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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

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

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

Unknown
149124
PubMed

PubMed

TitleDatePubMed
Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives.
2010-07
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.
2009-10-22
Pyrazole NNRTIs 4: selection of UK-453,061 (lersivirine) as a development candidate.
2009-10-15
Pyrazole NNRTIs 1: design and initial optimisation of a novel template.
2009-10-01
Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays.
2009-02-26
Optimization of 5-aryloxyimidazole non-nucleoside reverse transcriptase inhibitors.
2008-11
The use of local surface properties for molecular superimposition.
2008-09
Ritonavir 100 mg does not cause QTc prolongation in healthy subjects: a possible role as CYP3A inhibitor in thorough QTc studies.
2008-01
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.
2007-10
Evaluation of capravirine as a CYP3A probe substrate: in vitro and in vivo metabolism of capravirine in rats and dogs.
2007-09
Substrate-dependent inhibition or stimulation of HIV RNase H activity by non-nucleoside reverse transcriptase inhibitors (NNRTIs).
2007-01-12
A unique example of drug metabolism: tetra- and penta-oxygenation reactions of capravirine in rats, dogs and humans.
2007-01
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 2).
2006-12
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 1).
2006-12
Identification of enzymes responsible for primary and sequential oxygenation reactions of capravirine in human liver microsomes.
2006-11
In vitro selection of mutations in human immunodeficiency virus type 1 reverse transcriptase that confer resistance to capravirine, a novel nonnucleoside reverse transcriptase inhibitor.
2006-06
A concise and selective synthesis of novel 5-aryloxyimidazole NNRTIs.
2006-04-13
On the horizon: promising investigational antiretroviral agents.
2006
A lame duck, a dark horse, and a goat.
2005-10-01
A simple sequential incubation method for deconvoluting the complicated sequential metabolism of capravirine in humans.
2005-10
Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues.
2005-07-01
New targets and new drugs in the treatment of HIV.
2005-07
New drugs.
2005-07
Gateways to clinical trials.
2005-06
Emerging anti-HIV drugs.
2005-05
Capravirine, a nonnucleoside reverse-transcriptase inhibitor in patients infected with HIV-1: a phase 1 study.
2004-12-01
Gateways to clinical trials.
2004-10
New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections.
2004-10
Metabolism and excretion of capravirine, a new non-nucleoside reverse transcriptase inhibitor, alone and in combination with ritonavir in healthy volunteers.
2004-07
New antiretroviral agents for the treatment of HIV infection.
2004-06
Effect of stereo and regiochemistry towards wild and multidrug resistant HIV-1 virus: viral potency of chiral PETT derivatives.
2004-05-15
Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future.
2004-01
Susceptibility of feline immunodeficiency virus/human immunodeficiency virus type 1 reverse transcriptase chimeras to non-nucleoside RT inhibitors.
2004-01
Recent advances in the development of next generation non-nucleoside reverse transcriptase inhibitors.
2004
Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1.
2004
Gateways to clinical trials.
2003-11
Gateways to clinical trials.
2002-12
Highlights in the development of new antiviral agents.
2002-04
New developments in anti-HIV chemotherapy.
2001-11
Antiviral drugs: current state of the art.
2001-08
Capravirine trials stopped.
2001-04
New antiretroviral agents.
2001-03
Binding of the second generation non-nucleoside inhibitor S-1153 to HIV-1 reverse transcriptase involves extensive main chain hydrogen bonding.
2000-05-12
Structural determination of metabolites of S-1153, a new, potent, non-nucleoside, anti-HIV agent in rat liver microsomes.
1998-09
S-1153 inhibits replication of known drug-resistant strains of human immunodeficiency virus type 1.
1998-06
Patents

Patents

06054591
1
JP2009525265A
19
JP2009531441A
18

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
  • Download
Name Type Language
CAPRAVIRINE
INN   MI   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID30170689
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
PUBCHEM
1783
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
MERCK INDEX
m1053
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY Merck Index
FDA UNII
VHC779598X
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
CAS
178979-85-6
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
DRUG BANK
DB08502
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
NCI_THESAURUS
C81612
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
INN
7980
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
ChEMBL
CHEMBL435128
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
WIKIPEDIA
CAPRAVIRINE
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
USAN
KK-73
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
EVMPD
SUB20328
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
SMS_ID
100000078028
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
PRIMARY
Related Record Type Details
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1
TARGET ORGANISM->INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Structure of CAPRAVIRINE
EXCRETED UNCHANGED
Excretion of unchanged capravirine was negligible in urine.
URINE
Structure of CAPRAVIRINE
EXCRETED UNCHANGED
The amount of unchanged capravirine in feces was low ( 0.4% of the dose for group A and 1.4% of the dose for group B)
FECAL
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 POLYMERASE
TARGET -> INHIBITOR
Related Record Type Details
Structure of 5-((3,5-DICHLOROPHENYL)SULFINYL)-4-(1-METHYLETHYL)-1-(4-PYRIDINYLMETHYL)-1H-IMIDAZOLE-2-METHANOL 2-CARBAMATE
METABOLITE -> PARENT
FECAL; PLASMA; URINE
Structure of 1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)SULFINYL)-4-(1-METHYLETHYL)-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE
METABOLITE -> PARENT
URINE
Structure of 1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)SULFINYL)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-(4-PYRIDINYLMETHYL)-, 2-CARBAMATE
METABOLITE -> PARENT
FECAL; URINE
Structure of 2-(2-(((AMINOCARBONYL)OXY)METHYL)-5-((3,5-DICHLOROPHENYL)SULFINYL)-1-(4-PYRIDINYLMETHYL)-1H-IMIDAZOL-4-YL)-1,2-PROPANEDIOL
METABOLITE -> PARENT
FECAL
Structure of 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
FECAL; URINE
Structure of 1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)SULFONYL)-4-(1-METHYLETHYL)-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE
METABOLITE -> PARENT
URINE
Structure of 2-[[(Aminocarbonyl)oxy]methyl]-5-[(3,5-dichlorophenyl)thio]-?-methyl-1-(4-pyridinylmethyl)-1H-imidazole-4-ethanol
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of 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
URINE
Structure of 1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)THIO)-4-(1-METHYLETHYL)-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of 2-[[(Aminocarbonyl)oxy]methyl]-5-[(3,5-dichlorophenyl)thio]-?-methyl-1-(4-pyridinylmethyl)-1H-imidazole-4-ethanol
METABOLITE -> PARENT
FECAL; URINE
Structure of 1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)SULFONYL)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-(4-PYRIDINYLMETHYL)-, 2-CARBAMATE
METABOLITE -> PARENT
FECAL
Structure of 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
URINE
Structure of 5-((3,5-DICHLOROPHENYL)THIO)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-(4-PYRIDINYLMETHYL)-1H-IMIDAZOLE-2,4-DIMETHANOL 2-CARBAMATE
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of 1H-IMIDAZOLE-4-ACETIC ACID, 2-(((AMINOCARBONYL)OXY)METHYL)-5-((3,5-DICHLOROPHENYL)SULFONYL)-.ALPHA.-METHYL-1-(4-PYRIDINYLMETHYL)-
METABOLITE -> PARENT
FECAL
Structure of 1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)SULFONYL)-4-(1-METHYLETHYL)-1-(4-PYRIDINYLMETHYL)-, 2-CARBAMATE
METABOLITE -> PARENT
PLASMA; URINE
Related Record Type Details
Structure of CAPRAVIRINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC IN HEALTHY MALE VOLUNTEERS

SINGLE DOSE

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

IN HEALTHY MALE VOLUNTEERS

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