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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:134723
CAS Number: 630420-16-5
DrugBank ID: DB11586
TTD ID: D04MCY
VARIDT ID: DR00075
INTEDE ID: DR0148

Combinatorial Drugs (CBD)

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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]

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Drug Transporter (DTP)

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

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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.