Tenofovir
Title: Tenofovir
CAS Registry Number: 147127-20-6
CAS Name: [[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic acid
Additional Names: (R)-9-(2-phosphonomethoxypropyl)adenine; (R)-PMPA
Manufacturers' Codes: GS-1278
Molecular Formula: C9H14N5O4P
Molecular Weight: 287.21
Percent Composition: C 37.64%, H 4.91%, N 24.38%, O 22.28%, P 10.78%
Literature References: Acyclic phosphonate nucleotide analog; reverse transcriptase inhibitor. Prepn: I. Rosenberg et al., Collect. Czech. Chem. Commun. 53, 2753 (1988); A. Holy et al., ibid. 60, 1390 (1995); L. M. Schultze et al., Tetrahedron Lett. 39, 1853 (1998). Prepn of ester prodrug: M. N. Arimilli et al., Antiviral Chem. Chemother. 8, 557 (1997); idem et al., WO 9804569; eidem, US 5922695 (1998, 1999 both to Gilead Sci.). Antiretroviral activity in vitro: J. Balzarini et al., Biochem. Biophys. Res. Commun. 219, 337 (1996). Metabolism and pharmacokinetics of prodrugs: J.-P. Shaw et al., Pharm. Res. 14, 1824 (1997). Clinical trial in HIV-infected patients: J. E. Gallant et al., J. Am. Med. Assoc. 292, 191 (2004).
Properties: Crystals from boiling water + ethanol, mp 279°. [a]D +21° (c = 1 in 0.1M HCl).
Melting point: mp 279°
Optical Rotation: [a]D +21° (c = 1 in 0.1M HCl)
 
Derivative Type: Bis(isopropyloxycarbonyloxymethyl) ester
CAS Registry Number: 201341-05-1
CAS Name: 5-[[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]-2,4,6,8-tetraoxa-5-phosphanononanedioic acid bis(1-methylethyl) ester 5-oxide
Additional Names: tenofovir disoproxil; (R)-bis(POC)PMPA
Molecular Formula: C19H30N5O10P
Molecular Weight: 519.44
Percent Composition: C 43.93%, H 5.82%, N 13.48%, O 30.80%, P 5.96%
Properties: Log P (1-octanol/aqueous phosphate buffer, pH 6.5): 1.3.
Log P: Log P (1-octanol/aqueous phosphate buffer, pH 6.5): 1.3
 
Derivative Type: Disoproxil fumarate
CAS Registry Number: 202138-50-9
Additional Names: Tenofovir DF
Manufacturers' Codes: GS-4331-05
Trademarks: Viread (Gilead)
Molecular Formula: C19H30N5O10P.C4H4O4
Molecular Weight: 635.51
Percent Composition: C 43.47%, H 5.39%, N 11.02%, O 35.25%, P 4.87%
Properties: White, fine, powder-like crystals.
 
Therap-Cat: Antiviral.
Keywords: Reverse Transcriptase Inhibitor; Antiviral; Purines/Pyrimidinones.

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