Azacitidine

Title: Azacitidine
CAS Registry Number: 320-67-2
CAS Name: 4-Amino-1-b-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
Additional Names: 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.
Azaconazole Azacosterol Azacyclonol Azafenidin Azafrin

Azacitidine
Azacitidine.svg
Systematic (IUPAC) name
4-amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
Clinical data
Trade names Vidaza
AHFS/Drugs.com monograph
MedlinePlus a607068
Pregnancy cat. D (US), X (Aus)
Legal status  ?
Routes SubQ, IV
Pharmacokinetic data
Metabolism possible hepatic metabolism, mostly urinary excretion
Half-life 4 hr.[1]
Identifiers
CAS number 320-67-2 YesY
ATC code L01BC07
PubChem CID 9444
DrugBank DB00928
ChemSpider 9072 YesY
UNII M801H13NRU YesY
KEGG D03021 YesY
ChEBI CHEBI:2038 YesY
ChEMBL CHEMBL1489 YesY
Synonyms 5-azacytidine
Chemical data
Formula C8H12N4O5 
Mol. mass 244.205 g/mol
 YesY (what is this?)  (verify)

Azacitidine (INN) or 5-azacytidine, sold under the trade name Vidaza, is a chemical analogue of cytidine, a nucleoside present in DNA and RNA. Azacitidine and its deoxy derivative, decitabine (also known as 5-aza-2′deoxycytidine), are used in the treatment of myelodysplastic syndrome. Both drugs were first synthesized in Czechoslovakia as potential chemotherapeutic agents for cancer.[2]