Home > Name List By 4 > 4-amino-1-[(2R,4R,5R)-3, 3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

CAS No 95058-81-4 , 4-amino-1-[(2R,4R,5R)-3,
3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

  • Name: 4-amino-1-[(2R,4R,5R)-3,
    3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
  • Synonyms: Gemtro; Gemcitabinum [INN-Latin]; 2',2'-Difluorodeoxycytidine;dFdC; DDFC; Gemcitabina [INN-Spanish]; 95058-81-4; Gemcin;4-amino-1-[(2R,4R,5R)-3,
    3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;
  • CAS Registry Number:
  • Density: 1.84 g/cm3
  • Refractive index: 1.652
  • Safety Statements: 25-26-36/37-53
  • Hazard Symbols: Xn: Harmful;Xi: Irritant;
  • Molecular Weight: 263.198146
  • InchiKey: SDUQYLNIPVEERB-QPPQHZFASA-N
  • InChI: InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/
    h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
  • Risk Statements: 21-36/38-46-62-63
  • Molecular Formula: C9H11F2N3O4
  • Molecular Structure:CAS No:95058-81-4 4-amino-1-[(2R,4R,5R)-3,<br />3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

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References of 4-amino-1-[(2R,4R,5R)-3,
3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Title: Gemcitabine
CAS Registry Number: 95058-81-4
CAS Name: 2￠-Deoxy-2￠,2￠-difluorocytidine
Synonyms: 1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose; dFdC; dFdCyd
Manufacturers' Codes: LY-188011
Trademarks: Gemzar (Lilly)
Molecular Formula: C9H11F2N3O4
Molecular Weight: 263.20
Percent Composition: C 41.07%, H 4.21%, F 14.44%, N 15.97%, O 24.32%
Literature References: Prepn: L. W. Hertel, GB 2136425; idem, US 4808614 (1984, 1989 both to Lilly); L. W. Hertel et al., J. Org. Chem. 53, 2406 (1988); T. S. Chou et al., Synthesis 1992, 565. Antitumor activity: L. W. Hertel et al., Cancer Res. 50, 4417 (1990). Mode of action study: V. W. T. Ruiz et al., Biochem. Pharmacol. 46, 762 (1993). Clinical pharmacokinetics and toxicity: J. L. Abbruzzese et al., J. Clin. Oncol. 9, 491 (1991). Review of clinical studies: B. Lund et al., Cancer Treat. Rev. 19, 45-55 (1993).
Properties: Crystals from water, pH 8.5. [a]365 +425.36°; [a]D +71.51° (c = 0.96 in methanol). uv max (ethanol): 234, 268 (e 7810, 8560). LD10 i.v. in rats: 200 mg/m2 (Abbruzzese).
Optical Rotation: [a]365 +425.36°; [a]D +71.51°
Absorption maximum: uv max (ethanol): 234, 268 (e 7810, 8560)
Toxicity data: LD10 i.v. in rats: 200 mg/m2 (Abbruzzese)
 
Derivative Type: Hydrochloride
CAS Registry Number: 122111-03-9
Molecular Formula: C9H11F2N3O4.HCl
Molecular Weight: 299.66
Percent Composition: C 36.07%, H 4.04%, F 12.68%, N 14.02%, O 21.36%, Cl 11.83%
Properties: Crystals from water-acetone, mp 287-292° (dec). [a]D +48°; [a]365 +257.9° (c = 1.0 in deuterated water). uv max (water): 232, 268 nm (e 7960, 9360).
Melting point: mp 287-292° (dec)
Optical Rotation: [a]D +48°; [a]365 +257.9° (c = 1.0 in deuterated water)
Absorption maximum: uv max (water): 232, 268 nm (e 7960, 9360)
 
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.