Abaloparatide.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Epinephrine.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Epinephrine.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Epinephrine.
Acarbose	The therapeutic efficacy of Acarbose can be decreased when used in combination with Epinephrine.
Acebutolol	The therapeutic efficacy of Acebutolol can be increased when used in combination with Epinephrine.
Aceclofenac	The risk or severity of hypertension can be increased when Epinephrine is combined with Aceclofenac.
Acemetacin	The risk or severity of hypertension can be increased when Epinephrine is combined with Acemetacin.
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Epinephrine.
Acetazolamide	The risk or severity of Cardiac Arrhythmia can be increased when Epinephrine is combined with Acetazolamide.

Food InteractionsNo interactions found.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Epinephrine acetate	M1NJX34RVJ	97289-42-4	CEBXQLPKMNOIHN-FVGYRXGTSA-N
Epinephrine bitartrate	30Q7KI53AK	51-42-3	YLXIPWWIOISBDD-NDAAPVSOSA-N
Epinephrine hydrochloride	WBB047OO38	55-31-2	ATADHKWKHYVBTJ-FVGYRXGTSA-N

International/Other BrandsEpi EZ Pen JRBrand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Adrenaclick	Injection	0.3 mg/0.3mL	Subcutaneous	Amedra Pharmaceuticals LLC	2009-11-25	2014-11-01
Adrenaclick	Injection	1 mg/1mL	Intramuscular; Subcutaneous	Sciele Pharma, Inc.	2009-12-15	2013-08-19
Adrenaclick	Injection	0.15 mg/0.15mL	Subcutaneous	Amedra Pharmaceuticals LLC	2009-11-25	2014-11-01
Adrenaclick	Injection	1 mg/1mL	Intramuscular; Subcutaneous	Sciele Pharma, Inc.	2009-12-15	2013-08-19
Adrenaclick 0.15mg Auto-injector	Solution	0.15 mg / 0.15 mL	Intramuscular	Amedra Pharmaceuticals LLC	Not applicable	Not applicable
Adrenaclick 0.30mg Auto-injector	Solution	0.30 mg / 0.30 mL	Intramuscular	Amedra Pharmaceuticals LLC	Not applicable	Not applicable
Adrenalin	Injection	1 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Par Pharmaceutical, Inc.	2013-07-01	Not applicable
Adrenalin	Injection	1 mg/1mL	Intracardiac; Intramuscular; Intraspinal; Intravenous; Subcutaneous	JHP Pharmaceuticals, LLC.	2007-10-01	2013-07-31
Adrenalin	Solution	1 mg / mL	Intramuscular; Intravenous; Subcutaneous	Erfa Canada 2012 Inc	1951-12-31	Not applicable
Adrenalin	Injection	1 mg/1mL	Intramuscular; Intraocular; Subcutaneous	Remedy Repack	2015-03-24	2017-03-20

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Epinephrine	Injection	0.3 mg/0.3mL	Intramuscular	Mylan Specialty L.P.	2016-12-15	Not applicable
Epinephrine	Injection	0.15 mg/0.15mL	Subcutaneous	Sina Health Inc	2010-04-01	Not applicable
Epinephrine	Injection	0.3 mg/0.3mL	Subcutaneous	Medical Purchasing Solutions, Llc	2010-04-01	Not applicable
Epinephrine	Injection	0.15 mg/0.3mL	Intramuscular; Subcutaneous	REMEDYREPACK INC.	2021-07-27	Not applicable
Epinephrine	Injection	0.3 mg/0.3mL	Subcutaneous	Lineage Therapeutics	2010-04-01	2018-05-31
Epinephrine	Injection	0.15 mg/0.3mL	Intramuscular; Subcutaneous	A-S Medication Solutions	2019-08-19	Not applicable
Epinephrine	Injection	0.3 mg/1	Subcutaneous	Greenstone, Llc	2010-03-31	2012-09-30
Epinephrine	Injection	0.3 mg/0.3mL	Intramuscular	Medical Purchasing Solutions, Llc	2016-12-15	Not applicable
Epinephrine	Injection	0.3 mg/0.3mL	Subcutaneous	A-S Medication Solutions	2010-04-01	2018-02-28
Epinephrine	Injection	0.3 mg/0.3mL	Intramuscular; Subcutaneous	A-S Medication Solutions	2018-11-27	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Crown-pak Max 4-ply	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1984-03-29	Not applicable
Gingi-pak Cotton Coil	Solution	1.18 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1987-06-26	Not applicable
Gingi-pak Max 2-ply	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1984-03-29	Not applicable
Gingi-pak Max Soft-twist No 1	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1987-06-26	Not applicable
Gingi-pak Max Soft-twist No 2	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1985-01-11	Not applicable
Gingi-pak Max Soft-twist No 3	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1985-01-11	Not applicable
Gingi-pak Max Z-twist No 00	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1995-05-24	Not applicable
Gingi-pak Max Z-twist No 1	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1995-05-24	Not applicable
Gingi-pak Max Z-twist No 2	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1995-05-24	Not applicable
Gingi-pak Max Z-twist No 3	Solution	0.197 mg/10mm	Dental; Oral; Periodontal	Gingi-Pak a Division of the Belport	1995-05-24	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
2% Lidocaine and Epinephrine 1:100,000 Injection USP	Epinephrine (0.01 mg / mL) + Lidocaine hydrochloride (20 mg / mL)	Liquid	Infiltration	Alveda Pharmaceuticals Inc	2008-12-01	Not applicable
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)	Epinephrine (0.005 mg / mL) + Articaine hydrochloride (40 mg / mL)	Solution	Infiltration	Dentsply Pharmaceutical	1997-02-26	2003-11-28
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)	Epinephrine bitartrate (0.005 mg / mL) + Articaine hydrochloride (40 mg / mL)	Solution	Infiltration	Dentsply Pharmaceutical	2004-01-29	Not applicable
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)	Epinephrine bitartrate (0.01 mg / mL) + Articaine hydrochloride (40 mg / mL)	Solution	Infiltration	Dentsply Pharmaceutical	2004-01-29	Not applicable
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)	Epinephrine (0.01 mg / mL) + Articaine hydrochloride (40 mg / mL)	Solution	Infiltration	Dentsply Pharmaceutical	1997-02-26	2003-11-28
4% Citanest Forte Dental With Epinephrine 1:200,000	Epinephrine (0.005 mg / mL) + Prilocaine hydrochloride (40 mg / mL)	Solution	Infiltration	Dentsply Pharmaceutical	2011-01-18	Not applicable
Ana-kit	Epinephrine hydrochloride (1 mg / kit) + Chlorpheniramine maleate (2 mg / kit)	Liquid; Tablet	Intramuscular; Oral; Subcutaneous	Miles Canada Inc. Pharmaceutical Division	1995-12-31	1998-09-25
Ana-kit (2mg/tab Orl, 1mg/ml Liq Sc Im)	Epinephrine (1 mg / kit) + Chlorpheniramine maleate (2 mg / kit)	Liquid; Tablet	Intramuscular; Oral; Subcutaneous	Hollister Stier Laboratories Llc	1997-05-13	2002-09-05
Anakit Insect Sting Treatment Kit	Epinephrine (1 mg / kit) + Chlorpheniramine maleate (2 mg / kit)	Liquid; Tablet	Oral; Parenteral	Hollister Stier, Unit Pharm, Division Of Miles Canada Inc.	1964-12-31	1998-09-25
ANESFAR 40 MG/2 ML + 0.025 MG/2 ML ENJEKSİYONLUK ÇÖZELTİ İÇEREN AMPUL, 20 AMPUL	Epinephrine (0.025 mg/2ml) + Lidocaine hydrochloride (40 mg/2ml)	Injection	Percutaneous	FARMALAS İLAÇ SAN. VE TİC. LTD. ŞTİ.	2020-08-14	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Adrenalin	Epinephrine (1 mg/1mL)	Injection	Intracardiac; Intramuscular; Intraspinal; Intravenous; Subcutaneous	JHP Pharmaceuticals, LLC.	2007-10-01	2013-07-31
Adrenalin	Epinephrine (1 mg/1mL)	Injection	Intracardiac; Intramuscular; Intraspinal; Intravenous; Subcutaneous	JHP Pharmaceuticals, LLC.	2007-10-01	2013-07-31
ADRENALIN 0,25 MG 10 AMPUL	Epinephrine (0.25 mg/mL)	Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	OSEL İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ADRENALIN 0,5 MG 10 AMPUL	Epinephrine (0.5 mg/mL)	Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	OSEL İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ADRENALIN 1 MG 10 AMPUL	Epinephrine (1 mg/mL)	Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	OSEL İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ADRENALIN BAS GALEN 1 MG 10 AMP	Epinephrine (1 mg/mL)	Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	GALEN İLAÇ SAN.VE TİC.A.Ş	2020-08-14	Not applicable
ADRENALIN BAS.GALEN 0,25 MG 10 AMPUL	Epinephrine (0.25 mg/mL)	Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	GALEN İLAÇ SAN.VE TİC.A.Ş	2020-08-14	Not applicable
ADRENALIN COD.GALEN 0,5 MG 10 AMPUL	Epinephrine (0.5 mg/mL)	Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	GALEN İLAÇ SAN.VE TİC.A.Ş	2020-08-14	Not applicable
Adyphren Amp II Kit	Epinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)	Kit	Topical	Asclemed Usa, Inc.	2016-10-27	Not applicable
Adyphren Amp Kit	Epinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)	Kit	Topical	Asclemed Usa, Inc.	2016-10-27	Not applicable

