Details of the Drug

General Information of Drug (ID: DMQI43G)

Drug Name
BMS 650032
Synonyms
Asunaprevir; 630420-16-5; BMS-650032; UNII-S9X0KRJ00S; BMS 650032; S9X0KRJ00S; Asunaprevir (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; Asunaprevir [USAN:INN]; Sunvepra (TN); 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; 2R9
Indication
Disease Entry ICD 11 Status REF
Hepatitis C virus infection 1E51.1 Phase 2 [1]
Affected Organisms
Hepatitis C Virus
ATC Code
J05AP06: BMS 650032
J05AP: Antivirals for treatment of HCV infections
J05A: DIRECT ACTING ANTIVIRALS
J05: ANTIVIRALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 748.3
Logarithm of the Partition Coefficient (xlogp) 4.9
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 10
ADMET Property
Bioavailability
The bioavailability of drug is 70% [2]
Clearance
The apparent oral clearance of drug is 302-491 L/h [3]
Elimination
From the administered dose, 84% is excreted by feces mainly as metabolites and less than 1% of the dose is recovered as metabolites in the urine [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 15 - 20 hours [3]
Metabolism
The drug is metabolized via the liver [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.012% [4]
Vd
The volume of distribution (Vd) of drug is 194 L [5]
Chemical Identifiers
Formula
C35H46ClN5O9S
IUPAC Name
tert-butyl N-[(2S)-1-[(2S,4R)-4-(7-chloro-4-methoxyisoquinolin-1-yl)oxy-2-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
Canonical SMILES
CC(C)(C)[C@@H](C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@@]2(C[C@H]2C=C)C(=O)NS(=O)(=O)C3CC3)OC4=NC=C(C5=C4C=C(C=C5)Cl)OC)NC(=O)OC(C)(C)C
InChI
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
Cross-matching ID
PubChem CID
16076883
ChEBI ID
CHEMBL134723
CAS Number
630420-16-5
UNII
S9X0KRJ00S
DrugBank ID
DB11586
TTD ID
D04MCY
VARIDT ID
DR00075
INTEDE ID
DR0148
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Protease (HIV PR) TT5FNQT POL_HV1B1 Inhibitor [1]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [8]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [9]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [9]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [9]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [7]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 2011 Pipeline of Bristol-Myers Squibb.
2 FDA Approved Drug Products: Risperdal (risperidone) for oral use
3 Asunaprevir, a protease inhibitor for the treatment of hepatitis C infection. Ther Clin Risk Manag. 2014 Jun 26;10:493-504. doi: 10.2147/TCRM.S66731. eCollection 2014.
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir
6 KEGG: new perspectives on genomes, pathways, diseases and drugs. Nucleic Acids Res. 2017 Jan 4;45(D1):D353-D361. (dg:DG01665)
7 Characterization of ADME properties of [(14)C]asunaprevir (BMS-650032) in humans. Xenobiotica. 2016;46(1):52-64.
8 Asunaprevir: a review of preclinical and clinical pharmacokinetics and drug-drug interactions. Clin Pharmacokinet. 2015 Dec;54(12):1205-22.
9 Australian Public Assessment Report for asunaprevir.