Home > Name List By 1 > 1-[(2S,3R,4S, 5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine- 2,4-dione

CAS No 163252-36-6 , 1-[(2S,3R,4S,
5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-
2,4-dione

  • Name: 1-[(2S,3R,4S,
    5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-
    2,4-dione
  • Synonyms: L-FMAU; 163252-36-6; Levovir; 2'-fluoro-5-methyl-b-l-arabinofuranosyluracil;1-[(2S,3R,4S,
    5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-
    2,4-dione;
  • CAS Registry Number:
  • Flash Point: °C
  • Boiling Point: °Cat760mmHg
  • Density: 1.55g/cm3
  • Refractive index: 1.592
  • Flash Point: °C
  • Molecular Weight: 260.219023
  • InchiKey: GBBJCSTXCAQSSJ-XQXXSGGOSA-N
  • InChI: InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/
    h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m0/s1
  • Molecular Formula: C10H13FN2O5
  • Molecular Structure:CAS No:163252-36-6 1-[(2S,3R,4S,<br />5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-<br />2,4-dione

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References of 1-[(2S,3R,4S,
5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-
2,4-dione
Title: Clevudine
CAS Registry Number: 163252-36-6
CAS Name: 1-(2-Deoxy-2-fluoro-b-L-arabinofuranosyl)-5-methyl-2,4-(1H,3H)-pyrimidinedione
Synonyms: 1-(2-deoxy-2-fluoro-b-L-arabinofuranosyl)thymine; 2¢-fluoro-5-methyl-b-L-arabinofuranosyluridine; L-FMAU
Molecular Formula: C10H13FN2O5
Molecular Weight: 260.22
Percent Composition: C 46.16%, H 5.04%, F 7.30%, N 10.77%, O 30.74%
Literature References: Nucleoside analog; specific inhibitor of viral DNA synthesis. Prepn: C. K. Chu et al., WO 9520595; eidem, US 5587362 (1995, 1996 both to Univ. Georgia Res. Found.; Yale Univ.); T. Ma et al., J. Med. Chem. 39, 2835 (1996). Synthesis: M. L. Sznaidman et al., Nucleosides Nucleotides Nucleic Acids 21, 155 (2002). In vitro antiviral activity: C. K. Chu et al., Antimicrob. Agents Chemother. 39, 979 (1995). Pharmacokinetics: J. D. Wright et al., Pharm. Res. 12, 1350 (1995). Mechanism of action study: Y. Chong, C. K. Chu, Bioorg. Med. Chem. Lett. 12, 3459 (2002). Clinical evaluation in chronic hepatitis B: P. Marcellin et al., Hepatology 40, 140 (2004). Review of preclinical pharmacology: C. K. Chu et al. in Therapies for Viral Hepatitis, R. F. Schinazi et al., Eds. (Int. Med. Press, London, 1998) pp 303-312; of development and clinical experience: G. R. Painter et al. in Frontiers in Viral Hepatitis, R. F. Schinazi et al., Eds. (Elsevier, New York, 2003) pp 281-300.
Properties: Crystals from methanol/chloroform, mp 184-185°. [a]D25 -111.77° (c = 0.23 in methanol). uv max in water: 265.0 (pH 2), 265.5 (pH 7), 265.5 nm (pH 11) (e 9695, 9647, 7153). LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter).
Melting point: mp 184-185°
Optical Rotation: [a]D25 -111.77° (c = 0.23 in methanol)
Absorption maximum: uv max in water: 265.0 (pH 2), 265.5 (pH 7), 265.5 nm (pH 11) (e 9695, 9647, 7153)
Toxicity data: LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter)
 
Derivative Type: Triphosphate
CAS Registry Number: 174625-00-4
Synonyms: L-FMAU-TP
Molecular Formula: C10H16FN2O14P3
Molecular Weight: 500.16
Percent Composition: C 24.01%, H 3.22%, F 3.80%, N 5.60%, O 44.78%, P 18.58%
 
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones.