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

General Information of Drug (ID: DR0148)
Drug Name
BMS-650032
Synonyms
Asunaprevir; Asunaprevir (BMS-650032); Asunaprevir [USAN:INN]; S9X0KRJ00S; Sunvepra (TN); 2R9; 630420-16-5; BMS 650032; BMS-650032; N-(Tert-Butoxycarbonyl)-3-Methyl-L-Valyl-(4r)-4-[(7-Chloro-4-Methoxyisoquinolin-1-Yl)oxy]-N-{(1r,2s)-1-[(Cyclopropylsulfonyl)carbamoyl]-2-Ethenylcyclopropyl}-L-Prolinamide; UNII-S9X0KRJ00S; tert-butyl N-[(1S)-1-[(2S,4R)-4-[(7-chloro-4-methoxy-1-isoquinolyl)oxy]-2-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]carbamoyl]pyrrolidine-1-carbonyl]-2,2-dimethyl-propyl]carbamate
Indication Viral hepatitis [ICD11: 1E51] Phase 3 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 748.3 Topological Polar Surface Area 191
Heavy Atom Count 51 Rotatable Bond Count 14
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
16076883
PubChem SID
24721638 ; 28688599 ; 29960656 ; 81082068 ; 99431640 ; 135316582 ; 135626812 ; 139010040 ; 152258574 ; 160647409 ; 160692698 ; 174315703 ; 198943682 ; 198993976 ; 210024640 ; 210024643 ; 223435540 ; 223715301 ; 224325540 ; 228723059 ; 242681705
ChEBI ID
CHEBI:134723
CAS Number
630420-16-5
TTD Drug ID
D04MCY
Formula
C35H46ClN5O9S
Canonical SMILES
CC(C)(C)C(C(=O)N1CC(CC1C(=O)NC2(CC2C=C)C(=O)NS(=O)(=O)C3CC3)OC4=NC=C(C5=C4C=C(C=C5)Cl)OC)NC(=O)OC(C)(C)C
InChI
1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
InChIKey
XRWSZZJLZRKHHD-WVWIJVSJSA-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
Asunaprevir metabolite M10 DM002499
57945188
Hydrolysis - Hydrolysis 1 [5] , [6]
Asunaprevir metabolite M15 DM002502 N. A. Unclear 1 [5] , [6]
Asunaprevir metabolite M2 DM002500
129107443
Hydrolysis - Hydrolysis 1 [5] , [6]
Asunaprevir metabolite M3,5,7 DM002501 N. A. Oxidation - Monohydroxylation 1 [5] , [6]
Asunaprevir metabolite M6 DM002491 N. A. Oxidation - O-Demethylation 1 [5] , [6]
Asunaprevir metabolite M8 DM002495
166451458
Oxidation - Hydroxylation 1 [5] , [6]
BMS-798430 DM002497 N. A. Reduction - Reduction 1 [5] , [6]
Asunaprevir metabolite M11,19,20 DM002496 N. A. Oxidation - Hydroxylation 2 [5] , [6]
Asunaprevir metabolite M9 DM002492 N. A. Oxidation - Oxidation 2 [5] , [6]
BMS-558364 DM002498 N. A. Hydrolysis - Hydrolysis 2 [5] , [6]
Asunaprevir metabolite M12 DM002493
166451437
Unclear 3 [5] , [6]
Asunaprevir metabolite M25,26 DM002494 N. A. Unclear 3 [5] , [6]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000389 BMS-650032 Asunaprevir metabolite M6 Oxidation - O-Demethylation CYP3A4 ... [5], [6]
MR000390 BMS-650032 Asunaprevir metabolite M8 Oxidation - Hydroxylation Unclear [5], [6]
MR000391 BMS-650032 BMS-798430 Reduction - Reduction Unclear [5], [6]
MR000392 BMS-650032 Asunaprevir metabolite M10 Hydrolysis - Hydrolysis Unclear [5], [6]
MR000393 BMS-650032 Asunaprevir metabolite M2 Hydrolysis - Hydrolysis Unclear [5], [6]
MR000394 BMS-650032 Asunaprevir metabolite M3,5,7 Oxidation - Monohydroxylation CYP3A4 ... [5], [6]
MR000395 BMS-650032 Asunaprevir metabolite M15 Unclear Unclear [5], [6]
MR000384 Asunaprevir metabolite M6 Asunaprevir metabolite M9 Oxidation - Oxidation CYP3A4 ... [5], [6]
MR000386 Asunaprevir metabolite M8 Asunaprevir metabolite M11,19,20 Oxidation - Hydroxylation Unclear [5], [6]
MR000387 BMS-798430 BMS-558364 Hydrolysis - Hydrolysis Unclear [5], [6]
MR000388 Asunaprevir metabolite M10 Asunaprevir metabolite M25,26 Unclear Unclear [5], [6]
MR000385 Asunaprevir metabolite M9 Asunaprevir metabolite M12 Unclear Unclear [5], [6]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
⏷ Show the Full List of 7  DME(s)
References
1 2011 Pipeline of Bristol-Myers Squibb.
2 Australian Public Assessment Report for asunaprevir.
3 Asunaprevir: a review of preclinical and clinical pharmacokinetics and drug-drug interactions. Clin Pharmacokinet. 2015 Dec;54(12):1205-22.
4 Characterization of ADME properties of [(14)C]asunaprevir (BMS-650032) in humans. Xenobiotica. 2016;46(1):52-64.
5 Effect of CYP3A5*3 genetic variant on the metabolism of direct-acting antivirals in vitro: a different effect on asunaprevir versus daclatasvir and beclabuvir J Hum Genet. 2020 Jan;65(2):143-153. doi: 10.1038/s10038-019-0685-2.
6 DrugBank(Pharmacology-Metabolism)Asunaprevir

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