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CHEBI:145429 - sapacitabine

ChEBI IDCHEBI:145429
ChEBI Namesapacitabine
Stars
DefinitionA nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical development for the treatment of acute myeloid leukemia (AML).
Last Modified20 November 2019
SubmitterAdnan
DownloadsMolfile
FormulaC26H42N4O5
Net Charge0
Average Mass490.645
Monoisotopic Mass490.31552
SMILESCCCCCCCCCCCCCCCC(=O)Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2C#N)c(=O)n1
InChIInChI=1S/C26H42N4O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(32)28-22-16-17-30(26(34)29-22)25-20(18-27)24(33)21(19-31)35-25/h16-17,20-21,24-25,31,33H,2-15,19H2,1H3,(H,28,29,32,34)/t20-,21+,24-,25+/m0/s1
InChIKeyLBGFKUUHOPIEMA-PEARBKPGSA-N
Wikipedia
Roles Classification
Biological Roles:
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.
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
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)
sapacitabine (CHEBI:145429) has functional parent CNDAC (CHEBI:145435)
sapacitabine (CHEBI:145429) has functional parent hexadecanoic acid (CHEBI:15756)
sapacitabine (CHEBI:145429) has role antimetabolite (CHEBI:35221)
sapacitabine (CHEBI:145429) has role antineoplastic agent (CHEBI:35610)
sapacitabine (CHEBI:145429) has role DNA synthesis inhibitor (CHEBI:59517)
sapacitabine (CHEBI:145429) has role prodrug (CHEBI:50266)
sapacitabine (CHEBI:145429) is a nitrile (CHEBI:18379)
sapacitabine (CHEBI:145429) is a nucleoside analogue (CHEBI:60783)
sapacitabine (CHEBI:145429) is a secondary carboxamide (CHEBI:140325)
IUPAC Name 
1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-4-(hexadecanoylamino)pyrimidin-2(1H)-one
INNs  Source
sapacitabinumWHO MedNet
sapacitabinaWHO MedNet
sapacitabineWHO MedNet
sapacitabineWHO MedNet
Synonyms  Source
CS-682DrugBank
CYC-682DrugBank
CYC682DrugBank
CS 682ChemIDplus
CS682ChemIDplus
CYC 682ChemIDplus
Manual XrefsDatabases
SapacitabineWikipedia
DB06365DrugBank
D09722KEGG DRUG
Registry NumbersSources
CAS:151823-14-2ChemIDplus
Citations