U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO3
Molecular Weight 183.2048
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPINEPHRINE

SMILES

CNC[C@@]([H])(c1ccc(c(c1)O)O)O

InChI

InChIKey=UCTWMZQNUQWSLP-VIFPVBQESA-N
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

HIDE SMILES / InChI
Epinephrine is a sympathomimetic catecholamine. It acts as a naturally occurring agonist at both alpha and beta-adrenergic receptors. Three pharmacologic types have been identified: alpha 1-, alpha 2-, and beta-adrenergic receptors. Each of these has three subtypes, characterized by both structural and functional differences. The alpha 2 and beta receptors are coupled negatively and positively, respectively, to adenylyl cyclase via Gi or Gs regulatory proteins, and the alpha 1 receptors modulate phospholipase C via the Go protein. Subtype expression is regulated at the level of the gene, the mRNA, and the protein through various transcriptional and postsynthetic mechanisms. Through its action on alpha-adrenergic receptors, epinephrine lessens the vasodilation and increased vascular permeability that occurs during anaphylaxis, which can lead to loss of intravascular fluid volume and hypotension. Through its action on beta-adrenergic receptors, epinephrine causes bronchial smooth muscle relaxation and helps alleviate bronchospasm, wheezing and dyspnea that may occur during anaphylaxis. Epinephrine also alleviates pruritus, urticaria, and angioedema and may relieve gastrointestinal and genitourinary symptoms associated with anaphylaxis because of its relaxer effects on the smooth muscle of the stomach, intestine, uterus and urinary bladder. Epinephrine increases glycogenolysis, reduces glucose up take by tissues, and inhibits insulin release in the pancreas, resulting in hyperglycemia and increased blood lactic acid.

Originator

Curator's Comment:: Characterized some of the physical and biochemical properties of adrenal extract and laid the platform for purification of the active substance which was first achieved by John Abel in 1899 at Johns Hopkins University, Baltimore and independently by the Japanese scientist Jokichi Takamine in his own laboratory in New York City with the sponsorship of Parke-Davis & Co., and Thomas Aldrich (Parke-Davis & Co., Detroit, Michigan).

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ADRENALIN

Approved Use

Adrenalin® is a non-selective alpha and beta adrenergic agonist indicated for:  Emergency treatment of allergic reactions (Type 1), including anaphylaxis  Induction and maintenance of mydriasis during intraocular surgery
Preventing
ADRENALIN

Approved Use

Adrenalin® is a non-selective alpha and beta adrenergic agonist indicated for:  Emergency treatment of allergic reactions (Type 1), including anaphylaxis  Induction and maintenance of mydriasis during intraocular surgery
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
309 pg/mL
0.3 mg single, intramuscular
dose: 0.3 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
EPINEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
386 pg/mL
5 mg multiple, nasal
dose: 5 mg
route of administration: Nasal
experiment type: MULTIPLE
co-administered:
EPINEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.486 ng/mL
0.3 mg single, intramuscular
dose: 0.3 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
EPINEPHRINE unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
18.3 ng × min/mL
0.3 mg single, intramuscular
dose: 0.3 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
EPINEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
19.4 ng × min/mL
5 mg multiple, nasal
dose: 5 mg
route of administration: Nasal
experiment type: MULTIPLE
co-administered:
EPINEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.724 ng × h/mL
0.3 mg single, intramuscular
dose: 0.3 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
EPINEPHRINE unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.3 mg 1 times / day single, intramuscular
Recommended
Dose: 0.3 mg, 1 times / day
Route: intramuscular
Route: single
Dose: 0.3 mg, 1 times / day
Sources: Page: nda/2012/201739Orig1s000MedR.pdf - p.55
healthy, 18 to 45 years old
n = 66
Health Status: healthy
Age Group: 18 to 45 years old
Sex: M+F
Population Size: 66
Sources: Page: nda/2012/201739Orig1s000MedR.pdf - p.55
Disc. AE: Ventricular extrasystoles...
AEs leading to
discontinuation/dose reduction:
Ventricular extrasystoles (grade 1, 1.5%)
Sources: Page: nda/2012/201739Orig1s000MedR.pdf - p.55
AEs

