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CHEBI:74838 - ancitabine

ChEBI IDCHEBI:74838
ChEBI Nameancitabine
Stars
DefinitionAn organic heterotricyclic compound resulting from the formal condensation of the oxo group of cytidine to the 2' position with loss of water to give the corresponding cyclic ether. A prodrug, it is metabolised to the antineoplastic agent cytarabine, so is used to maintain a more constant antineoplastic action.
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC9H11N3O4
Net Charge0
Average Mass225.204
Monoisotopic Mass225.07496
SMILESN=c1ccn2c(n1)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]12
InChIInChI=1S/C9H11N3O4/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8/h1-2,4,6-8,10,13-14H,3H2/t4-,6-,7+,8-/m1/s1
InChIKeyBBDAGFIXKZCXAH-CCXZUQQUSA-N
Roles Classification
Biological Role:
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
ancitabine (CHEBI:74838) has role antimetabolite (CHEBI:35221)
ancitabine (CHEBI:74838) has role antineoplastic agent (CHEBI:35610)
ancitabine (CHEBI:74838) has role prodrug (CHEBI:50266)
ancitabine (CHEBI:74838) is a diol (CHEBI:23824)
ancitabine (CHEBI:74838) is a organic heterotricyclic compound (CHEBI:26979)
ancitabine (CHEBI:74838) is conjugate base of ancitabine(1+) (CHEBI:74842)
Incoming Relation(s)
ancitabine(1+) (CHEBI:74842) is conjugate acid of ancitabine (CHEBI:74838)
IUPAC Name 
(2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol
INNs  Source
ancitabinumChemIDplus
ancitabinaChemIDplus
ancitabineWHO MedNet
ancitabineChemIDplus
Synonyms  Source
2,2'-anhydroarabinosylcytosineChemIDplus
2,2'-anhydrocytidineChemIDplus
2,2'-O-cyclocytidineChemIDplus
anhydrocytidineChemIDplus
2,2'-cyclocytidineChemIDplus
cyclocytidineChEBI
Manual XrefsDatabases
US3463850Patent
212DrugCentral
Registry NumbersSources
Reaxys:669322Reaxys
CAS:31698-14-3ChemIDplus
Citations