CHEBI:31348 - capecitabine

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ChEBI Name capecitabine
ChEBI ID CHEBI:31348
Definition A carbamate ester that is cytidine in which the hydrogen at position 5 is replaced by fluorine and in which the amino group attached to position 4 is converted into its N-(penyloxy)carbonyl derivative. Capecitabine is a antineoplastic agent used in the treatment of cancers.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H22FN3O6
Net Charge 0
Average Mass 359.35010
Monoisotopic Mass 359.14926
InChI InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
InChIKey GAGWJHPBXLXJQN-UORFTKCHSA-N
SMILES CCCCCOC(=O)Nc1nc(=O)n(cc1F)[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O
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.
Application(s): 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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing capecitabine (CHEBI:31348) has role antimetabolite (CHEBI:35221)
capecitabine (CHEBI:31348) has role antineoplastic agent (CHEBI:35610)
capecitabine (CHEBI:31348) has role prodrug (CHEBI:50266)
capecitabine (CHEBI:31348) is a carbamate ester (CHEBI:23003)
capecitabine (CHEBI:31348) is a cytidines (CHEBI:23524)
capecitabine (CHEBI:31348) is a organofluorine compound (CHEBI:37143)
IUPAC Name
5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine
INNs Sources
capecitabina ChEBI
capécitabine ChEBI
capecitabine KEGG DRUG
capecitabinum ChEBI
Synonyms Sources
(1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester KEGG COMPOUND
Capecitabin ChEBI
pentyl 1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate ChemIDplus
Pentyl [1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate IUPAC
Brand Name Source
Xeloda DrugBank
Manual Xrefs Databases
480 DrugCentral
C12650 KEGG COMPOUND
Capecitabine Wikipedia
D01223 KEGG DRUG
DB01101 DrugBank
HMDB0015233 HMDB
LSM-5705 LINCS
View more database links
Registry Numbers Types Sources
154361-50-9 CAS Registry Number ChemIDplus
8583270 Reaxys Registry Number Reaxys
Last Modified
28 April 2020