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

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

Approval Year

Unknown
86413
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
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 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 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

NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966