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CAS No 147127-20-6 , [(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid

  • Name: [(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid
  • Synonyms: D,L-Tenofovir; GNA & Tenofovir; Viread;[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid; (R)-PMPA; HHA & Tenofovir; Tenefovir; Apropovir;PMPA; Tenofovir; 147127-20-6;
  • CAS Registry Number:
  • Density: 1.79 g/cm3
  • Molecular Weight: 287.212322
  • InchiKey: SGOIRFVFHAKUTI-ZCFIWIBFSA-N
  • InChI: InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,
    16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,
    12)(H2,15,16,17)/t6-/m1/s1
  • Molecular Formula: C9H14N5O4P
  • Molecular Structure:CAS No:147127-20-6 [(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid

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    References of [(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid
    Title: Tenofovir
    CAS Registry Number: 147127-20-6
    CAS Name: [[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic acid
    Synonyms: (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
    Synonyms: 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
    Synonyms: 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.