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

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
Capravirine trials stopped.	2001 Apr	11359665
Antiviral drugs: current state of the art.	2001 Aug	11418355
Highlights in the development of new antiviral agents.	2002 Apr	12370077
Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future.	2004 Jan	17191775
New antiretroviral agents for the treatment of HIV infection.	2004 Jun	16091227
Gateways to clinical trials.	2004 Oct	15605126
New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections.	2004 Oct	15351347
A lame duck, a dark horse, and a goat.	2005 May-Jun	16193576
A simple sequential incubation method for deconvoluting the complicated sequential metabolism of capravirine in humans.	2005 Oct	16006566
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 2).	2006 Dec	17089434
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 1).	2006 Dec	17089433
Identification of enzymes responsible for primary and sequential oxygenation reactions of capravirine in human liver microsomes.	2006 Nov	16914510
N2-benzyloxycarbonylguan-9-yl acetic acid derivatives as HIV-1 reverse transcriptase non-nucleoside inhibitors with decreased loss of potency against common drug-resistance mutations.	2007 Oct	17638375
Ritonavir 100 mg does not cause QTc prolongation in healthy subjects: a possible role as CYP3A inhibitor in thorough QTc studies.	2008 Jan	17581594
Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays.	2009 Feb 26	19175319
Pyrazole NNRTIs 1: design and initial optimisation of a novel template.	2009 Oct 1	19709880

Patents

Sample Use Guides

In Vivo Use Guide

1400 mg twice daily

Route of Administration: Oral

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