Nelfinavir
Title: Nelfinavir
CAS Registry Number: 159989-64-7
CAS Name: (3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide
Additional Names: [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
Manufacturers' Codes: AG-1346
Molecular Formula: C32H45N3O4S
Molecular Weight: 567.78
Percent Composition: C 67.69%, H 7.99%, N 7.40%, O 11.27%, S 5.65%
Literature References: 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).
Properties: White foam. [a]D -119.23° (c = 0.26 in methanol). pKa1 6.0; pKa2 11.06. Log P (octanol/water): 4.1. Practically insol in water.
pKa: pKa1 6.0; pKa2 11.06
Optical Rotation: [a]D -119.23° (c = 0.26 in methanol)
Log P: Log P (octanol/water): 4.1
 
Derivative Type: Methanesulfonate
CAS Registry Number: 159989-65-8
Additional Names: Nelfinavir mesylate
Manufacturers' Codes: AG-1343
Trademarks: Viracept (Agouron)
Molecular Formula: C32H45N3O4S.CH3SO3H
Molecular Weight: 663.89
Percent Composition: 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.
pKa: pKa -1.20
 
Therap-Cat: Antiviral.
Keywords: Antiviral; Peptidomimetics; HIV Protease Inhibitor.

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