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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO3
Molecular Weight 183.2044
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPINEPHRINE

SMILES

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

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

Molecular Formula C9H13NO3
Molecular Weight 183.2044
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
33.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ADRENALIN
Preventing
ADRENALIN

Cmax

ValueDoseCo-administeredAnalytePopulation
309 pg/mL
0.3 mg single, intramuscular
EPINEPHRINE plasma
Homo sapiens
386 pg/mL
5 mg multiple, nasal
EPINEPHRINE plasma
Homo sapiens
0.486 ng/mL
0.3 mg single, intramuscular
EPINEPHRINE unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
18.3 ng × min/mL
0.3 mg single, intramuscular
EPINEPHRINE plasma
Homo sapiens
19.4 ng × min/mL
5 mg multiple, nasal
EPINEPHRINE plasma
Homo sapiens
0.724 ng × h/mL
0.3 mg single, intramuscular
EPINEPHRINE unknown
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
YKH834O4BH
Record Status Validated (UNII)
Record Version