589. Amprenavir

Nomenclature

CAS number: 161814-49-9
N-[(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid (3S)-tetrahydro-3-furanyl ester; 4-amino-N-((2syn,3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzene sulfonamide; 141W94; KVX-478; VX-478; Agenerase (GSK); Prozei (Kissei).
C25H35N3O6S; mol wt 505.63.
C 59.38%, H 6.98%, N 8.31%, O 18.99%, S 6.34%.

Description and references

Peptidomimetic HIV protease inhibitor. Prepn: R. D. Tung et al., WO 9405639; eidem, US 5585397 (1994, 1996 both to Vertex). Crystal structure of complex with HIV protease: E. E. Kim et al., J. Am. Chem. Soc. 117, 1181 (1995). Review of design strategy: M. A. Navia et al., Int. Antiviral News 3, 143-145 (1995); of pharmacology and clinical evaluation: J. C. Adkins, D. Faulds, Drugs 55, 837-842 (1998).

Chemical structure

Properties

White to cream-colored solid. Soly in water (25°): 0.04 mg/ml.

Therapeutic Category

Antiretroviral.

Keywords

HIV Protease Inhibitor; Antiretroviral; Protease Inhibitors