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Substance Name: Azacitidine [USAN:INN:BAN]
RN: 320-67-2
UNII: M801H13NRU
InChIKey: NMUSYJAQQFHJEW-KVTDHHQDSA-N

Note

  • A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.

Molecular Formula

  • C8-H12-N4-O5

Molecular Weight

  • 244.206
 

Classification Codes

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2A
  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Azacitidine
  • Azacitidine [USAN:INN:BAN]

MeSH Heading

  • Azacitidine

Synonyms

  • 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one
  • 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one
  • 5-AC
  • 5-Azacytidine
  • 5-AZCR
  • Antibiotic U 18496
  • Azacitidina
  • Azacitidina [INN-Spanish]
  • Azacitidine
  • Azacitidinum
  • Azacitidinum [INN-Latin]
  • Azacytidine
  • BRN 0620461
  • CCRIS 60
  • EINECS 206-280-2
  • HSDB 6879
  • Ladakamycin
  • Mylosar
  • NCI-C01569
  • NSC 102816
  • NSC-102816
  • U 18496
  • U-18,496
  • UNII-M801H13NRU
  • Vidaza
  • WR-183027

Systematic Names

  • 1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-
  • 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one
  • 5-Azacytidine
  • s-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl- (8CI)

Superlist Names

  • 5-Azacytidine
  • Azacitidine

Registry Numbers

CAS Registry Number

  • 320-67-2

FDA UNII

  • M801H13NRU

System Generated Number

  • 0000320672

Structure Descriptors

InChI

1S/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

InChIKey

NMUSYJAQQFHJEW-KVTDHHQDSA-N

Smiles

n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)nc1)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 100mg/kg (100mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
dog LD50 intravenous 7200ug/kg (7.2mg/kg) BLOOD: OTHER CHANGES Advances in Pharmacology and Chemotherapy. Vol. 14, Pg. 285, 1977.
mouse LD50 intraperitoneal 68mg/kg (68mg/kg)   Experientia. Vol. 22, Pg. 53, 1966.
mouse LD50 intravenous 229mg/kg (229mg/kg) BEHAVIORAL: ATAXIA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Technical Information Service. Vol. PB84-211432,
mouse LD50 oral 572mg/kg (572mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 382, 1971.
quail LD50 oral > 100mg/kg (100mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
women TDLo intravenous 500ug/kg (0.5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 413, 1972.
women TDLo intravenous 6mg/kg/10D-I (6mg/kg) BLOOD: LEUKOPENIA

BLOOD: AGRANULOCYTOSIS
Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 413, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 229 deg C   EXP
log P (octanol-water) -3.830 (none)   EST
Water Solubility 8.90E+04 mg/L 25 EST
Vapor Pressure 4.10E-12 mm Hg 25 EST
Henry's Law Constant 3.80E-21 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.72E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.