ATC CodesA01AD01 — Epinephrine

A01AD — Other agents for local oral treatment
A01A — STOMATOLOGICAL PREPARATIONS
A01 — STOMATOLOGICAL PREPARATIONS
A — ALIMENTARY TRACT AND METABOLISM

R03AK01 — Epinephrine and other drugs for obstructive airway diseases

R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
R03A — ADRENERGICS, INHALANTS
R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R — RESPIRATORY SYSTEM

B02BC09 — Epinephrine

B02BC — Local hemostatics
B02B — VITAMIN K AND OTHER HEMOSTATICS
B02 — ANTIHEMORRHAGICS
B — BLOOD AND BLOOD FORMING ORGANS

C01CA24 — Epinephrine

C01CA — Adrenergic and dopaminergic agents
C01C — CARDIAC STIMULANTS EXCL. CARDIAC GLYCOSIDES
C01 — CARDIAC THERAPY
C — CARDIOVASCULAR SYSTEM

S01EA01 — Epinephrine

S01EA — Sympathomimetics in glaucoma therapy
S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01 — OPHTHALMOLOGICALS
S — SENSORY ORGANS

R01AA14 — Epinephrine

R01AA — Sympathomimetics, plain
R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
R01 — NASAL PREPARATIONS
R — RESPIRATORY SYSTEM

R03AA01 — Epinephrine

R03AA — Alpha- and beta-adrenoreceptor agonists
R03A — ADRENERGICS, INHALANTS
R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R — RESPIRATORY SYSTEM

S01EA51 — Epinephrine, combinations

S01EA — Sympathomimetics in glaucoma therapy
S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01 — OPHTHALMOLOGICALS
S — SENSORY ORGANS

Drug Categories

Adrenergic Agents
Adrenergic Agonists
Adrenergic alpha-1 Receptor Agonists
Adrenergic alpha-2 Receptor Agonists
Adrenergic alpha-Agonists
Adrenergic and Dopaminergic Agents
Adrenergic beta-1 Receptor Agonists
Adrenergic beta-2 Receptor Agonists
Adrenergic beta-3 Receptor Agonists
Adrenergic beta-Agonists
Adrenergics, Inhalants
Agents producing tachycardia
Agents that produce hypertension
Alpha-and Beta-adrenergic Agonists
Amines
Anti-Asthmatic Agents
Antiglaucoma Preparations and Miotics
Autonomic Agents
Benzene Derivatives
Biogenic Amines
Biogenic Monoamines
Bronchodilator Agents
Cardiac Stimulants Excl. Cardiac Glycosides
Cardiac Therapy
Cardiovascular Agents
Catecholamines
Catechols
COMT Substrates
Cytochrome P-450 CYP2C9 Inhibitors
Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
Cytochrome P-450 CYP3A Inhibitors
Cytochrome P-450 CYP3A4 Inhibitors
Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
Cytochrome P-450 Enzyme Inhibitors
Dental Agents
Drugs for Obstructive Airway Diseases
Epinephrine and similars
Hemostatics
Hyperglycemia-Associated Agents
Local Hemostatics
Mydriatics
Nasal Preparations
Neurotransmitter Agents
OCT1 substrates
OCT2 Inhibitors
OCT2 Substrates
Ophthalmologicals
Peripheral Nervous System Agents
Phenols
Respiratory System Agents
Stomatological Preparations
Sympathomimetic (Adrenergic) Agents
Sympathomimetics
Sympathomimetics in Glaucoma Therapy
Sympathomimetics, Plain
Vasoconstrictor Agents

