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

General Information of Drug (ID: DR0564)
Drug Name
Eletriptan hydrobromide
Synonyms
Eletriptan (hydrobromide); Eletriptan HBr; Eletriptan Hydrobromide [USAN]; Eletriptan hydrobromide; Eletriptan; Eletriptan [INN:BAN]; NCGC00181130-01; Relpax; UK 116044; UK-116044; UK-116044-04; UK-116044-04 [As Hydrobromide); UNII-22QOO9B8KI; (R)-3-((1-methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole; 143322-58-1; 22QOO9B8KI; 3-(((R)-1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)indole; 5-[2-(benzenesulfonyl)ethyl]-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole; 5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole; CHEBI:50922; DSSTox_RID_81968; M41W832TA3; UK 116044-04; UNII-M41W832TA3; Eletriptan monohydrobromide; (R)-3-((1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole monohydrobromide; (R)-3-((1-Methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole hydrobromide; 177834-92-3; 3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole Hydrobromide; CHEBI:61176
Indication Migraine [ICD11: 8A80] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 463.4 Topological Polar Surface Area 61.6
Heavy Atom Count 28 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
656631
ChEBI ID
CHEBI:61176
CAS Number
177834-92-3
TTD Drug ID
D02DMQ
Formula
C22H27BrN2O2S
Canonical SMILES
CN1CCCC1CC2=CNC3=C2C=C(C=C3)CCS(=O)(=O)C4=CC=CC=C4.Br
InChI
1S/C22H26N2O2S.BrH/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20;/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3;1H/t19-;/m1./s1
InChIKey
UTINOWOSWSPFLJ-FSRHSHDFSA-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
Eletriptan N-Oxide DM000573
29979307
Oxidation - N-oxidation 1 [4]
N-Desmethyl eletriptan DM000572
22873800
Oxidation - N-demethylation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006849 Eletriptan hydrobromide N-Desmethyl eletriptan Oxidation - N-demethylation CYP2D6 ... [3]
MR006850 Eletriptan hydrobromide Eletriptan N-Oxide Oxidation - N-oxidation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[4]
References
1 Eletriptan Hydrobromide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response. Ther Adv Neurol Disord. 2016 Sep;9(5):414-23.
3 Eletriptan metabolism by human hepatic CYP450 enzymes and transport by human P-glycoprotein. Drug Metab Dispos. 2003 Jul;31(7):861-9.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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