Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13NO3.C6H8O6 |
Molecular Weight | 359.3285 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO.CNC[C@H](O)C2=CC=C(O)C(O)=C2
InChI
InChIKey=KOUXVSUXTJGEEM-GJZRPOMESA-N
InChI=1S/C9H13NO3.C6H8O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;7-1-2(8)5-3(9)4(10)6(11)12-5/h2-4,9-13H,5H2,1H3;2,5,7-10H,1H2/t9-;2-,5+/m00/s1
Molecular Formula | C9H13NO3 |
Molecular Weight | 183.2044 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C6H8O6 |
Molecular Weight | 176.1241 |
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2331074 |
|||
Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9003072 |
33.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ADRENALIN Approved UseAdrenalin® 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 UseAdrenalin® 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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
309 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26994624 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26994624 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.3 ng × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26994624 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26994624 |
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
Dose | Population | Adverse 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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/19356039/ Page: 2.0 |
yes [Ki 156 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19356039/ Page: 2.0 |
yes [Ki 42.3 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19356039/ Page: 2.0 |
yes [Ki 707 uM] | |||
Page: 8.0 |
yes | |||
Page: 8.0 |
yes | |||
Page: 8.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
More Horner's than meets the eye. | 2000 |
|
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 |
|
Effects of ubiquinone-10 on energy metabolism and lipid peroxidation in rats with myocardial ischemia. | 2000 Jul |
|
[Lactic acidosis: a complication of spinal cord injury in multiple trauma]. | 2000 Jun |
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Cardiovascular studies on different classes of soft drugs. | 2000 Mar |
|
[Acute toxic accident following lumbar plexus block with bupivacaine]. | 2000 May |
|
Beta-adrenergic modulation of NNK-induced lung carcinogenesis in hamsters. | 2000 Nov |
|
Influence of antioxidants on blood-brain barrier permeability during adrenaline-induced hypertension. | 2000 Nov |
|
Enabling sutureless vascular bypass grafting with the exovascular sleeve anastomosis. | 2000 Sep |
|
The effects of epidural block on the distribution of lymphocyte subsets and natural-killer cell activity in patients with and without pain. | 2001 Feb |
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[(123)I]metaiodobenzylguanidine and [(111)In]octreotide uptake in begnign and malignant pheochromocytomas. | 2001 Feb |
|
Plasma catecholamine and cardiovascular responses to physostigmine in Alzheimer's disease and aging. | 2001 Feb |
|
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 |
|
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 |
|
Hormonal responses to exercise in chronic fatigue syndrome. | 2001 Jan |
|
Genitourinary injuries in the newborn. | 2001 Jan |
|
Fatalities due to anaphylactic reactions to foods. | 2001 Jan |
|
Viral croup. | 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 |
|
Development of glaucoma after phacoemulsification for removal of cataracts in dogs: 22 cases (1987-1997). | 2001 Jan 1 |
|
Synthesis and characterization of an immobilized phenylethanolamine N-methyltransferase liquid chromatographic stationary phase. | 2001 Jan 1 |
|
Embryonic epinephrine synthesis in the rat heart before innervation: association with pacemaking and conduction tissue development. | 2001 Jan 19 |
|
The role of nitric oxide in bradycardia of rats with obstructive cholestasis. | 2001 Jan 5 |
|
Mice with a deletion in the gene for CCAAT/enhancer-binding protein beta have an attenuated response to cAMP and impaired carbohydrate metabolism. | 2001 Jan 5 |
|
Effect of amlodipine on cardiopulmonary performance in volunteers. | 2001 Jan-Feb |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28603032
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
Edited
Sat Dec 16 10:58:30 GMT 2023
by
admin
on
Sat Dec 16 10:58:30 GMT 2023
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Record UNII |
QH0PJV94AX
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Record Status |
Validated (UNII)
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Record Version |
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-
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69652297
Created by
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62265-31-0
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DTXSID80928379
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134-17-8
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NON-SPECIFIC STEREOCHEMISTRY | |||
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QH0PJV94AX
Created by
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