Capravirine

HCID 1783

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Basic information

CAS: 178979-85-6
Standard SMILES: CC(C)c1nc(COC(N)=O)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1
InChIKey: YQXCVAGCMNFUMQ-UHFFFAOYSA-N
Molecular formula: C20H20Cl2N4O2S
Average molar mass: 451.4 g/mol
Monoisotopic mass: 450.06840224

Overview

Capravirine is a non-nucleoside reverse transcriptase inhibitor. Capravirine shows antiviral activity against wild-type HIV as well as HIV strains with mutations in reverse transcriptase. Due to no statistically-significant difference between standard triple-drug HIV therapies and the same therapy with capravirine, its development was discontinued by the developer.

Names & identifiers

Preferred name: Capravirine
IUPAC: [5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)imidazol-2-yl]methyl carbamate
English name: Capravirine
Molecular formula: C20H20Cl2N4O2S
Molecular weight: 451.37

Names & synonyms

Capravirine178979-85-6S-1153CapravirinaVHC779598XAG 549AG1549S 1153DTXSID301706891H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-, carbamate (ester)5-((3,5-Dichlorophenyl)thio)-4-isopropyl-1-(4-pyridylmethyl)imidazole-2-methanol carbamate (ester)capravirinum

Show more names

CdimiAGI 549Aids058025Aids-058025Capravirine D6YQXCVAGCMNFUMQ-UHFFFAOYSA-N5-(3,5-Dichlorophenyl)thio-4-isopropyl-1-(4-pyridyl)methyl-1H-imidazol-2-ylmethyl carbamate1H-Imidazole-2-methanol, 5-[(3,5-dichlorophenyl)thio]-4-(1-methylethyl)-1-(4-pyridinylmethyl)-, 2-carbamate

(5-((3,5-dichlorophenyl)sulfanyl)-4-(propan-2-yl)-1-(pyridin-4-ylmethyl)-1H-imidazol-2-yl)methyl carbamate{5-[(3,5-dichlorophenyl)sulfanyl]-4-(propan-2-yl)-1-(pyridin-4-ylmethyl)-1H-imidazol-2-yl}methyl carbamate5-[(3,5-Dichlorophenyl)thio]-4-isopropyl-1-(4-pyridylmethyl)imidazole-2-methanol carbamate (ester)RefChem:573747DTXCID0093180(5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)imidazol-2-yl)methyl aminoformateS1153AG 1549

Database identifiers

CAS: 178979-85-6
PubChem CID: 1783
DTXSID: DTXSID30170689
ChEMBL: CHEMBL435128
UNII: VHC779598X
Nikkaji: J956.384I

Properties

Computed structural properties

XLogP: 4.5
Topological polar surface area: 108 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 8
Heavy atoms: 29
Formal charge: 0
Complexity: 529

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point: 88 ° · 88° (dec)
Boiling point: 646 · 646.0±55.0 °C(Predicted)
Density: 1.4 · 1.40±0.1 g/cm3(Predicted)
pka: 13.01 · 13.01±0.50(Predicted)
FDA UNII: 779598 X · VHC779598X

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template.

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS.