Home > Name List By 4 > 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1, 3-oxathiolan-5-yl]pyrimidin-2-one

CAS No 143491-57-0 , 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,
3-oxathiolan-5-yl]pyrimidin-2-one

  • Name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,
    3-oxathiolan-5-yl]pyrimidin-2-one
  • Synonyms: 524W91; (-)-FTC; dOTFC;4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,
    3-oxathiolan-5-yl]pyrimidin-2-one; BW-524W91; Emtriva; 143491-57-0;Coviracil; BW524W91; Racivir;
  • CAS Registry Number:
  • Flash Point: 221.9ºC
  • Boiling Point: 443.3ºC at 760 mmHg
  • Density: 1.82 g/cm3
  • Refractive index: 1.731
  • Flash Point: 221.9ºC
  • Molecular Weight: 247.246703
  • InchiKey: XQSPYNMVSIKCOC-NTSWFWBYSA-N
  • InChI: InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,
    13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1
  • Molecular Formula: C8H10FN3O3S
  • Molecular Structure:CAS No:143491-57-0 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,<br />3-oxathiolan-5-yl]pyrimidin-2-one

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References of 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,
3-oxathiolan-5-yl]pyrimidin-2-one
Title: Emtricitabine
CAS Registry Number: 143491-57-0
CAS Name: 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
Synonyms: (-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one; (-)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; (-)-b-2￠,3￠-dideoxy-5-fluoro-3￠-thiacytidine; (-)-FTC
Manufacturers' Codes: 524W91; BW-524W91
Trademarks: Coviracil (Triangle); Emtriva (Gilead)
Molecular Formula: C8H10FN3O3S
Molecular Weight: 247.25
Percent Composition: C 38.86%, H 4.08%, F 7.68%, N 16.99%, O 19.41%, S 12.97%
Literature References: Reverse transcriptase inhibitor; nucleoside analog structurally related to lamivudine, q.v. Prepn: D. C. Liotta et al., WO 9214743 (1992 to Emory University); G. Dionne, US 5538975 (1996 to BioChem Pharma, Inc.); L. S. Jeong et al., J. Med. Chem. 36, 181 (1993). Absolute configuration: P. van Roey et al., Antiviral Chem. Chemother. 4, 369 (1993). HPLC-NMR determn of urinary metabolites: J. P. Shockcor et al., Xenobiotica 26, 189 (1996). Comparative efficacy of enantiomers vs HIV: R. F. Schinazi et al., Antimicrob. Agents Chemother. 36, 2423 (1992). Pharmacokinetics: L. W. Frick et al., ibid. 38, 2722 (1994). Mechanism of action study: J. Y. Feng et al., FASEB J. 13, 1511 (1999). Clinical study in combination with didanosine and efavirenz: J.-M. Molina et al., J. Infect. Dis. 182, 599 (2000). Review: P. Cahn, Expert Opin. Invest. Drugs 13, 55-68 (2004).
Properties: White solid from ether and methanol, mp 136-140°. [a]D25 -133.60° (c = 0.23 in MeOH). uv max (water): 287.8 nm (pH 2); 280.0 nm (pH 7); 279.8 nm (pH 11) (e 14210, 11090, 11810).
Melting point: mp 136-140°
Optical Rotation: [a]D25 -133.60° (c = 0.23 in MeOH)
Absorption maximum: uv max (water): 287.8 nm (pH 2); 280.0 nm (pH 7); 279.8 nm (pH 11) (e 14210, 11090, 11810)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor.