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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 of ASUNAPREVIR

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.3 nM [IC50]
0.3 µM [IC50]
0.27 µM [IC50]
3.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SUNVEPRA

PubMed

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
Record UNII
S9X0KRJ00S
Record Status Validated (UNII)
Record Version