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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H46FN5O9S
Molecular Weight 731.8337
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DANOPREVIR

SMILES

CC(C)(C)OC(=N[C@@]1([H])CCCCC/C(/[H])=C(/[H])\[C@]2([H])C[C@@]2(C(=NS(=O)(=O)C3CC3)O)N=C([C@]4([H])C[C@]([H])(CN4C1=O)OC(=O)N5Cc6cccc(c6C5)F)O)O

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

Molecular Formula C35H46FN5O9S
Molecular Weight 731.8337
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18824605

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.29 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Preclinical characteristics of the hepatitis C virus NS3/4A protease inhibitor ITMN-191 (R7227).
2008 Dec
Discovery of danoprevir (ITMN-191/R7227), a highly selective and potent inhibitor of hepatitis C virus (HCV) NS3/4A protease.
2014 Mar 13
Patents

Sample Use Guides

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
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:27:21 UTC 2021
Edited
by admin
on Fri Jun 25 22:27:21 UTC 2021
Record UNII
911Z9PCQ5F
Record Status Validated (UNII)
Record Version
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Name Type Language
DANOPREVIR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
R05190591
Code English
DANOPREVIR [WHO-DD]
Common Name English
DANOPREVIR [USAN]
Common Name English
R-05190591
Code English
RO-5190591
Code English
DANOPREVIR [INN]
Common Name English
RO5190591
Code English
Code System Code Type Description
EVMPD
SUB33614
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
NCI_THESAURUS
C171872
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
INN
9209
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
MESH
C553752
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
PUBCHEM
11285588
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
DRUG BANK
DB11779
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
CAS
850876-88-9
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL2311191
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
FDA UNII
911Z9PCQ5F
Created by admin on Fri Jun 25 22:27:21 UTC 2021 , Edited by admin on Fri Jun 25 22:27:21 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY