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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H46FN5O9S
Molecular Weight 731.831
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DANOPREVIR

SMILES

[H][C@@]12C[C@H](CN1C(=O)[C@H](CCCCCC=C[C@@H]3C[C@]3(NC2=O)C(=O)NS(=O)(=O)C4CC4)NC(=O)OC(C)(C)C)OC(=O)N5CC6=C(C5)C(F)=CC=C6

InChI

InChIKey=ZVTDLPBHTSMEJZ-JSZLBQEHSA-N
InChI=1S/C35H46FN5O9S/c1-34(2,3)50-32(45)37-27-13-8-6-4-5-7-11-22-17-35(22,31(44)39-51(47,48)24-14-15-24)38-29(42)28-16-23(19-41(28)30(27)43)49-33(46)40-18-21-10-9-12-26(36)25(21)20-40/h7,9-12,22-24,27-28H,4-6,8,13-20H2,1-3H3,(H,37,45)(H,38,42)(H,39,44)/b11-7-/t22-,23-,27+,28+,35-/m1/s1

HIDE SMILES / InChI

Description

Danoprevir (ITMN-191, RG7227) is a peptidomimetic inhibitor of the NS3/4A protease of HCV. The second-generation, direct acting antiviral agent was originated by Array BioPharma and InterMune (a subsidiary of Roche), and then sold to Roche. Danoprevir has demonstrated potency against mutant HCV strains. Phase III development is underway for HCV infections in China, and phase II development for the same indication is underway in the US, Australia, Brazil, Canada, Mexico, New Zealand, Puerto Rico, Taiwan and certain European countries.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.29 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
In a Phase I study, danoprevir monotherapy was administered for 14 days in ascending doses ranging from 200 to 600 mg per day: The antiviral effectiveness increased in a dose-dependent manner, with a 14-day time-averaged effectiveness of 0.95 at the lowest dose (100 mg twice daily) and 0.99 at the highest dose (200 mg three times daily).
Route of Administration: Other
In Vitro Use Guide
Dose-dependent reductions of a patient-derived HCV genotype 1b replicon harbored in hepatocyte-derived Huh7 cells were observed following 2-day incubation with danoprevir (ITMN-191, RG7227): EC50 is 1.8 nM