AEs

AESignificanceDosePopulation
Ventricular extrasystoles grade 1, 1.5%
Disc. AE
0.3 mg 1 times / day single, intramuscular
Recommended
Dose: 0.3 mg, 1 times / day
Route: intramuscular
Route: single
Dose: 0.3 mg, 1 times / day
Sources: Page: nda/2012/201739Orig1s000MedR.pdf - p.55
healthy, 18 to 45 years old
n = 66
Health Status: healthy
Age Group: 18 to 45 years old
Sex: M+F
Population Size: 66
Sources: Page: nda/2012/201739Orig1s000MedR.pdf - p.55
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
PubMed

PubMed

TitleDatePubMed
Effects of succinylcholine and d-tubocurarine on epinephrine-induced arrhythmias during halothane anesthesia in dogs.
1975 Jan
[Experimental anti-arrhythmic effects of a new beta-adrenergic receptor blocking agent, dl-l-(tert. butylamino)-3-[(2-propinyloxy)phenoxy]2-propanol hydrochloride (dl Kö 1400-Cl)].
1976 Jul
Attenuation of catecholamine-induced immunosuppression in whole blood from patients with sepsis.
1999 Dec
gamma2-COP, a novel imprinted gene on chromosome 7q32, defines a new imprinting cluster in the human genome.
1999 Dec
Pulpal ischemia in man: effects on detection threshold, A-delta neural response and sharp dental pain.
1999 Feb
Hypotensive effect of tenuifolic saponin and its mechanism.
1999 Jul
Biological effects of Myristica fragrans (nutmeg) extract.
1999 Jun
Landiolol decreases a dysrhythmogenic dose of epinephrine in dogs during halothane anesthesia.
1999 Jun
Ephedrine-induced complete atrioventricular block with ventricular asystole during rapid concomitant phenytoin infusion: a case report.
1999 Mar
[Distributive shock and it's therapy by cardio-vascular acting drugs].
1999 Oct
Influences of catecholamines on the sudden death induced in dogs by an antifungal agent, D0870.
2000 Apr
Central retinal artery occlusion after a local anesthetic with adrenaline on nasal mucosa.
2000 Dec
Low catecholamine concentrations protect adult rat ventricular myocytes against apoptosis through cAMP-dependent extracellular signal-regulated kinase activation.
2000 Dec
Carvedilol prevents epinephrine-induced apoptosis in human coronary artery endothelial cells: modulation of Fas/Fas ligand and caspase-3 pathway.
2000 Feb
Seizure suppression by systemic epinephrine is mediated by the vagus nerve.
2000 Feb
[Lactic acidosis: a complication of spinal cord injury in multiple trauma].
2000 Jun
Cardiovascular studies on different classes of soft drugs.
2000 Mar
Influence of antioxidants on blood-brain barrier permeability during adrenaline-induced hypertension.
2000 Nov
Circulatory support of the sick preterm infant.
2001 Feb
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
Partial agonist clonidine mediates alpha(2)-AR subtypes specific regulation of cAMP accumulation in adenylyl cyclase II transfected DDT1-MF2 cells.
2001 Feb
The effects of epidural block on the distribution of lymphocyte subsets and natural-killer cell activity in patients with and without pain.
2001 Feb
Plasma catecholamine and cardiovascular responses to physostigmine in Alzheimer's disease and aging.
2001 Feb
Changes in the derived central pressure waveform and pulse pressure in response to angiotensin II and noradrenaline in man.
2001 Feb 1
Adenosine diphosphate strongly potentiates the ability of the chemokines MDC, TARC, and SDF-1 to stimulate platelet function.
2001 Feb 15
Key role of the P2Y(1) receptor in tissue factor-induced thrombin-dependent acute thromboembolism: studies in P2Y(1)-knockout mice and mice treated with a P2Y(1) antagonist.
2001 Feb 6
Early neurohormonal effects of trandolapril in patients with left ventricular dysfunction and a recent acute myocardial infarction: a double-blind, randomized, placebo-controlled multicentre study.
2001 Jan
Alterations in myocardial creatinine kinase (CK) and lactate dehydrogenase (LDH) isoenzyme-distribution in a model of left ventricular dysfunction.
2001 Jan
Influence of ABO blood groups on primary hemostasis.
2001 Jan
Contrasting clinical properties and exercise responses in obese and lean hypertensive patients.
2001 Jan
Guanabenz, an antihypertensive centrally acting alpha2-agonist, suppresses morning elevations in aggregation of human platelets.
2001 Jan
Regulation of endothelin-1 production in cultured rat vascular smooth muscle cells.
2001 Jan
Plasma concentrations and pharmacokinetics of bupivacaine with and without adrenaline following caudal anaesthesia in infants.
2001 Jan
The PlA polymorphism of glycoprotein IIIa functions as a modifier for the effect of estrogen on platelet aggregation.
2001 Jan
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine.
2001 Jan
Effects of high extracellular [K+] and adrenaline on force development, relaxation and membrane potential in cardiac muscle from freshwater turtle and rainbow trout.
2001 Jan
Catecholamine responses to alpha-adrenergic blockade during exercise in women acutely exposed to altitude.
2001 Jan
Clonidine combined with a long acting local anesthetic does not prolong postoperative analgesia after brachial plexus block but does induce hemodynamic changes.
2001 Jan
Hypoxic vasoconstriction of cyclostome systemic vessels: the antecedent of hypoxic pulmonary vasoconstriction?
2001 Jan
A single bout of exercise induces beta-adrenergic desensitization in human adipose tissue.
2001 Jan
Lack of effect of incretin hormones on insulin release from pancreatic islets in the bile duct-ligated rats.
2001 Jan
Synthesis and characterization of an immobilized phenylethanolamine N-methyltransferase liquid chromatographic stationary phase.
2001 Jan 1
Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci.
2001 Jan 15
Epinephrine upregulates superoxide dismutase in human coronary artery endothelial cells.
2001 Jan 15
Hyperinsulinemia and autonomic nervous system dysfunction in obesity: effects of weight loss.
2001 Jan 30
Effect of amlodipine on cardiopulmonary performance in volunteers.
2001 Jan-Feb
Patents

