DANOPREVIR SODIUM

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H45FN5O9S.Na
Molecular Weight	753.813
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[H][C@@]12C[C@H](CN1C(=O)[C@H](CCCCCC=C[C@@H]3C[C@]3(NC2=O)C(=O)[N-]S(=O)(=O)C4CC4)NC(=O)OC(C)(C)C)OC(=O)N5CC6=C(C5)C(F)=CC=C6

InChI

InChIKey=GXYYUDQAGCVAGJ-HHGSPMIASA-M

InChI=1S/C35H46FN5O9S.Na/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,(H3,37,38,39,42,44,45);/q;+1/p-1/b11-7-;/t22-,23-,27+,28+,35-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C35H46FN5O9S
Molecular Weight	731.831
Charge	0
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 13 Target ID: CHEMBL2095231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18824605	Inhibitor 8297		0.29 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 42 Sources: http://adisinsight.springer.com/drugs/800025457	Primary		Phase III 656	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 Dec 15 19:50:44 GMT 2023` Edited by `admin` on `Fri Dec 15 19:50:44 GMT 2023`
Record UNII	217RJI972K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DANOPREVIR SODIUM

Official Name

English

DANOPREVIR SODIUM [USAN]

Common Name

English

Danoprevir sodium [WHO-DD]

Common Name

English

R7227

Code

English

R-7227

Code

English

RO-5190591-001

Code

English

RO5190591-001

Code

English

ITMN-191

Code

English

Code System Code Type Description

PUBCHEM

23718928