ASUNAPREVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H46ClN5O9S
Molecular Weight	748.286
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CN=C(O[C@@H]2C[C@H](N(C2)C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)N[C@@]3(C[C@H]3C=C)C(=O)NS(=O)(=O)C4CC4)C5=C1C=CC(Cl)=C5

InChI

InChIKey=XRWSZZJLZRKHHD-WVWIJVSJSA-N

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

HIDE SMILES / InChI

Molecular Formula	C35H46ClN5O9S
Molecular Weight	748.286
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.guildlink.com.au/gc/ws/bms/pi.cfm?product=bqpsunve10715
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25117197 | https://news.bms.com/press-release/japan-approves-first-all-oral-interferon-and-ribavirin-free-hepatitis-c-treatment-dakl | https://www.tga.gov.au/auspar/auspar-asunaprevir | http://www.hepctip.ca/drug-pipeline-2/sunvepra-asunaprevir-canada/

Asunaprevir is a direct acting antiviral agent (DAA) against the hepatitis C virus Asunaprevir is an inhibitor of the HCV NS3/4A serine protease complex. This NS3/4A enzyme complex is responsible for processing the HCV polyprotein to yield mature viral proteins required for viral replication. The combination of daclatasvir + asunaprevir [Daklinza(®) + Sunvepra(®)], two direct-acting antiviral agents, has been developed by Bristol-Myers Squibb for the treatment of patients with chronic hepatitis C virus (HCV) genotype 1 infections, including those with compensated cirrhosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Hepatitis C virus serine protease, NS3/NS4A 13 Target ID: CHEMBL2095231 Sources: http://www.guildlink.com.au/gc/ws/bms/pi.cfm?product=bqpsunve10715	Inhibitor 8297	0.3 nM [IC50]
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25670521	Inhibitor 8297	0.3 µM [IC50]
Solute carrier organic anion transporter family member 2B1 2 Target ID: CHEMBL1743124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25670521	Inhibitor 8297	0.27 µM [IC50]
Solute carrier organic anion transporter family member 1B3 16 Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25670521	Inhibitor 8297	3.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25117197	Primary		Approved 8429	SUNVEPRA Approved Use SUNVEPRA (asunaprevir) is indicated in combination with other medicinal products for the treatment of chronic hepatitis C virus (HCV) infection in adults with compensated liver disease (including cirrhosis)

PubMed

Title	Date	PubMed
Combinations of lambda interferon with direct-acting antiviral agents are highly efficient in suppressing hepatitis C virus replication.	2013 Mar	23274666
Combination treatment with hepatitis C virus protease and NS5A inhibitors is effective against recombinant genotype 1a, 2a, and 3a viruses.	2013 Mar	23274664
Highly efficient infectious cell culture of three hepatitis C virus genotype 2b strains and sensitivity to lead protease, nonstructural protein 5A, and polymerase inhibitors.	2014 Feb	23913364
The discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection.	2014 Mar 13	24564672

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose of SUNVEPRA (asunaprevir) is 100 mg twice daily. SUNVEPRA must be administered in combination with DAKLINZA or with DAKLINZA, peginterferon alfa, and ribavirin.

Route of Administration: Oral

In Vitro Use Guide

In cell-based HCV replicon assays, asunaprevir inhibited HCV genotypes 1a(H77 strain) and, 1b(Con1 strain) with effective concentration (50% reduction, EC50) values of 4 nM and 1.2 nM, , respectively. The EC50 values against a genotype 2a replicon and hybrid replicons encoding the NS3 protease domain representing HCV genotypes 2b and 3a were 230 nM, 480 nM, and 1162 nM, respectively. Against hybrid replicons encoding the NS3 protease domain representing HCV genotype 4a, observed EC50 values ranged from 1.8 nM to 7.6 nM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 22:10:28 GMT 2023` Edited by `admin` on `Fri Dec 15 22:10:28 GMT 2023`
Record UNII	S9X0KRJ00S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ASUNAPREVIR

Official Name

English

ASUNAPREVIR [JAN]

Common Name

English

BMS650032

Code

English

ASUNAPREVIR [MI]

Common Name

English

Asunaprevir [WHO-DD]

Common Name

English

BMS-650032

Code

English

ASUNAPREVIR [USAN]

Common Name

English

SUNVEPRA

Brand Name

English

TERT-BUTYL ((2S)-1-((2S,4R)-4-((7-CHLORO-4-METHOXYISOQUINOLIN-1-YL)OXY)-2-(((1R,2S)-1-((CYCLOPROPANESULFONYL)CARBAMOYL)-2-ETHENYLCYCLOPROPYL)CARBAMOYL)PYRROLIDIN-1-YL)-3,3-DIMETHYL-1-OXOBUTAN-2-YL)CARBAMATE

Common Name

English

asunaprevir [INN]

Common Name

English

CYCLOPROPANECARBOXAMIDE, N-((1,1-DIMETHYLETHOXY)CARBONYL)-3-METHYL-L-VALYL-(4R)-4-((7-CHLORO-4-METHOXY-1-ISOQUINOLINYL)OXY)-L-PROLYL-1-AMINO-N-(CYCLOPROPYLSULFONYL)-2-ETHENYL-, (1R,2S)-

Common Name

English

ASV

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C783