Atazanavir
Title: Atazanavir
CAS Registry Number: 198904-31-3
CAS Name: (3S,8S,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-2,5,6,10,13-pentaazatetradecanedioic acid dimethyl ester
Additional Names: 1-[4-(pyridin-2-yl)phenyl]-5S-2,5-bis[[N-(methoxycarbonyl)-L-tert-leucinyl]amino]-4S-hydroxy-6-phenyl-2-azahexane
Manufacturers' Codes: BMS-232632; CGP-73547
Molecular Formula: C38H52N6O7
Molecular Weight: 704.86
Percent Composition: C 64.75%, H 7.44%, N 11.92%, O 15.89%
Literature References: Azapeptide HIV protease inhibitor. Prepn: A. Fässler et al., WO 9740029; eidem, US 5849911 (1997, 1998 both to Novartis); G. Bold et al., J. Med. Chem. 41, 3387 (1998); of bisulfate salt: J. Singh et al., WO 9936404; eidem, US 6087383 (1999, 2000 both to Bristol-Myers Squibb); Z. Xu et al., Org. Process Res. Dev. 6, 323 (2002). Comparative anti-HIV activity: B. S. Robinson et al., Antimicrob. Agents Chemother. 44, 2093 (2000). HPLC determn in plasma: E. Cateau et al., J. Pharm. Biomed. Anal. 39, 791 (2005). Clinical evaluation in HIV: I. Sanne et al., J. Acquired Immune Defic. Synd. 32, 18 (2003). Review of pharmacology and clinical efficacy in HIV: C. Le Tiec et al., Clin. Pharmacokinet. 44, 1035-1050 (2005); T. S. Harrison, L. J. Scott, Drugs 65, 2309-2336 (2005).
Properties: Crystals from ethanol/water, mp 207-209°. [a]D -47° (c = 1 in ethanol). Insol in water (<1 mg/ml at 24°).
Melting point: mp 207-209°
Optical Rotation: [a]D -47° (c = 1 in ethanol)
 
Derivative Type: Sulfate
CAS Registry Number: 229975-97-7
Trademarks: Reyataz (BMS)
Molecular Formula: C38H52N6O7.H2SO4
Molecular Weight: 802.93
Percent Composition: C 56.84%, H 6.78%, N 10.47%, O 21.92%, S 3.99%
Properties: Crystals from ethanol + heptane, mp 195.0°, or acetone, mp 198-199° (dec). [a]D22 -46.1° (c = 1 in 1:1 CH3OH/H2O, pH = 2.6). Soly in water: 4-5 mg/ml.
Melting point: mp 195.0°, or acetone; mp 198-199° (dec)
Optical Rotation: [a]D22 -46.1° (c = 1 in 1:1 CH3OH/H2O, pH = 2.6)
 
Therap-Cat: Antiviral.
Keywords: Antiviral; Peptidomimetics.

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