Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0590)
Drug Name
Epinephrine hydrochloride
Synonyms
Epinephrine HCl; Epinephrine chloride; Epinephrine hydrochloride; Epinephrine, hydrochloride; GELATIN; Gelatin-epinephrine; Supranephrin solution; Suprarenin hydrochloride; UNII-WBB047OO38; l-Adrenaline chloride; l-Adrenaline hydrochloride; l-Epinephrine chloride; l-Epinephrine hydrochloride; l-Epinephrine.HCl; Epinephrine; Epirenamine; L-(+)-Adrenaline; Medihaler-Epi; NA71GR3TNV; NSC62786; Racepinefrine, (S)-; Suprarenin; UNII-NA71GR3TNV; Vaponefrin; d-Adrenaline; l-Suprarenin; (+)-adrenaline; (S)-(+)-adrenaline; (S)-4-(1-Hydroxy-2-(methylamino)ethyl)pyrocatechol; (S)-adrenaline; 1,2-Benzenediol,4-[(1S)-1-hydroxy-2-(methylamino)ethyl]-; 1-Adrenaline; 1-Epirenamine; 150-05-0; 4-[(1S)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol; ADR ADRENALINE; BRN 2938799; CHEBI:40751; CHEMBL42280; D-Epifrin; D-Epinephrine; EINECS 205-752-5; 1-Epinephrine hydrochloride; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol hydrochloride; 55-31-2; Adrenalin chloride; Adrenalin hydrochloride; Adrenaline chloride; Adrenaline hydrochloride; CCRIS 2368
Indication Allergy [ICD11: 4A80] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 219.66 Topological Polar Surface Area 72.7
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
441411
ChEBI ID
CHEBI:6213
CAS Number
55-31-2
TTD Drug ID
D04PHC
Formula
C9H14ClNO3
Canonical SMILES
CNCC(C1=CC(=C(C=C1)O)O)O.Cl
InChI
1S/C9H13NO3.ClH/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;/h2-4,9-13H,5H2,1H3;1H/t9-;/m0./s1
InChIKey
ATADHKWKHYVBTJ-FVGYRXGTSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Dihydroxymandelic acid DM001921
85782
Unclear 1 [2]
Epinephrine glucuronide metabolite DM001919
53480450
Conjugation - Glucuronidation 1 [8]
Epinephrine sulfate metabolite DM001918
3035453
Conjugation - Sulfation 1 [4]
Metanephrine DM001920
21100
Conjugation - O-Methylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002846 Epinephrine hydrochloride Epinephrine sulfate metabolite Conjugation - Sulfation SULT1A3 [4]
MR002847 Epinephrine hydrochloride Epinephrine glucuronide metabolite Conjugation - Glucuronidation UGT1A1 [8]
MR002848 Epinephrine hydrochloride Metanephrine Conjugation - O-Methylation COMT [2]
MR002849 Epinephrine hydrochloride Dihydroxymandelic acid Unclear MAO-A [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[2]
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[3]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[4]
Thiopurine methyltransferase (TPMT) DME0014 Homo sapiens
TPMT_HUMAN
2.1.1.67
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6]
Unclear metabolic mechanism (DME-unclear) DME1443 Odoribacter laneus Not Available Not Available [7]
⏷ Show the Full List of 6  DME(s)
References
1 Epinephrine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Role of monoamine-oxidase-A-gene variation in the development of glioblastoma in males: a case control study. J Neurooncol. 2019 Nov;145(2):287-294.
4 Crystal structure of human sulfotransferase SULT1A3 in complex with dopamine and 3'-phosphoadenosine 5'-phosphate. Biochem Biophys Res Commun. 2005 Sep 23;335(2):417-23.
5 Adrenal catecholamines and their metabolism in the vitamin A deficient rat. Ann Nutr Metab. 1983;27(3):220-7.
6 Steroid glucuronides: human circulatory levels and formation by LNCaP cells. J Steroid Biochem Mol Biol. 1991;40(4-6):593-8.
7 Alistipes indistinctus sp. nov. and Odoribacter laneus sp. nov., common members of the human intestinal microbiota isolated from faeces. Int J Syst Evol Microbiol. 2010 Jun;60(Pt 6):1296-302.
8 LABEL:?ARTICAINE HYDROCHLORIDE AND EPINEPHRINE injection, solution

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