CHEBI:145429 - sapacitabine

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ChEBI Name sapacitabine
ChEBI ID CHEBI:145429
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H42N4O5
Net Charge 0
Average Mass 490.645
Monoisotopic Mass 490.31552
InChI InChI=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
InChIKey LBGFKUUHOPIEMA-PEARBKPGSA-N
SMILES O1[C@@H]([C@H]([C@@H]([C@@H]1N2C(N=C(C=C2)NC(CCCCCCCCCCCCCCC)=O)=O)C#N)O)CO
Roles Classification
Biological Role(s): 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.
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
sapacitabina WHO MedNet
sapacitabine WHO MedNet
sapacitabine WHO MedNet
sapacitabinum WHO MedNet
Synonyms Sources
CS 682 ChemIDplus
CS-682 DrugBank
CS682 ChemIDplus
CYC 682 ChemIDplus
CYC-682 DrugBank
CYC682 DrugBank
N-(1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl)hexadecanamide ChemIDplus
N-[1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-2-oxo-1,2-dihydropyrimidine-4-yl]hexadecanamide ChEBI
PCNDAC ChEBI
Manual Xrefs Databases
D09722 KEGG DRUG
DB06365 DrugBank
Sapacitabine Wikipedia
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Registry Number Type Source
151823-14-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16502355 PubMed citation Europe PMC
16788861 PubMed citation Europe PMC
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Last Modified
20 November 2019