6443. Nelfinavir

Nomenclature

CAS number: 159989-64-7
(3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide; [3S-(3R*,4aR*,8aR*,2′S*,3′S*)]-2-[2′-hydroxy-3′-phenylthiomethyl-4′-aza-5′-oxo-5′-(2″-methyl-3″-hydroxyphenyl)pentyl]decahydroisoquinoline-3-N-t-butylcarboxamide; AG-1346.
C32H45N3O4S; mol wt 567.78.
C 67.69%, H 7.99%, N 7.40%, O 11.27%, S 5.65%.

Description and references

Peptidomimetic HIV protease inhibitor. Prepn: B. A. Dressman et al., WO 9509843; eidem, US 5484926 (1995, 1996 both to Agouron). Physical properties: M. Longer et al., J. Pharm. Sci. 84, 1090 (1995). HIV protease inhibition and antiviral activity: A. K. Patick et al., Antimicrob. Agents Chemother. 40, 292 (1996). Preclinical pharmacokinetics and tissue distribution: B. V. Shetty et al., ibid. 110. Review of pharmacology and clinical efficacy in HIV infection: A. Bardsley-Elliot, G. L. Plosker et al., Drugs 59, 581-620 (2000); of clinical experience: M. Olmo, D. Podzamczer, Expert Opin. Drug Metab. Toxicol. 2, 285-300 (2006).

Chemical structure

Properties

White foam. [α]D -119.23° (c = 0.26 in methanol). pKa1 6.0; pKa2 11.06. Log P (octanol/water): 4.1. Practically insol in water.

Derivative

Methanesulfonate.

Nomenclature

CAS number: 159989-65-8
Nelfinavir mesylate; AG-1343; Viracept (Agouron).
C32H45N3O4S.CH3SO3H; mol wt 663.89.
C 59.70%, H 7.44%, N 6.33%, O 16.87%, S 9.66%.

Properties

White powder. pKa -1.20. Soly (mg/ml): 4.5 in water; 2.6 in 0.1N HCl. Soly (mg/g): 70 in glycerin; >100 in propylene glycol; >200 in PEG 400. Very sol in methanol, ethanol, acetonitrile. Practically insol in soybean oil, mineral oil.

Therapeutic Category

Antiretroviral.

Keywords

HIV Protease Inhibitor; Antiretroviral; Protease Inhibitors