DANOPREVIR

Possibly Marketed Outside US

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 Search

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
Sources: http://adisinsight.springer.com/drugs/800025457
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus serine protease, NS3/NS4A 12 Target ID: CHEMBL2095231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18824605	Inhibitor 7728		0.29 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 41 Sources: http://adisinsight.springer.com/drugs/800025457	Primary		Phase III 643	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
		252160348
Preclinical characteristics of the hepatitis C virus NS3/4A protease inhibitor ITMN-191 (R7227).	2008 Dec	18824605
Discovery of danoprevir (ITMN-191/R7227), a highly selective and potent inhibitor of hepatitis C virus (HCV) NS3/4A protease.	2014 Mar 13	23672640

Patents

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

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

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