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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO3.C4H6O6
Molecular Weight 333.2918
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPINEPHRINE BITARTRATE

SMILES

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

InChI

InChIKey=YLXIPWWIOISBDD-NDAAPVSOSA-N
InChI=1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula C9H13NO3
Molecular Weight 183.2048
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O6
Molecular Weight 150.087
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
The incidence of systemic side-effects following subconjunctival Mydricaine no. 1 injection.
1999 Dec
Hypotensive effect of tenuifolic saponin and its mechanism.
1999 Jul
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
Reversible catecholamine-induced cardiomyopathy by subcutaneous injections of epinephrine solution in an anesthetized patient.
2000 Feb
Disturbed neuroendocrine-immune interactions in chronic fatigue syndrome.
2000 Feb
Seizure suppression by systemic epinephrine is mediated by the vagus nerve.
2000 Feb
Acute renal failure and rhabdomyolysis after inadvertent intra-arterial infusion of excessive doses of epinephrine during cardiopulmonary resuscitation.
2000 Feb 25
Effects of ubiquinone-10 on energy metabolism and lipid peroxidation in rats with myocardial ischemia.
2000 Jul
Beta-adrenergic modulation of NNK-induced lung carcinogenesis in hamsters.
2000 Nov
[(123)I]metaiodobenzylguanidine and [(111)In]octreotide uptake in begnign and malignant pheochromocytomas.
2001 Feb
Oral glucose augments the counterregulatory hormone response during insulin-induced hypoglycemia in humans.
2001 Feb
Troglitazone amplifies counterregulatory responses to hypoglycemia in nondiabetic subjects.
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
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
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
Effects of human pregnancy on cardiac autonomic function above and below the ventilatory threshold.
2001 Jan
Catecholamine responses to alpha-adrenergic blockade during exercise in women acutely exposed to altitude.
2001 Jan
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium.
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
Dexamethasone facilitates discharge after outpatient anorectal surgery.
2001 Jan
Cardiac resuscitation after incremental overdosage with lidocaine, bupivacaine, levobupivacaine, and ropivacaine in anesthetized dogs.
2001 Jan
Neurotransmitter release from bovine adrenal chromaffin cells is modulated by capacitative Ca(2+)entry driven by depleted internal Ca(2+)stores.
2001 Jan
Neonatal catecholamine levels and neurodevelopmental outcome: a cohort study.
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
An accidental ringblock of the great toe?
2001 Jan
Chromaffin-adrenocortical cell interactions: effects of chromaffin cell activation in adrenal cell cocultures.
2001 Jan
Lack of effect of incretin hormones on insulin release from pancreatic islets in the bile duct-ligated rats.
2001 Jan
Reference intervals for glucose, beta-cell polypeptides, and counterregulatory factors during prolonged fasting.
2001 Jan
Cardiovascular effects of hypercarbia in rainbow trout (Oncorhynchus mykiss): a role for externally oriented chemoreceptors.
2001 Jan
Neuroendocrine responses to experimentally-induced psychological stress in healthy humans.
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
Embryonic epinephrine synthesis in the rat heart before innervation: association with pacemaking and conduction tissue development.
2001 Jan 19
Hyperinsulinemia and autonomic nervous system dysfunction in obesity: effects of weight loss.
2001 Jan 30
The role of nitric oxide in bradycardia of rats with obstructive cholestasis.
2001 Jan 5
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:03:42 UTC 2021
Edited
by admin
on Fri Jun 25 21:03:42 UTC 2021
Record UNII
30Q7KI53AK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPINEPHRINE BITARTRATE
JAN   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
EPINEPHRINE BITARTRATE [WHO-DD]
Common Name English
ADRENALINE (AS TARTRATE)
Common Name English
EPINEPHRINE BITARTRATE COMPONENT OF LIGNOSPAN FORTE
Common Name English
EPINEPHRINE BITARTRATE [JAN]
Common Name English
EPINEPHRINE D-BITARTRATE [MI]
Common Name English
ADRENALIN TARTRATE [WHO-IP]
Common Name English
(-)-3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)BENZYL ALCOHOL (+)-TARTRATE (1:1) SALT.
Common Name English
ADRENALINE TARTRATE [EP MONOGRAPH]
Common Name English
ADRENALINE ACID TARTRATE [MART.]
Common Name English
MEDIHALER-EPI
Brand Name English
EPINEPHRINE BITARTRATE [ORANGE BOOK]
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-, (R)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)
Common Name English
EPINEPHRINE HYDROGEN TARTRATE [WHO-IP]
Common Name English
NSC-756755
Code English
EPINEPHRINE BITARTRATE [VANDF]
Common Name English
ADRENALINE TARTRATE
EP  
Systematic Name English
LIGNOSPAN FORTE COMPONENT EPINEPHRINE BITARTRATE
Common Name English
EPINEPHRINI HYDROGENOTARTRAS [WHO-IP LATIN]
Common Name English
BRONITIN
Brand Name English
EPINEPHRINE TARTRATE
Common Name English
ADRENALINE ACID TARTRATE
MART.  
Common Name English
EPINEPHRINE BITARTRATE [USP MONOGRAPH]
Common Name English
EPINEPHRINE BITARTRATE [USP-RS]
Common Name English
ADRENALINE BITARTATE
Common Name English
L-EPINEPHRINE HYDROGEN TARTRATE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 341.16
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
NCI_THESAURUS C87053
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
Code System Code Type Description
MERCK INDEX
M4944
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
EPINEPHRINE BITARTRATE
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY Other name: Adrenalin tartrate. (In certain countries the name Adrenalin is a trademark: In those countries this name may beused only when applied to the product issued by the owners of the trademark.)Description: A white to greyish white, crystalline powder; odourless.Solubility: Soluble in 3 parts of water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R.Category. Sympathomimetic.Storage: Epinephrine hydrogen tartrate should be kept in a tightly closed container, protected from light.Additional information: Epinephrine hydrogen tartrate gradually darkens in colour on exposure to air and light. Even in theabsence of light, Epinephrine hydrogen tartrate is gradually degraded on exposure to a humid atmosphere, the decompositionbeing faster at higher temperatures.Definition: Epinephrine hydrogen tartrate contains not less than 98.0% and not more than 101.0% of C9H13NO3,C4H6O6,calculated with reference to the dried substance.
USP_CATALOG
1237000
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
200-097-1
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
DRUG BANK
DBSALT000788
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
FDA UNII
30Q7KI53AK
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
CAS
51-42-3
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
EVMPD
SUB01911MIG
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
RXCUI
203180
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY RxNorm
EVMPD
SUB72751
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
EPA CompTox
51-42-3
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL679
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
NCI_THESAURUS
C48021
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
PUBCHEM
5815
Created by admin on Fri Jun 25 21:03:42 UTC 2021 , Edited by admin on Fri Jun 25 21:03:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity E by 0.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity D by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY