CAPRAVIRINE

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

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 of CAPRAVIRINE

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

PubMed

Title	Date	PubMed
Highlights in the development of new antiviral agents.	2002 Apr	12370077
Gateways to clinical trials.	2002 Dec	12616965
Gateways to clinical trials.	2003 Nov	14685303
Recent advances in the development of next generation non-nucleoside reverse transcriptase inhibitors.	2004	15193138
Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1.	2004	15134549
Capravirine, a nonnucleoside reverse-transcriptase inhibitor in patients infected with HIV-1: a phase 1 study.	2004 Dec 1	15529260
New drugs.	2005 Jul	16011526
Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues.	2005 Jul 1	15896963
Gateways to clinical trials.	2005 Jun	16082422
Emerging anti-HIV drugs.	2005 May	15934866
A simple sequential incubation method for deconvoluting the complicated sequential metabolism of capravirine in humans.	2005 Oct	16006566
On the horizon: promising investigational antiretroviral agents.	2006	16515488
Ritonavir 100 mg does not cause QTc prolongation in healthy subjects: a possible role as CYP3A inhibitor in thorough QTc studies.	2008 Jan	17581594
Optimization of 5-aryloxyimidazole non-nucleoside reverse transcriptase inhibitors.	2008 Nov	18855969
The use of local surface properties for molecular superimposition.	2008 Sep	18500543

Patents

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

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

Code System Code Type Description

EPA CompTox

DTXSID30170689

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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PUBCHEM

1783

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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MERCK INDEX

m1053

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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Merck Index

FDA UNII

VHC779598X

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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CAS

178979-85-6

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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DRUG BANK

DB08502

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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NCI_THESAURUS

C81612

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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INN

7980

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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ChEMBL

CHEMBL435128

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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WIKIPEDIA

CAPRAVIRINE

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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USAN

KK-73

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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EVMPD

SUB20328

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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SMS_ID

100000078028

Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023

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ACTIVE MOIETY


					VHC779598X

METABOLITE (PARENT)


					7U2NH9TAP8

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

METABOLITE (PARENT)


					C06YW91KZ5

1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)SULFINYL)-4-(1-METHYLETHYL)-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE

METABOLITE (PARENT)


					E3CEZ64VR2

1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)SULFINYL)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-(4-PYRIDINYLMETHYL)-, 2-CARBAMATE

METABOLITE (PARENT)


					WA2E3EQT7T

2-(2-(((AMINOCARBONYL)OXY)METHYL)-5-((3,5-DICHLOROPHENYL)SULFINYL)-1-(4-PYRIDINYLMETHYL)-1H-IMIDAZOL-4-YL)-1,2-PROPANEDIOL

METABOLITE (PARENT)


					EKR5H9BQ5Q

1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)THIO)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, .ALPHA.2-CARBAMATE

METABOLITE (PARENT)


					FDD8M74ZV4

1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)SULFONYL)-4-(1-METHYLETHYL)-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE

METABOLITE (PARENT)


					GDQ25AQ7KH

1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)SULFONYL)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE

METABOLITE (PARENT)


					E5DZR74FBN

1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)THIO)-4-(1-METHYLETHYL)-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE

METABOLITE (PARENT)


					8WK6EAJ7U2

1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)SULFONYL)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-(4-PYRIDINYLMETHYL)-, 2-CARBAMATE

METABOLITE (PARENT)


					BV53MR8T4W

1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)SULFINYL)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE

METABOLITE (PARENT)


					ECG1QCI7DB

5-((3,5-DICHLOROPHENYL)THIO)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-(4-PYRIDINYLMETHYL)-1H-IMIDAZOLE-2,4-DIMETHANOL 2-CARBAMATE

METABOLITE (PARENT)


					BZ45AR2SES

1H-IMIDAZOLE-4-ACETIC ACID, 2-(((AMINOCARBONYL)OXY)METHYL)-5-((3,5-DICHLOROPHENYL)SULFONYL)-.ALPHA.-METHYL-1-(4-PYRIDINYLMETHYL)-

METABOLITE (PARENT)


					FE3XQ66QCX

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