Patents

Sample Use Guides

Anaphylaxis: o Adults and Children 30 kg (66 lbs) or more: 0.3 to 0.5 mg (0.3 to 0.5 mL) intramuscularly or subcutaneously into anterolateral aspect of the thigh every 5 to 10 minutes as necessary o Children 30 kg (66 lbs) or less: 0.01 mg/kg (0.01 mL/kg), up to 0.3 mg (0.3 mL), intramuscularly or subcutaneously into anterolateral aspect of the thigh every 5 to 10 minutes as necessary (2.1) Intraocular surgery: Dilute 1 mL with 100 to 1000 mL of an ophthalmic irrigation fluid, for ophthalmic irrigation or intracameral injection
Route of Administration: Other
Treatment of primary human hepatocytes with 10μM epinephrine for 24h repressed mRNA expression of various transporters, such as the sinusoidal influx transporters NTCP, OATP1B1, OATP2B1, OAT2, OAT7 and OCT1 and the efflux transporters MRP2, MRP3 and BSEP, whereas it induced that of MDR1, but failed to alter that of BCRP.
Name Type Language
EPINEPHRINE
HSDB   INN   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
LIDOSITE TOPICAL SYSTEM KIT COMPONENT EPINEPHRINE
Common Name English
EPINEPHRINE COMPONENT OF OCTOCAINE
Common Name English
EPINEPHRINE [USP]
Common Name English
NSC-62786
Code English
EPINEPHRINUM [WHO-IP LATIN]
Common Name English
NEPHRIDINE
Common Name English
EPINEPHRINE [MI]
Common Name English
EPINEPHRINE [ORANGE BOOK]
Common Name English
BRONKAID MIST
Brand Name English
ADRENALINE [EP MONOGRAPH]
Common Name English
EPINEPHRINE COMPONENT OF IONTOCAINE
Common Name English
EPINEPHRINE [WHO-IP]
Common Name English
ADRENALINE [EP]
Common Name English
ANAPEN
Brand Name English
ADRENALINE [JAN]
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-, (R)-
Common Name English
SUS-PHRINE
Brand Name English
EPINEPHRINE [USP-RS]
Common Name English
ADRENALIN
Systematic Name English
IONTOCAINE COMPONENT EPINEPHRINE
Common Name English
EPINEPHRINE [INN]
Common Name English
SUS-PHRINE SULFITE-FREE
Brand Name English
SUS-PHRINE SULPHITE-FREE
Common Name English
(-)-(R)-EPINEPHRINE
Common Name English
(-)-EPINEPHRINE
Common Name English
EPINEPHRINE [WHO-DD]
Common Name English
SUSPHRINE
Brand Name English
OCTOCAINE COMPONENT EPINEPHRINE
Common Name English
(-)-3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)BENZYL ALCOHOL
Systematic Name English
ADRENALINE
EP   MART.  
Systematic Name English
SYMJEPI
Brand Name English
EPINEPHRINE [HSDB]
Common Name English
ADRENALINUM
HPUS  
Common Name English
EPINEPHRINE COMPONENT OF LIDOSITE TOPICAL SYSTEM KIT
Common Name English
TWINJECT
Brand Name English
RACEPINEFRINE, (R)-
Common Name English
BENZYL ALCOHOL, 3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (-)-
Systematic Name English
4-((1R)-1-HYDROXY-2-(METHYLAMINO)ETHYL)-1,2-BENZENEDIOL
Systematic Name English
GLAUPOSINE
Common Name English
ADRENALINE [MART.]
Common Name English
EPIPEN
Brand Name English
ADRENALINUM [HPUS]
Common Name English
PRIMATENE MIST
Brand Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 1.2 (LID/EPI)
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
NDF-RT N0000175552
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WHO-ESSENTIAL MEDICINES LIST 21.5
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WHO-VATC QB02BC09
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LOINC 13735-6
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LOINC 33874-9
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WHO-ATC C01CA24
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
CFR 21 CFR 346.12
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WHO-ATC S01EA01
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WHO-VATC QS01EA01
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LOINC 14711-6
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LOINC 2230-1
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NDF-RT N0000175570
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LOINC 2232-7
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WHO-VATC QC01CA24
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WHO-ATC B02BC09
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WHO-VATC QR03AK01
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FDA ORPHAN DRUG 134800
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WHO-ESSENTIAL MEDICINES LIST 03
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LOINC 13734-9
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LOINC 16111-7
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WHO-ESSENTIAL MEDICINES LIST 25.1