Chemical TaxonomyProvided by Classyfire DescriptionThis compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.KingdomOrganic compoundsSuper ClassBenzenoidsClassPhenolsSub ClassBenzenediolsDirect ParentCatecholsAlternative ParentsAralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcoholsSubstituents1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Catechol / Hydrocarbon derivativeMolecular FrameworkAromatic homomonocyclic compoundsExternal Descriptorsadrenaline (CHEBI:28918) / Biogenic amines, Adrenalines (C00788) Affected organisms

Humans and other mammals

UNIIYKH834O4BHCAS number51-43-4InChI KeyUCTWMZQNUQWSLP-VIFPVBQESA-NInChI

InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1

IUPAC Name

4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

SMILES

CNC[C@H](O)C1=CC(O)=C(O)C=C1

Synthesis Reference

Pamela Albaugh, "Pharmaceutical epinephrine-pilocarpine compounds and process of preparation thereof." U.S. Patent US5198545, issued October, 1988.

US5198545General References

Yamashima T: Jokichi Takamine (1854-1922), the samurai chemist, and his work on adrenalin. J Med Biogr. 2003 May;11(2):95-102. [Article]
Bennett MR: One hundred years of adrenaline: the discovery of autoreceptors. Clin Auton Res. 1999 Jun;9(3):145-59. [Article]
Otto CW, Yakaitis RW, Blitt CD: Mechanism of action of epinephrine in resuscitation from asphyxial arrest. Crit Care Med. 1981 Apr;9(4):321-4. [Article]
Callaway CW: Epinephrine for cardiac arrest. Curr Opin Cardiol. 2013 Jan;28(1):36-42. doi: 10.1097/HCO.0b013e32835b0979. [Article]
Shao H, Li CS: Epinephrine in Out-of-hospital Cardiac Arrest: Helpful or Harmful? Chin Med J (Engl). 2017 Sep 5;130(17):2112-2116. doi: 10.4103/0366-6999.213429. [Article]
van der Poll T, Coyle SM, Barbosa K, Braxton CC, Lowry SF: Epinephrine inhibits tumor necrosis factor-alpha and potentiates interleukin 10 production during human endotoxemia. J Clin Invest. 1996 Feb 1;97(3):713-9. [Article]
Bjornson C, Russell K, Vandermeer B, Klassen TP, Johnson DW: Nebulized epinephrine for croup in children. Cochrane Database Syst Rev. 2013 Oct 10;(10):CD006619. doi: 10.1002/14651858.CD006619.pub3. [Article]
Teva Pharmaceuticals USA gained approval to market its generic epinephrine auto-injector in 0.3 mg and 0.15 mg strengths. [Link]
Epinephrine, by Injection: NIH [Link]
Symjepi Approval History [Link]
FDA approves Auvi-Q [Link]
Epipen.ca [Link]
Medicines UK document [Link]
Croup: American Family Physician Document [Link]
NIH STAT pearls [Link]
PubChem: Epinephrine [Link]
FDA Approved Drug Products: ADRENALIN (epinephrine injection) 1 mg/mL, for intramuscular, subcutaneous, and intravenous use [Link]
Epinephrine FDA label [File]
Primatene Prescribing Info [File]
Pfizer Monograph [File]

External LinksHuman Metabolome DatabaseHMDB0000068KEGG DrugD00095KEGG CompoundC00788PubChem Compound5816PubChem Substance46509097ChemSpider5611BindingDB44818RxNav3992ChEBI28918ChEMBLCHEMBL679ZINCZINC000000039089Therapeutic Targets DatabaseDAP000066PharmGKB PA449470Guide to PharmacologyGtP Drug PagePDBe LigandALERxListRxList Drug PageDrugs.comDrugs.com Drug PageWikipediaAdrenalinePDB Entries2hkk / 4a7u / 4ldo / 7brn / 7btsFDA labelMSDSClinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Anesthesia Morbidity / Anesthetics Adverse Reaction / Dental Implant Failed / Surgical Complications From Local Anesthesia	1
4	Active Not Recruiting	Treatment	Rotator Cuff Injuries / Rotator Cuff Tears / Subacromial Impingement / Subacromial Impingement Syndrome	1
4	Active Not Recruiting	Treatment	Varicosities of the great saphenous vein	1
4	Completed	Not Available	Anaesthesia / Nerve Block / Orthopaedic Disorders	1
4	Completed	Basic Science	Pain	1
4	Completed	Diagnostic	Arrhythmia / Local Anaesthesia therapy / Renal Cancers / Surgery	1
4	Completed	Diagnostic	Free Flaps / Head and Neck Carcinoma / Hypotension / Oral Cancers	1
4	Completed	Health Services Research	Bronchiolitis	1
4	Completed	Health Services Research	Effect of Drugs / Tooth Extractions	1
4	Completed	Other	Chronic Sinusitis	1

Manufacturers

Sterling health div sterling winthrop inc
Armstrong pharmaceuticals inc
Wyeth consumer healthcare
Shionogi pharma inc
Meridian medical technologies inc
Forest laboratories inc
3m pharmaceuticals inc
Astrazeneca lp
Pharmaton ltd
Dentsply pharmaceutical

Packagers

Adamis Laboratories
Amend
American Regent
Amphastar Pharmaceuticals
APP Pharmaceuticals
Armstrong Pharmaceuticals Inc.
A-S Medication Solutions LLC
AstraZeneca Inc.
Baroli
Bayer Healthcare
Belport Co. Inc.
Bioniche Pharma
Cardinal Health
Carestream Health Inc.
Catalent Pharma Solutions
Claris Lifesciences Inc.
Cura Pharmaceutical Co. Inc.
DENTSPLY International
Deproco Inc.
Dey Pharma LP
Eastman Kodak Co. Dental Products
General Injectables and Vaccines Inc.
Greenstone LLC
Henry Schein Inc.
Hikma Pharmaceuticals
Hollister-Stier Laboratories LLC
Hospira Inc.
JHP Pharmaceuticals LLC
Jordan Pharmaceuticals Inc.
Luitpold Pharmaceuticals Inc.
Mckesson Corp.
Medical Products Laboratories Inc.
Meridian Medical Technologies Inc.
Monarch Pharmacy
Nephro-Tech Inc.
North Safety Products
Novocol Pharmaceutical Canada
Pascal Co. Inc.
Pharmedium
Phillips Medical
Physicians Total Care Inc.
Prescript Pharmaceuticals
Professional Co.
Prometic Pharma Inc.
Sciele Pharma Inc.
Septodont Inc.
Shionogi Pharma Inc.
Sintetica SA
Smiths Medical ASD Inc.
Taylor Pharmaceuticals
Verus Pharmaceuticals Inc.
Walgreen Co.
West-Ward Pharmaceuticals
Wyeth Pharmaceuticals

