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Substance Name: Decitabine [USAN:INN:BAN]
RN: 2353-33-5
UNII: 776B62CQ27
InChIKey: XAUDJQYHKZQPEU-KVQBGUIXSA-N

Notes

  • An azacitidine derivative and antineoplastic antimetabolite. It inhibits DNA methyltransferase to re-activate silent genes, limiting METASTASIS and NEOPLASM DRUG RESISTANCE. Decitabine is used in the treatment of MYELODISPLASTIC SYNDROMES, and ACUTE MYELOID LEUKEMIA.
  • NCI: decitabine. A cytidine antimetabolite analogue with potential antineoplastic activity. Decitabine incorporates into DNA and inhibits DNA methyltransferase, resulting in hypomethylation of DNA and intra-S-phase arrest of DNA replication. (NCI Thesaurus)

Molecular Formula

  • C8-H12-N4-O4

Molecular Weight

  • 228.2068
 

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Teratogens

Names and Synonyms

Name of Substance

  • Decitabine
  • Decitabine [USAN:INN:BAN]

MeSH Heading

  • Decitabine

Synonyms

  • 2-Deoxyazacytidine
  • 2-Desoxy-5-azacytidine
  • 4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-s-triazin-2(1H)-one
  • 5-Aza-2'-deoxycytidine
  • 5-Aza-deoxycytidine
  • 5-Azadeoxycytidine
  • BRN 0617982
  • CCRIS 8227
  • DAC
  • Dacogen
  • Decitabine
  • EINECS 219-089-4
  • JNJ 30979754
  • JNJ-30979754
  • NSC 127716
  • UNII-776B62CQ27

Systematic Names

  • 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-
  • 4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one
  • s-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-

Registry Numbers

CAS Registry Number

  • 2353-33-5

FDA UNII

  • 776B62CQ27

Other Registry Numbers

  • 105597-46-4
  • 123795-43-7

System Generated Number

  • 0002353335

Structure Descriptors

InChI

InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1

InChIKey

XAUDJQYHKZQPEU-KVQBGUIXSA-N

Smiles

NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 190mg/kg (190mg/kg)   Cancer Research. Vol. 37, Pg. 3684, 1977.
mouse LD50 intravenous 22mg/kg (22mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: LEUKOPENIA		 Drug and Chemical Toxicology. Vol. 4, Pg. 373, 1981.