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CAS No 320-67-2 , 5-Azacytidine

  • Name: 5-Azacytidine
  • Synonyms: 4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one; 5-AC; 5-AZCR;4-amino-1-beta-D-ribofuranosyl-1,3,5-triazin-2(1H)-one; nci-c01569; Azacitidine; Azacytidine; 5-AZAC;5-Azacytidine; wr 183027; ladakamycin; 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; antibioticu18496; 4-amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one; u18496; 4-amino-1-beta-d-ribofuranosyl-s-triazin-2(1h)-on; 5 AZC; nsc-102816; mylosar; u 18496; Antibiotic u 18496; 5-triazin-2(1h)-one,4-amino-1-beta-d-ribofuranosyl-3;
  • CAS Registry Number:
  • Melting Point: 228-230 ºC
  • Flash Point: 277 ºC
  • Boiling Point: 534.5 ºC at 760 mmHg
  • Density: 2.08 g/cm3
  • Refractive index: 1.823
  • Alpha: 40 º (C=1, H2O 22 ºC)
  • Water Solubility: 0.5-1.0 G/100 ML AT 21 ºC
  • Safety Statements: R45;R46;R22
  • Hazard Symbols: T: Toxic;
  • Flash Point: 277 ºC
  • EINECS: 206-280-2
  • Molecular Weight: 244.21
  • InChI: InChI=1/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
  • Risk Statements: S53;S22;S36/37/39;S45
  • Molecular Formula: C8H12N4O5
  • Molecular Structure:CAS No:320-67-2 5-Azacytidine

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References of 5-Azacytidine
Title: Azacitidine
CAS Registry Number: 320-67-2
CAS Name: 4-Amino-1-b-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
Synonyms: 5-azacytidine; 5-AzaC; ladakamycin
Manufacturers' Codes: U-18496; NSC-102816
Trademarks: Mylosar (formerly); Vidaza (Pharmion)
Molecular Formula: C8H12N4O5
Molecular Weight: 244.20
Percent Composition: C 39.35%, H 4.95%, N 22.94%, O 32.76%
Literature References: DNA methylation inhibitor; analog of the pyrimidine nucleoside, cytidine, q.v. Chemical synthesis: A. Piskala, F. Sorm, Collect. Czech. Chem. Commun. 29, 2060 (1964); M. W. Winkley, R. K. Robins, J. Org. Chem. 35, 491 (1970). Production by fermentation of Streptoverticillium ladakanus and activity: L. J. Hanka et al., Antimicrob. Agents Chemother. 1966, 619; M. E. Bergy, R. R. Herr, ibid. 625. HPLC determn in pharmaceutical prepns: L. D. Kissinger, N. L. Stemm, J. Chromatogr. 353, 309 (1986). Toxicology study: P. E. Palm, C. J. Kensler, U.S. Clearinghouse Fed. Sci. Tech. Inform. (PB-194791, 1970) 191 pp., C.A. 75, 33704j (1971). Review of clinical experience in acute nonlymphocytic leukemia: A. B. Glover et al., Cancer Treat. Rep. 71, 737-746 (1987); of mechanism of action: A. B. Glover, B. Leyland-Jones, ibid. 959-964. Review of carcinogenic risk: IARC Monographs 50, 47-63 (1990). Clinical efficacy in b-thalassemia: C. H. Lowrey, A. W. Nienhuis, N. Engl. J. Med. 329, 845 (1993); in myelodysplastic syndrome: L. R. Silverman et al., J. Clin. Oncol. 20, 2429 (2002); A. B. Kornblith et al., ibid. 2441.
Properties: Crystals from aq ethanol, mp 235-237° (dec). [a]D26 +22.4° (c = 1 in water). uv max (water): 241 nm (e 8767); (0.01N HCl): 249 nm (e 3077); (0.01N KOH): 223 nm (e 24200). Soly (mg/ml): 40 warm water, 14 cold water, 28 0.1N HCl, 43 0.1N NaOH, 52.7 DMSO, 1 acetone, 1 chloroform, 1 hexane. LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler).
Melting point: mp 235-237° (dec)
Optical Rotation: [a]D26 +22.4° (c = 1 in water)
Absorption maximum: uv max (water): 241 nm (e 8767); (0.01N HCl): 249 nm (e 3077); (0.01N KOH): 223 nm (e 24200)
Toxicity data: LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler)
CAUTION: This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-24.
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.