Dosage Forms

Form	Route	Strength
Injection	Intramuscular; Subcutaneous	1 mg/1mL
Solution	Intramuscular	0.15 mg / 0.15 mL
Solution	Intramuscular	0.30 mg / 0.30 mL
Injection	Intracardiac; Intramuscular; Intraspinal; Intravenous; Subcutaneous	1 mg/1mL
Injection	Intramuscular; Intraocular; Subcutaneous	1 mg/1mL
Injection	Intramuscular; Intravenous; Subcutaneous	1 mg/1mL
Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous
Injection, solution	Parenteral
Solution	Topical	1 mg / mL
Solution	Intravenous; Subcutaneous	1 mg
Solution	Intramuscular; Intravenous; Subcutaneous	1 mg
Injection, solution	Intravenous
Injection, solution	Parenteral	0.5 MG/ML
Injection, solution	Parenteral	1 MG/ML
Injection, solution
Injection	Intramuscular; Intravenous; Subcutaneous	1 mg/ml
Kit	Intramuscular; Intraocular; Subcutaneous
Injection, solution	Dental
Solution	Intramuscular	0.3 mg / 0.3 mL
Liquid; tablet	Intramuscular; Oral; Subcutaneous
Liquid; tablet	Oral; Parenteral
Injection, solution		0.3 ml
Injection	Percutaneous
Injection	Infiltration; Submucosal
Injection, solution	Dental; Infiltration
Injection, solution	Submucosal	0.01 mg
Injection	Intramuscular; Subcutaneous	.15 mg/1
Injection	Intramuscular; Subcutaneous	0.3 mg/1
Injection, solution	Intramuscular	0.1 mg/0.1mL
Injection, solution	Intramuscular	0.15 mg/0.15mL
Injection, solution	Intramuscular	0.3 mg/0.3mL
Aerosol, metered	Respiratory (inhalation)	0.5 %
Injection, solution	Epidural; Infiltration; Intracaudal
Injection, solution	Epidural; Infiltration; Intracaudal; Perineural
Injection, solution	Parenteral	150 MICROGRAMMI/0.3ML
Injection, solution	Parenteral	300 MICROGRAMMI/0.3ML
Injection, solution	Parenteral	500 MICROGRAMMI/0.3ML
Injection, solution	Submucosal
Injection, solution	Parenteral
Injection	Dental	40 mg/ml
Kit	Intravenous
Injection, solution; kit; solution	Epidural; Infiltration; Intracaudal; Perineural; Topical
Spray	Respiratory (inhalation)	3.5 %
Solution / drops	Ophthalmic
Injection, solution	Intragingival
Injection	Dental	20 mg/ml
Injection, solution	Ophthalmic
Solution	Intramuscular	0.5 mg / 0.5 mL
Injection, solution	Intravenous	0.1 mg/1mL
Liquid	Intramuscular	0.3 mg / 0.3 mL
Injection
Injection	Intracardiac; Intravenous	0.1 mg/1mL
Injection	Intramuscular; Subcutaneous	0.15 mg/0.3mL
Injection	Parenteral	0.1 mg/1mL
Injection	Parenteral	1 mg/1mL
Injection	Subcutaneous	0.15 mg/1
Injection	Subcutaneous	0.15 mg/0.15mL
Injection	Subcutaneous	0.3 mg/1
Injection	Subcutaneous	0.3 mg/0.3mL
Injection, solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	1 mg/1mL
Injection, solution	Endotracheal; Intracardiac; Intravenous	0.1 mg/1mL
Injection, solution	Intracardiac; Intramuscular; Intravenous; Subcutaneous	1 mg/1mL
Injection, solution	Intracardiac; Intravenous	0.1 mg/1mL
Injection, solution	Intramuscular; Intravenous; Subcutaneous	1 mg/1mL
Injection, solution	Intramuscular; Subcutaneous	1 mg/1mL
Injection, solution	Subcutaneous	1 mg/1mL
Injection, solution, concentrate	Intravenous	1 mg/1mL
Liquid	Intramuscular	1 mg / mL
Solution	Nasal	1 mg/1mL
Injection; kit; swab	Intramuscular; Subcutaneous; Topical
Liquid	Intracardiac; Intravenous	.1 mg / mL
Solution	Intramuscular; Intravenous; Subcutaneous	1 mg / mL
Solution	Intravenous	1 mg / 10 mL
Solution	Endotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous	1 mg / 1 mL
Solution	Endotracheal; Intramuscular; Intravenous; Subcutaneous	1 mg / 1 mL
Solution	Intracardiac; Intravenous	1 mg / 10 mL
Solution	Intramuscular; Intravenous; Subcutaneous	1 mg / 1 mL
Kit	Intramuscular; Subcutaneous
Injection; kit	Intramuscular; Subcutaneous; Topical
Kit	Intramuscular; Subcutaneous	1 mg/1mL
Injection	Intramuscular	0.3 mg/0.3mL
Injection, solution	Intramuscular
Injection		0.3 mg
Injection, solution	Parenteral	300 Mikrogramm
Injection	Intramuscular	0.15 mg/0.3mL
Solution	Intramuscular	0.15 mg / 0.3 mL
Injection		0.15 mg
Solution		0.5 mg/1ml
Injection, solution	Parenteral	150 Mikrogramm
Injection	Intramuscular; Subcutaneous	1 mg/1000mL
Kit	Topical
Solution	Dental
Packing	Dental	.5 mg / 2.54 cm
Solution	Dental; Oral; Periodontal	1.18 mg/10mm
Solution	Dental; Oral; Periodontal	0.197 mg/10mm
Solution	Dental; Oral; Periodontal	0.7 mg/1
Solution
Injection, solution	Parenteral	150 MICROGRAMMI
Injection, solution	Parenteral	300 MICROGRAMMI
Solution	Endotracheal; Intravenous	2 mg/20ml
Solution	Parenteral
Injection, solution	Subcutaneous
Injection	Epidural; Infiltration; Intracaudal; Perineural
Solution	Epidural; Infiltration
Injection, solution	Epidural
Injection, solution	Epidural; Infiltration
Injection, solution	Infiltration
Injection, solution
Patch	Iontophoresis
Solution	Intramuscular
Liquid	Infiltration
Injection	Intravascular; Intravenous
Injection	Epidural
Liquid	Epidural; Infiltration
Aerosol	Respiratory (inhalation)	0.16 ug/1
Spray	Topical
Solution	Topical
Gel	Topical
Injection	Dental	0.01 mg/mL
Liquid	Dental; Subcutaneous
Liquid	Subcutaneous
Injection
Solution	Dental; Oral; Periodontal	1200 mg/15mL
Injection, solution	Intramuscular	1 mg/ml
Solution	Parenteral	1 mg
Injection, solution	Dental	40 mg/ml
Aerosol	Respiratory (inhalation)	125 ug/1
Inhalant	Oral	0.22 mg/1
Capsule	Respiratory (inhalation)	0.22 mg/1
Kit	Respiratory (inhalation)	0.22 mg/1
Injection, solution; kit; solution	Infiltration; Perineural; Topical
Injection, solution	Buccal
Solution	Infiltration
Injection	Intramuscular	18 mcg/1.8ml
Injection, solution	Perineural
Injection, solution	Epidural; Intracaudal; Perineural
Injection, solution	Epidural; Retrobulbar
Injection	Epidural; Parenteral
Injection	Epidural; Parenteral; Retrobulbar
Solution	Infiltration	0.009 mg
Injection, solution	Infiltration; Submucosal
Kit	Infiltration; Topical
Liquid	Parenteral; Topical
Injection, solution	Endotracheal; Intramuscular; Intravenous; Subcutaneous	1 mg/ml
Injection	Dental	5 mg
Injection	Intramuscular; Subcutaneous	0.3 mg/0.3mL
Injection, solution	Intramuscular; Subcutaneous	0.15 mg/0.3mL
Injection, solution	Intramuscular; Subcutaneous	0.3 mg/0.3mL
Solution	Intramuscular; Subcutaneous	0.15 mg / 0.15 mL
Solution	Intramuscular; Subcutaneous	0.3 mg / 0.3 mL
Injection	Submucosal	40 mg/ml
Solution
Injection, solution	Submucosal	0.0125 mg/ml
Injection	Parenteral
Injection, solution	Interstitial
Injection	Submucosal	0.0125 mg/ml
Injection	Infiltration
Injection, solution	Infiltration; Perineural
Solution	Epidural
Injection	Dental	0.0125 mg/ml
Liquid	Epidural
Injection	Dental
Solution		1 mg/1ml

