Capravirine

Capravirine was a non-nucleoside reverse transcriptase inhibitor which reached phase II trials before development was discontinued by Pfizer.[1][2] Both phase IIb trials which were conducted failed to demonstrate that therapy with capravirine provided any significant advantage over existing triple-drug HIV therapies, and pharmacology studies showed that capravirine may interact with other HIV drugs.[3][4]

Capravirine

Names
IUPAC name [5-(3,5-Dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)imidazol-2-yl]methyl carbamate
Identifiers
CAS Number	178979-85-6^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL435128^N
ChemSpider	1717^N
PubChem CID	1783
UNII	VHC779598X^N
CompTox Dashboard (EPA)	DTXSID30170689
InChI 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)^N Key: YQXCVAGCMNFUMQ-UHFFFAOYSA-N^N InChI=1/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) Key: YQXCVAGCMNFUMQ-UHFFFAOYAP
SMILES O=C(OCc2nc(c(Sc1cc(Cl)cc(Cl)c1)n2Cc3ccncc3)C(C)C)N
Properties
Chemical formula	C20H20Cl2N4O2S
Molar mass	451.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References

1. PubChem. "Capravirine". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-06-02.
2. "Capravirine - Anti-Retroviral Drug". Drug Development Technology. Retrieved 2019-06-02.
3. "Capravirine - Anti-Retroviral Drug". Drug Development Technology. Retrieved 2019-06-02.
4. "A Study of Capravirine Plus VIRACEPT Plus Two Nucleoside Reverse Transcriptase Inhibitors in HIV-Infected Patients Who Failed Previous Anti-HIV Treatments - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2019-06-02.