1755. Capravirine

Nomenclature

CAS number: 178979-85-6
5-[(3,5-Dichlorophenyl)thio]-4-(1-methylethyl)-1-(4-pyridinylmethyl)-1H-imidazole-2-methanol carbamate ester; 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole; AG-1549; S-1153.
C20H20Cl2N4O2S; mol wt 451.37.
C 53.22%, H 4.47%, Cl 15.71%, N 12.41%, O 7.09%, S 7.10%.

Description and references

Imidazole type non-nucleoside HIV-1 reverse transcriptase inhibitor (NNRTI). Prepn: H. Sugimoto, T. Fujiwara, WO 9610019; eidem, US 5910506 (1996, 1999 both to Shionogi). Antiviral activity: T. Fujiwara et al., Antimicrob. Agents Chemother. 42, 1340 (1998). Crystal structure in complex with target enzyme: J. Ren et al., J. Biol. Chem. 275, 14316 (2000). Review of pharmacology and clinical evaluation: W. M. Brown, Curr. Opin. Anti-Infect. Invest. Drugs 2, 286-294 (2000).

Chemical structure

Properties

Crystals from diethylether as hemihydrate, mp 88° (dec).

Therapeutic Category

Antiretroviral.

Keywords

Antiretroviral; Reverse Transcriptase Inhibitors; Nonnucleosides; Reverse Transcriptase Inhibitor