Prices

Unit description	Cost	Unit
Twinject 2 0.3 mg/dose Device One Box Contains 2 Syringes	200.43USD	box
Epinephrine hcl powder	189.0USD	g
EpiPen 2-Pak (1 Package = 2 Syringes) Package	155.13USD	package
EpiPen Jr 2-Pak (1 Package = 2 Syringes) Package	155.13USD	package
Twinject 0.15 mg/dose Device Syringe	104.14USD	syringe
Epipen 0.3 mg/syr Syringe	93.04USD	syringe
Epipen Jr 0.15 mg/syr Syringe	93.04USD	syringe
Twinject 0.15 mg auto-injector	86.63USD	each
Twinject Auto Injector 0.15 mg/syr Syringe	84.85USD	syringe
Twinject Auto Injector 0.3 mg/syr Syringe	84.85USD	syringe
EpiPen (single Syringe) Syringe	77.56USD	syringe
EpiPen Jr (single Syringe) Syringe	77.56USD	syringe
Epipen jr 0.15 mg auto-inject	74.58USD	each
Epinephrine 0.3 mg auto-inject	67.05USD	each
Nephron FA 100 tablet Box	49.99USD	box
Epipen 0.3 mg auto-injector	41.78USD	each
Epinephrine powder	4.68USD	g
Epinephrine bitartrate crys	4.2USD	g
Adrenalin 1 mg/ml ampul	2.93USD	ml
Epinephrine 1 mg/ml ampul	2.9USD	ml
Adrenalin cl 1 mg/ml vial	1.42USD	ml
Epinephrine 0.1 mg/ml syringe	1.32USD	ml
Primatene mist inhaler	1.0USD	ml
Adrenalin 1:1000 nasal soln	0.83USD	ml
Bronchial mist inhaler	0.8USD	ml
Primatene mist inh refill	0.68USD	ml
Adrenalin 1 mg/ml	0.62USD	ml
Adrenalin 1 mg/ml Solution	0.61USD	ml
Nephron fa tablet	0.44USD	each
Epinephrine 1 mg/ml vial	0.18USD	ml
Bronkaid dual action caplet	0.14USD	caplet
Epinephrine-d5w 2 mg/250 ml	0.07USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5665071	No	1997-09-09	2013-05-27
US7794432	No	2010-09-14	2025-09-11
US8870827	No	2014-10-28	2025-09-11
US7449012	No	2008-11-11	2025-09-11
US8048035	No	2011-11-01	2025-09-11
US7297136	No	2007-11-20	2025-01-18
US7621891	No	2009-11-24	2025-02-04
US6629968	No	2003-10-07	2020-06-30
US6635045	No	2003-10-21	2021-06-29
US9149579	No	2015-10-06	2025-07-19
US8425462	No	2013-04-23	2024-11-23
US8231573	No	2012-07-31	2028-11-25
US8016788	No	2011-09-13	2025-03-21
US9259539	No	2016-02-16	2026-02-01
US8206360	No	2012-06-26	2027-02-27
US9238108	No	2016-01-19	2027-01-22
US8226610	No	2012-07-24	2029-04-10
US7918823	No	2011-04-05	2024-11-23
US8608698	No	2013-12-17	2024-11-23
US8021344	No	2011-09-20	2029-11-02
US8361029	No	2013-01-29	2024-11-23
US8313466	No	2012-11-20	2024-11-23
US7731690	No	2010-06-08	2025-01-15
US9278182	No	2016-03-08	2026-02-01
US8920377	No	2014-12-30	2024-11-23
US7731686	No	2010-06-08	2026-06-01
US8926594	No	2015-01-06	2026-03-31
US7749194	No	2010-07-06	2028-10-30
US9056170	No	2015-06-16	2024-11-23
US7947017	No	2011-05-24	2028-03-12
US9295657	No	2016-03-29	2035-03-13
US9119876	No	2015-09-01	2035-03-13
US9283197	No	2016-03-15	2034-08-15
US9586010	No	2017-03-07	2025-09-11
US7905352	No	2011-03-15	2027-04-12
US9724471	No	2017-08-08	2027-05-23
US9737669	No	2017-08-22	2024-11-23
US9833573	No	2017-12-05	2024-11-23
US10039728	No	2018-08-07	2034-08-14
US10004700	No	2018-06-26	2034-08-14
US10130592	No	2018-11-20	2035-03-13
US8367734	No	2013-02-05	2026-01-26
US10314977	No	2019-06-11	2024-11-23
US10335549	No	2019-07-02	2025-04-30
US10166344	No	2019-01-01	2025-01-21
US10166334	No	2019-01-01	2025-01-21
US10737028	No	2020-08-11	2024-11-23
US10688244	No	2020-06-23	2037-12-21
US10842938	No	2020-11-24	2037-12-21
US10960155	No	2021-03-30	2026-06-25
US11141540	No	2016-10-20	2036-10-20

