Abacavir
Title: Abacavir
CAS Registry Number: 136470-78-5
CAS Name: (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol
Additional Names: (-)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol
Manufacturers' Codes: 1592U89
Molecular Formula: C14H18N6O
Molecular Weight: 286.33
Percent Composition: C 58.73%, H 6.34%, N 29.35%, O 5.59%
Literature References: Nucleoside reverse transcriptase inhibitor (NRTI). Prepn: S. M. Daluge, EP 349242 (1990 to Wellcome Found.); idem, US 5034394 (1991 to Burroughs Wellcome). Asymmetric synthesis: M. T. Crimmins, B. W. King, J. Org. Chem. 61, 4192 (1996). Pharmacology and biological profile: S. M. Daluge et al., Antimicrob. Agents Chemother. 41, 1082 (1997). Review of antiviral activity and clinical evaluations: R. H. Foster, D. Faulds, Drugs 55, 729-736 (1998). Clinical trial of triple nucleoside regimen in HIV patients: S. Staszewski et al., J. Am. Med. Assoc. 285, 1155 (2001).
Properties: White solid foam from acetonitrile, mp 165°. uv max (pH 1): 296, 255 nm (e 14000, 10700); uv max (pH 7): 284, 259 nm (e 15900, 9200); uv max (pH 13): 284, 259 nm (e 15800, 9100). [a]D20 -59.7°; [a]43620 -127.8°; [a]36520 -218.1° (c = 0.15 in methanol). Log P (1-octanol/0.1M sodium phosphate): 1.22 ±0.03 (pH 7.4). pKa 5.01. Soly in water (25°): >80 mM (pH 7).
Melting point: mp 165°
pKa: pKa 5.01
Optical Rotation: [a]D20 -59.7°; [a]43620 -127.8°; [a]36520 -218.1° (c = 0.15 in methanol)
Log P: Log P (1-octanol/0.1M sodium phosphate): 1.22 ±0.03 (pH 7.4)
Absorption maximum: uv max (pH 1): 296, 255 nm (e 14000, 10700); uv max (pH 7): 284, 259 nm (e 15900, 9200); uv max (pH 13): 284, 259 nm (e 15800, 9100)
 
Derivative Type: Sulfate
CAS Registry Number: 188062-50-2
Trademarks: Ziagen (GSK)
Molecular Formula: (C14H18N6O)2.H2SO4
Molecular Weight: 670.74
Percent Composition: C 50.14%, H 5.71%, N 25.06%, O 14.31%, S 4.78%
 
Therap-Cat: Antiviral.
Keywords: Reverse Transcriptase Inhibitor; Antiviral; Purines/Pyrimidinones.

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