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NDF-RT N0000175555
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
CFR 21 CFR 341.16
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LOINC 24521-7
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WHO-ESSENTIAL MEDICINES LIST 12.2
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LOINC 2231-9
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LOINC 44837-3
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NDF-RT N0000000209
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LOINC 25908-5
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WHO-ATC R03AK01
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LOINC 11046-0
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NDF-RT N0000000245
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WHO-VATC QR03AA01
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WHO-ATC R01AA14
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WHO-VATC QR01AA14
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WHO-VATC QA01AD01
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LOINC 14712-4
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WHO-ATC S01EA51
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NDF-RT N0000007715
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LOINC 49552-3
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WHO-ATC A01AD01
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FDA ORPHAN DRUG 133200
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LOINC 24522-5
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LOINC 25909-3
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LOINC 32015-0
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WHO-ATC R03AA01
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LOINC 43248-4
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NCI_THESAURUS C88516
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Code System Code Type Description
CAS
51028-73-0
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
SUPERSEDED
WIKIPEDIA
EPINEPHRINE
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
EPA CompTox
51-43-4
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
DRUG BANK
DB00668
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
EVMPD
SUB06568MIG
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL679
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
RXCUI
3992
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY RxNorm
MESH
D004837
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
DRUG CENTRAL
1028
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
EVMPD
SUB130356
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
ALTERNATIVE
NCI_THESAURUS
C473
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
HSDB
4289
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PRIMARY
IUPHAR
479
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PRIMARY
FDA UNII
YKH834O4BH
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PRIMARY
MERCK INDEX
M4944
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-098-7
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
USP_CATALOG
1236970
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY USP-RS
LACTMED
Epinephrine
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
PUBCHEM
5816
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EPINEPHRINE
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY Other name: Adrenaline. (In certain countries the name Adrenaline is a trademark. In those countries this name may be used onlywhen applied to the product issued by the owners of the trademark.)Description: A white or almost white, microcrystalline powder; odourless.Solubility: Very slightly soluble in water; practically insoluble in ethanol (~750 g/l) TS, ether R and acetone R.Category: Sympathomimetic.Storage: Epinephrine should be kept in a hermetically closed container, protected from light.Additional information: Epinephrine gradually darkens in colour on exposure to air and light. Even in the absence of light,Epinephrine is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.RequirementsDefinition: Epinephrine contains not less than 98.5% and not more than 101.0% of C9H13NO3, calculated with reference to thedried substance.
INN
2142
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY
CAS
51-43-4
Created by admin on Fri Jun 25 21:11:24 UTC 2021 , Edited by admin on Fri Jun 25 21:11:24 UTC 2021
PRIMARY