StateSolidExperimental Properties

Property	Value	Source
melting point (°C)	211.5	https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine
boiling point (°C)	215	MSDS
water solubility	less than 0.1 mg/mL at 64° F	https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Melting-Point
logP	-1.37	https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Vapor-Pressure
Caco2 permeability	-6.02	https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Stability
pKa	8.59 (at 25 °C)	https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Stability

Predicted Properties

Property	Value	Source
Water Solubility	18.6 mg/mL	ALOGPS
logP	-0.82	ALOGPS
logP	-0.43	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å2	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.23 m3·mol-1	ChemAxon
Polarizability	19.04 Å3	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9934
Blood Brain Barrier	-	0.966
Caco-2 permeable	-	0.8958
P-glycoprotein substrate	Substrate	0.5953
P-glycoprotein inhibitor I	Non-inhibitor	0.9036
P-glycoprotein inhibitor II	Non-inhibitor	0.8465
Renal organic cation transporter	Non-inhibitor	0.8903
CYP450 2C9 substrate	Non-substrate	0.7897
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.6928
CYP450 1A2 substrate	Non-inhibitor	0.7862
CYP450 2C9 inhibitor	Non-inhibitor	0.9563
CYP450 2D6 inhibitor	Non-inhibitor	0.9638
CYP450 2C19 inhibitor	Non-inhibitor	0.9451
CYP450 3A4 inhibitor	Non-inhibitor	0.9121
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9516
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.9322
Biodegradation	Ready biodegradable	0.6459
Rat acute toxicity	2.3715 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7514
hERG inhibition (predictor II)	Non-inhibitor	0.7961

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Mass Spec (NIST)Not AvailableSpectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	GC-MS	splash20-014i-0900000000-5ca773e378035e522e65
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash20-014i-0900000000-5ca773e378035e522e65
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	LC-MS/MS	splash20-014i-0900000000-7718bec49c1a109083e5
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	LC-MS/MS	splash20-0a4i-4900000000-ec5581e838e2a4a66139
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	LC-MS/MS	splash20-004i-9200000000-4572448ba3dadff2d2a6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	LC-MS/MS	splash20-001i-0900000000-9da12d9c8551de2507be
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	LC-MS/MS	splash20-03di-0900000000-12dd42d00be1feb2ea6f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	LC-MS/MS	splash20-00di-0900000000-57c9bc614d9bbbfeed6b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	LC-MS/MS	splash20-00dj-0900000000-375b0df9797eb0a3db5f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	LC-MS/MS	splash20-0fdk-1900000000-04c230e802b08770ccd4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	LC-MS/MS	splash20-014i-0900000000-b707acd2982b875d2b8a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	LC-MS/MS	splash20-014i-0900000000-f3590054822872902032
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	LC-MS/MS	splash20-0a4i-1900000000-7d7916641e9f2b8c2a1d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	LC-MS/MS	splash20-0adi-8900000000-5bbc248c0ddc66e4fe40
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	LC-MS/MS	splash20-004i-9300000000-af8ce8ce2cdd535404e9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	LC-MS/MS	splash20-0159-0900000000-f2fafb87963f9f1c6960
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	LC-MS/MS	splash20-0uxr-2900000000-b54ca44315664cba912a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	LC-MS/MS	splash20-0udi-4900000000-881b25fed45874c66e13
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	LC-MS/MS	splash20-0ugi-9500000000-1fadd0dd0beb4816b39d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	LC-MS/MS	splash20-004j-9000000000-61011b8f179c08d62b62
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash20-03di-0900000000-32c82b77af021d75c50c
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash20-03di-0900000000-01e028bfa6568f5b6c73
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash20-03k9-0900000000-a6ef0d80ad589128e08c
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash20-00di-0900000000-40299b1fe53fcb9eecd0
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash20-00dj-0900000000-86d7c17c9ef430bd35b3
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash20-00dj-0900000000-1804022689692d453a61
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash20-001i-0900000000-9da12d9c8551de2507be
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash20-03di-0900000000-12dd42d00be1feb2ea6f
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash20-00di-0900000000-c14c5838cb37fa872ab3
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash20-00dj-0900000000-375b0df9797eb0a3db5f
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash20-0fdk-1900000000-04c230e802b08770ccd4
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash20-014i-0900000000-a6d3f1554e198f6a8f03
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash20-014i-0900000000-764cb0c1210c346e8bd3
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash20-014i-0900000000-474addf762a49be24ee7
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash20-0a4i-1900000000-ac89b65a526c832307e0
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash20-0ab9-3900000000-683ba244d13e2d75c306
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash20-05i0-5900000000-5cdca096026d6d3b9207
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-014i-0900000000-b707acd2982b875d2b8a
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-014i-0900000000-11cde2cb09790e4e65cf
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-0a4i-1900000000-a1e4933b8de2ad37fc1a
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-0adi-8900000000-618cea43e6fe3e029eb0
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-004i-9300000000-77667b55ec8b2d2f01a9
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-0159-0900000000-d6da72693f2867eafeeb
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-0uxr-2900000000-b54ca44315664cba912a
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-0udi-4900000000-ddb658c2925f26d0d038
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-0ugi-9500000000-1fadd0dd0beb4816b39d
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash20-004j-9000000000-61011b8f179c08d62b62
MS/MS Spectrum - , positive	LC-MS/MS	splash20-014i-0900000000-501938a09fca0bf8890f
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Targets

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KindProteinOrganismHumansPharmacological action

