CAPRAVIRINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H20Cl2N4O2S
Molecular Weight	451.369
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=C(SC2=CC(Cl)=CC(Cl)=C2)N(CC3=CC=NC=C3)C(COC(N)=O)=N1

InChI

InChIKey=YQXCVAGCMNFUMQ-UHFFFAOYSA-N

InChI=1S/C20H20Cl2N4O2S/c1-12(2)18-19(29-16-8-14(21)7-15(22)9-16)26(10-13-3-5-24-6-4-13)17(25-18)11-28-20(23)27/h3-9,12H,10-11H2,1-2H3,(H2,23,27)

HIDE SMILES / InChI

Molecular Formula	C20H20Cl2N4O2S
Molecular Weight	451.369
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22934811 | https://www.ncbi.nlm.nih.gov/pubmed/19356020 | https://www.ncbi.nlm.nih.gov/pubmed/15205383 | https://www.ncbi.nlm.nih.gov/pubmed/16914510

Capravirine (S-1153, AG1549) is a 1,2,4,5-tetrasubstituted imidazole derivative patented by pharmaceutical company Shionogi as specific inhibitors of HIV-1 reverse transcriptase. However, safety and efficacy studies showed that Capravirine had no specific advantages over currently used NNRTIs. Consequently, clinical trials were discontinued after phase IIb.

Originator

Approval Year

PubMed

Title	Date	PubMed
S-1153 inhibits replication of known drug-resistant strains of human immunodeficiency virus type 1.	1998 Jun	9624472
Gateways to clinical trials.	2002 Dec	12616965
Emerging anti-HIV drugs.	2005 May	15934866
On the horizon: promising investigational antiretroviral agents.	2006	16515488
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 1).	2006 Dec	17089433
In vitro selection of mutations in human immunodeficiency virus type 1 reverse transcriptase that confer resistance to capravirine, a novel nonnucleoside reverse transcriptase inhibitor.	2006 Jun	16472877
Identification of enzymes responsible for primary and sequential oxygenation reactions of capravirine in human liver microsomes.	2006 Nov	16914510
Pyrazole NNRTIs 1: design and initial optimisation of a novel template.	2009 Oct 1	19709880
Pyrazole NNRTIs 4: selection of UK-453,061 (lersivirine) as a development candidate.	2009 Oct 15	19748778
Conformational landscape of the human immunodeficiency virus type 1 reverse transcriptase non-nucleoside inhibitor binding pocket: lessons for inhibitor design from a cluster analysis of many crystal structures.	2009 Oct 22	19827836
Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives.	2010 Jul	20379971

Patents

Sample Use Guides

In Vivo Use Guide

1400 mg twice daily

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:13:43 GMT 2023` Edited by `admin` on `Fri Dec 15 16:13:43 GMT 2023`
Record UNII	VHC779598X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAPRAVIRINE

Official Name

English

1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)THIO)-4-(1-METHYLETHYL)-1-(4-PYRIDINYLMETHYL)-, CARBAMATE (ESTER)

Common Name

English

CAPRAVIRINE [USAN]

Common Name

English

capravirine [INN]

Common Name

English

S-1153

Code

English

5-[(3,5-Dichlorophenyl)thio]-4-isopropyl-1-(4-pyridylmethyl)imidazole-2-methanol carbamate (ester)

Common Name

English

Capravirine [WHO-DD]

Common Name

English

CAPRAVIRINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97453