866. Atovaquone

Nomenclature

CAS number: 95233-18-4
2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione; trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; 566C80; BW-566C; BW-566C-80; Mepron (GSK); Wellvone (GSK).
C22H19ClO3; mol wt 366.84.
C 72.03%, H 5.22%, Cl 9.66%, O 13.08%.

Description and references

Hydroxynaphthoquinone derivative that inhibits mitochondrial electron transport. Prepn: A. T. Hudson, A. W. Randall, EP 123238; eidem, US 5053432 (1984, 1991 both to Burroughs Wellcome). Antiprotozoal activity, metabolism, and pharmacokinetics: A. T. Hudson et al., Drugs Exp. Clin. Res. 17, 427 (1991). Mechanism of action study: M. Fry, M. Pudney, Biochem. Pharmacol. 43, 1545 (1992). Clinical trial for prevention of pneumocystis pneumonia in AIDS patients: W. M. El-Sadr et al., N. Engl. J. Med. 339, 1889 (1998).

Chemical structure

Properties

Crystals from acetonitrile, mp 216-219°. Practically insol in water.

Therapeutic Category

Antipneumocystic.

Keywords

Antipneumocystic