Yes

Actions

Agonist

General FunctionProtein heterodimerization activitySpecific FunctionThis alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...Gene NameADRA1AUniprot IDP35348Uniprot NameAlpha-1A adrenergic receptorMolecular Weight51486.005 Da

References

Sanbe A, Tanaka Y, Fujiwara Y, Tsumura H, Yamauchi J, Cotecchia S, Koike K, Tsujimoto G, Tanoue A: Alpha1-adrenoceptors are required for normal male sexual function. Br J Pharmacol. 2007 Oct;152(3):332-40. Epub 2007 Jul 2. [Article]
Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [Article]
Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [Article]
Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [Article]

KindProteinOrganismHumansPharmacological action

Yes

Actions

Agonist

General FunctionProtein heterodimerization activitySpecific FunctionThis alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...Gene NameADRA1BUniprot IDP35368Uniprot NameAlpha-1B adrenergic receptorMolecular Weight56835.375 Da

References

Cotecchia S: The alpha1-adrenergic receptors: diversity of signaling networks and regulation. J Recept Signal Transduct Res. 2010 Dec;30(6):410-9. doi: 10.3109/10799893.2010.518152. Epub 2010 Oct 18. [Article]
Shieh JP, Chu CC, Wang JJ, Lin MT: Epinephrine, phenylephrine, and methoxamine induce infiltrative anesthesia via alpha1-adrenoceptors in rats. Acta Pharmacol Sin. 2009 Sep;30(9):1227-36. doi: 10.1038/aps.2009.129. [Article]
Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [Article]
Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [Article]

KindProteinOrganismHumansPharmacological action

Yes

Actions

Agonist

General FunctionReceptor signaling protein activitySpecific FunctionBeta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...Gene NameADRB1Uniprot IDP08588Uniprot NameBeta-1 adrenergic receptorMolecular Weight51322.1 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [Article]
Khasar SG, McCarter G, Levine JD: Epinephrine produces a beta-adrenergic receptor-mediated mechanical hyperalgesia and in vitro sensitization of rat nociceptors. J Neurophysiol. 1999 Mar;81(3):1104-12. doi: 10.1152/jn.1999.81.3.1104. [Article]
Strosberg AD: Structure, function, and regulation of adrenergic receptors. Protein Sci. 1993 Aug;2(8):1198-209. doi: 10.1002/pro.5560020802. [Article]

KindProteinOrganismHumansPharmacological action

Yes

Actions

Agonist

General FunctionProtein homodimerization activitySpecific FunctionBeta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...Gene NameADRB2Uniprot IDP07550Uniprot NameBeta-2 adrenergic receptorMolecular Weight46458.32 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [Article]
Prenner L, Sieben A, Zeller K, Weiser D, Haberlein H: Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy. Biochemistry. 2007 May 1;46(17):5106-13. Epub 2007 Apr 7. [Article]
Lucin KM, Sanders VM, Jones TB, Malarkey WB, Popovich PG: Impaired antibody synthesis after spinal cord injury is level dependent and is due to sympathetic nervous system dysregulation. Exp Neurol. 2007 Sep;207(1):75-84. Epub 2007 Jun 2. [Article]
Reiner S, Ambrosio M, Hoffmann C, Lohse MJ: Differential signaling of the endogenous agonists at the beta2-adrenergic receptor. J Biol Chem. 2010 Nov 12;285(46):36188-98. doi: 10.1074/jbc.M110.175604. Epub 2010 Sep 13. [Article]

KindProteinOrganismHumansPharmacological action

Yes

Actions

Agonist

General FunctionThioesterase bindingSpecific FunctionAlpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...Gene NameADRA2AUniprot IDP08913Uniprot NameAlpha-2A adrenergic receptorMolecular Weight48956.275 Da

References

Nyronen T, Pihlavisto M, Peltonen JM, Hoffren AM, Varis M, Salminen T, Wurster S, Marjamaki A, Kanerva L, Katainen E, Laaksonen L, Savola JM, Scheinin M, Johnson MS: Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine. Mol Pharmacol. 2001 May;59(5):1343-54. [Article]
MacLennan SJ, Reynen PH, Martin RS, Eglen RM, Martin GR: Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using extracellular acidification rate changes. Br J Pharmacol. 2000 Apr;129(7):1333-8. [Article]
Hieble JP, Hehr A, Li YO, Ruffolo RR Jr: Molecular basis for the stereoselective interactions of catecholamines with alpha-adrenoceptors. Proc West Pharmacol Soc. 1998;41:225-8. [Article]
Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [Article]
Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. doi: 10.1002/med.20134. [Article]
Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [Article]
Ariens EJ, Simonis AM: Physiological and pharmacological aspects of adrenergic receptor classification. Biochem Pharmacol. 1983 May 15;32(10):1539-45. [Article]

Kind ProteinOrganismHumansPharmacological action

Yes

Actions

Agonist

General FunctionEpinephrine bindingSpecific FunctionAlpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...Gene NameADRA2BUniprot IDP18089Uniprot NameAlpha-2B adrenergic receptorMolecular Weight49565.8 Da

References

Gobbi M, Frittoli E, Mennini T: The modulation of [3H]noradrenaline and [3H]serotonin release from rat brain synaptosomes is not mediated by the alpha 2B-adrenoceptor subtype. Naunyn Schmiedebergs Arch Pharmacol. 1990 Oct;342(4):382-6. [Article]
Vizi ES, Katona I, Freund TF: Evidence for presynaptic cannabinoid CB(1) receptor-mediated inhibition of noradrenaline release in the guinea pig lung. Eur J Pharmacol. 2001 Nov 16;431(2):237-44. [Article]
Rudling JE, Richardson J, Evans PD: A comparison of agonist-specific coupling of cloned human alpha(2)-adrenoceptor subtypes. Br J Pharmacol. 2000 Nov;131(5):933-41. [Article]
Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [Article]
Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [Article]
Ariens EJ, Simonis AM: Physiological and pharmacological aspects of adrenergic receptor classification. Biochem Pharmacol. 1983 May 15;32(10):1539-45. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Actions

Antagonist

General Function Alpha1-adrenergic receptor activitySpecific FunctionThis alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.Gene NameADRA1DUniprot IDP25100Uniprot NameAlpha-1D adrenergic receptorMolecular Weight 60462.205 Da

