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capecitabine (CHEBI:31348)

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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 to 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.
Supplier Information
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Formula Source
C15H22FN3O6 KEGG COMPOUND
Net Charge 0
Average Mass 359.35010
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): 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.
View more on the 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
Database Links Databases
C12650 KEGG COMPOUND
Capecitabine Wikipedia
D01223 KEGG DRUG
DB01101 DrugBank
HMDB15233 HMDB
View more database links
Registry Numbers Types Sources
154361-50-9 CAS Registry Number ChemIDplus
8583270 Reaxys Registry Number Reaxys
Last Modified
12 May 2014

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