3521. Efavirenz

Nomenclature

CAS number: 154598-52-4
(4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; DMP-266; Stocrin (Merck & Co.); Sustiva (BMS).
C14H9ClF3NO2; mol wt 315.67.
C 53.27%, H 2.87%, Cl 11.23%, F 18.06%, N 4.44%, O 10.14%.

Description and references

Nonnucleoside reverse transcriptase inhibitor (NNRTI). Prepn: S. D. Young et al., EP 582455; eidem, US 5519021 (1994, 1996 both to Merck & Co.). Pharmacology: S. D. Young et al., Antimicrob. Agents Chemother. 39, 2602 (1995). Enantioselective synthesis: A. S. Thompson et al., Tetrahedron Lett. 36, 8937 (1995). Total synthesis and resolution of enantiomers: L. A. Radesca et al., Synth. Commun. 27, 4373 (1997). Ionization behavior: S. R. Rabel et al., Pharm. Dev. Technol. 1, 91 (1996). Clinical trial as component of combination therapy in HIV-1 infection in adults: S. Staszewski et al., N. Engl. J. Med. 341, 1865 (1999); in children: S. E. Starr et al., ibid. 1874. Review of clinical experience: C. Fortin, V. Joly, Expert Rev. Anti Infect. Ther. 2, 671-684 (2004).

Chemical structure

Properties

Crystals from toluene:heptane, mp 139-141°. [α]D20 -84.7° (c = 0.005 g/ml in CH3Cl). [α]D25 -94.1° (c = 0.300 in methanol). pKa 10.2.

Therapeutic Category

Antiretroviral.

Keywords

Reverse Transcriptase Inhibitor; Antiretroviral; Reverse Transcriptase Inhibitors; Nonnucleosides