4250. Fosamprenavir

Nomenclature

CAS number: 226700-79-4
[(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)-2-(phosphonooxy)propyl]carbamic acid C-[(3S)-tetrahydro-3-furanyl] ester; (3S)-tetrahydro-3-furyl [(αS)-α-[(1R)-1-hydroxy-2-(N1-isobutylsulfanilamido)ethyl]phenethyl]carbamate dihydrogen phosphate (ester); VX-175.
C25H36N3O9PS; mol wt 585.61.
C 51.27%, H 6.20%, N 7.18%, O 24.59%, P 5.29%, S 5.48%.

Description and references

Peptidomimetic HIV protease inhibitor; water soluble prodrug of amprenavir, q.v. Prepn: R. D. Tung et al., WO 9933815; eidem, US 6559137 (1999, 2003 both to Vertex). Prepn of crystalline calcium salt: I. G. Armitage et al., WO 0004033 (2000 to Glaxo); eidem, US 6514953 (2003 to SKB). Clinical pharmacokinetics: C. Falcoz et al., J. Clin. Pharmacol. 42, 887 (2002). Review of pharmacology and clinical experience in HIV: T. M. Chapman et al., Drugs 64, 2101-2124 (2004); C. Arvieux, O. Tribut, ibid. 65, 633-659 (2005).

Chemical structure

Derivative

Calcium salt.

Nomenclature

CAS number: 226700-81-8
GW-433908G; Lexiva (GSK); Telzir (GSK).
C25H34CaN3O9PS; mol wt 623.67.
C 48.15%, H 5.49%, Ca 6.43%, N 6.74%, O 23.09%, P 4.97%, S 5.14%.

Properties

White microcrystalline needles, mp 282-284°. Soly in water (25°): 0.31 mg/ml.

Therapeutic Category

Antiretroviral.

Keywords

HIV Protease Inhibitor; Antiretroviral; Protease Inhibitors