References

Cotecchia S: The alpha1-adrenergic receptors: diversity of signaling networks and regulation. J Recept Signal Transduct Res. 2010 Dec;30(6):410-9. doi: 10.3109/10799893.2010.518152. Epub 2010 Oct 18. [Article]
Shieh JP, Chu CC, Wang JJ, Lin MT: Epinephrine, phenylephrine, and methoxamine induce infiltrative anesthesia via alpha1-adrenoceptors in rats. Acta Pharmacol Sin. 2009 Sep;30(9):1227-36. doi: 10.1038/aps.2009.129. [Article]
Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [Article]
Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Actions

Antagonist

Agonist

General FunctionTumor necrosis factor receptor bindingSpecific FunctionCytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...Gene NameTNFUniprot IDP01375Uniprot NameTumor necrosis factorMolecular Weight25644.15 Da

References

van der Poll T, Coyle SM, Barbosa K, Braxton CC, Lowry SF: Epinephrine inhibits tumor necrosis factor-alpha and potentiates interleukin 10 production during human endotoxemia. J Clin Invest. 1996 Feb 1;97(3):713-9. [Article]
Liao J, Keiser JA, Scales WE, Kunkel SL, Kluger MJ: Role of epinephrine in TNF and IL-6 production from isolated perfused rat liver. Am J Physiol. 1995 Apr;268(4 Pt 2):R896-901. doi: 10.1152/ajpregu.1995.268.4.R896. [Article]

Enzymes

KindProteinOrganismHumansPharmacological action

Unknown

Actions

Inhibitor

Data based on findings of in vitro studies.

General FunctionSteroid hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...Gene NameCYP2C9Uniprot IDP11712Uniprot NameCytochrome P450 2C9Molecular Weight55627.365 Da

References

Gervasini G, Martinez C, Benitez J, Agundez JA: Effect of neurotransmitters on NADPH-cytochrome P450 reductase in vitro activity. Drug Metab Lett. 2007 Aug;1(3):172-5. [Article]
Gervasini G, Martinez C, Agundez JA, Garcia-Gamito FJ, Benitez J: Inhibition of cytochrome P450 2C9 activity in vitro by 5-hydroxytryptamine and adrenaline. Pharmacogenetics. 2001 Feb;11(1):29-37. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Actions

Inhibitor

Enzyme action supported only by one in vitro study.

General FunctionVitamin d3 25-hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...Gene NameCYP3A4Uniprot IDP08684Uniprot NameCytochrome P450 3A4Molecular Weight57342.67 Da

References

Gervasini G, Martinez C, Benitez J, Agundez JA: Effect of neurotransmitters on NADPH-cytochrome P450 reductase in vitro activity. Drug Metab Lett. 2007 Aug;1(3):172-5. [Article]

KindProteinOrganismHumansPharmacological action

Actions

Substrate

General FunctionO-methyltransferase activitySpecific FunctionCatalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...Gene NameCOMTUniprot IDP21964Uniprot NameCatechol O-methyltransferaseMolecular Weight30036.77 Da

References

Bryan-Lluka LJ, O'Donnell SR: Dopamine and adrenaline, but not isoprenaline, are substrates for uptake and metabolism in isolated perfused lungs of rats. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jul;346(1):20-6. [Article]
Eisenhofer G, Finberg JP: Different metabolism of norepinephrine and epinephrine by catechol-O-methyltransferase and monoamine oxidase in rats. J Pharmacol Exp Ther. 1994 Mar;268(3):1242-51. [Article]
Medicines UK document [Link]

KindProtein groupOrganismHumansPharmacological action

Unknown

Actions

Substrate

General FunctionSerotonin bindingSpecific FunctionCatalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...

Components:

References

Bryan-Lluka LJ, O'Donnell SR: Dopamine and adrenaline, but not isoprenaline, are substrates for uptake and metabolism in isolated perfused lungs of rats. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jul;346(1):20-6. [Article]
Eisenhofer G, Finberg JP: Different metabolism of norepinephrine and epinephrine by catechol-O-methyltransferase and monoamine oxidase in rats. J Pharmacol Exp Ther. 1994 Mar;268(3):1242-51. [Article]
Medicines UK document [Link]

Transporters

KindProteinOrganismHumansPharmacological action

Unknown

Actions

Substrate

General FunctionQuaternary ammonium group transmembrane transporter activitySpecific FunctionMediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...Gene NameSLC22A2Uniprot IDO15244Uniprot NameSolute carrier family 22 member 2Molecular Weight62579.99 Da

References

Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [Article]
Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [Article]
Jonker JW, Wagenaar E, Van Eijl S, Schinkel AH: Deficiency in the organic cation transporters 1 and 2 (Oct1/Oct2 [Slc22a1/Slc22a2]) in mice abolishes renal secretion of organic cations. Mol Cell Biol. 2003 Nov;23(21):7902-8. [Article]

KindProteinOrganismHumansPharmacological action

Unknown

Actions

Substrate

General FunctionSecondary active organic cation transmembrane transporter activitySpecific FunctionTranslocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...Gene NameSLC22A1 Uniprot IDO15245Uniprot NameSolute carrier family 22 member 1Molecular Weight61153.345 Da

References

Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [Article]
Breidert T, Spitzenberger F, Grundemann D, Schomig E: Catecholamine transport by the organic cation transporter type 1 (OCT1). Br J Pharmacol. 1998 Sep;125(1):218-24. [Article]

Drug created at June 13, 2005 13:24 / Updated at October 25, 2022 10:47

What is the mechanism of action of norepinephrine?

Mechanism of action/pharmacology Noradrenaline is a vasoconstrictor that predominantly stimulates α₁ receptors to cause peripheral vasoconstriction and increase blood pressure. It also has some β₁ receptor agonist activity that results in a positive inotropic effect on the heart at higher doses.

How does norepinephrine increase heart rate?

Norepinephrine promotes vasoconstriction, which is a narrowing of the blood vessels. This, in turn, increases blood pressure. Like epinephrine, norepinephrine also stimulates alpha-adrenoreceptors in the cells of the blood vessels. It increases heart rate and blood sugar levels.

Which vasoconstrictor is usually associated with the treatment of anaphylaxis?

Epinephrine is the medication of choice for the first-aid treatment of anaphylaxis. Through vasoconstrictor effects, it prevents or decreases upper airway mucosal edema (laryngeal edema), hypotension, and shock. In addition, it has important bronchodilator effects and cardiac inotropic and chronotropic effects.

What receptors does epinephrine work?

Epinephrine is a sympathomimetic catecholamine that exerts its pharmacologic effects on both alpha and beta-adrenergic receptors using a G protein-linked second messenger system. It has a greater affinity for beta receptors in small doses. However, large doses produce selective action on alpha receptors.