CAPRAVIRINE

Investigational

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
Structural determination of metabolites of S-1153, a new, potent, non-nucleoside, anti-HIV agent in rat liver microsomes.	1998 Sep	9764929
Binding of the second generation non-nucleoside inhibitor S-1153 to HIV-1 reverse transcriptase involves extensive main chain hydrogen bonding.	2000 May 12	10799511
Antiviral drugs: current state of the art.	2001 Aug	11418355
New antiretroviral agents.	2001 Mar	12184261
Gateways to clinical trials.	2002 Dec	12616965
Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1.	2004	15134549
Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future.	2004 Jan	17191775
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
Substrate-dependent inhibition or stimulation of HIV RNase H activity by non-nucleoside reverse transcriptase inhibitors (NNRTIs).	2007 Jan 12	17113568
Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays.	2009 Feb 26	19175319
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

Patents

Sample Use Guides

In Vivo Use Guide

1400 mg twice daily

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:29 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:29 GMT 2025`
Record UNII	VHC779598X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAPRAVIRINE

Official Name

English

CAPRAVIRINE [MI]

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C97453