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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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
S-1153 inhibits replication of known drug-resistant strains of human immunodeficiency virus type 1.
1998 Jun
Structural determination of metabolites of S-1153, a new, potent, non-nucleoside, anti-HIV agent in rat liver microsomes.
1998 Sep
Capravirine trials stopped.
2001 Apr
Antiviral drugs: current state of the art.
2001 Aug
Highlights in the development of new antiviral agents.
2002 Apr
Gateways to clinical trials.
2002 Dec
Gateways to clinical trials.
2003 Nov
Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1.
2004
Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future.
2004 Jan
Metabolism and excretion of capravirine, a new non-nucleoside reverse transcriptase inhibitor, alone and in combination with ritonavir in healthy volunteers.
2004 Jul
New antiretroviral agents for the treatment of HIV infection.
2004 Jun
New targets and new drugs in the treatment of HIV.
2005 Jul
New drugs.
2005 Jul
Gateways to clinical trials.
2005 Jun
Emerging anti-HIV drugs.
2005 May
A lame duck, a dark horse, and a goat.
2005 May-Jun
A simple sequential incubation method for deconvoluting the complicated sequential metabolism of capravirine in humans.
2005 Oct
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 2).
2006 Dec
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 1).
2006 Dec
Identification of enzymes responsible for primary and sequential oxygenation reactions of capravirine in human liver microsomes.
2006 Nov
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
Evaluation of capravirine as a CYP3A probe substrate: in vitro and in vivo metabolism of capravirine in rats and dogs.
2007 Sep
Ritonavir 100 mg does not cause QTc prolongation in healthy subjects: a possible role as CYP3A inhibitor in thorough QTc studies.
2008 Jan
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
Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives.
2010 Jul
Patents

Sample Use Guides

1400 mg twice daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:43 UTC 2023
Edited
by admin
on Fri Dec 15 16:13:43 UTC 2023
Record UNII
VHC779598X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAPRAVIRINE
INN   MI   USAN   WHO-DD  
USAN   INN  
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 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID30170689
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
PUBCHEM
1783
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
MERCK INDEX
m1053
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY Merck Index
FDA UNII
VHC779598X
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
CAS
178979-85-6
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
DRUG BANK
DB08502
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
NCI_THESAURUS
C81612
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
INN
7980
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL435128
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
WIKIPEDIA
CAPRAVIRINE
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
USAN
KK-73
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
EVMPD
SUB20328
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
SMS_ID
100000078028
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
EXCRETED UNCHANGED
Excretion of unchanged capravirine was negligible in urine.
URINE
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
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
FECAL; PLASMA; URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
FECAL; URINE
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
FECAL; URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
PLASMA; URINE
Related Record Type Details
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