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CHEBI:31348 - capecitabine

ChEBI IDCHEBI:31348
ChEBI Namecapecitabine
Stars
DefinitionA 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.
Last Modified28 April 2020
DownloadsMolfile
FormulaC15H22FN3O6
Net Charge0
Average Mass359.354
Monoisotopic Mass359.14926
SMILESCCCCCOC(=O)Nc1nc(=O)n([C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)cc1F
InChIInChI=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
InChIKeyGAGWJHPBXLXJQN-UORFTKCHSA-N
Wikipedia
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)
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  Source
capecitabineKEGG DRUG
capecitabinaChEBI
capécitabineChEBI
capecitabinumChEBI
Synonyms  Source
(1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl esterKEGG COMPOUND
pentyl 1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamateChemIDplus
Pentyl [1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamateIUPAC
CapecitabinChEBI
Brand Name  Source
XelodaDrugBank
Manual XrefsDatabases
C12650KEGG COMPOUND
D01223KEGG DRUG
DB01101DrugBank
CapecitabineWikipedia
HMDB0015233HMDB
LSM-5705LINCS
480DrugCentral
Registry NumbersSources
Reaxys:8583270Reaxys
CAS:154361-50-9KEGG COMPOUND
CAS:154361-50-9ChemIDplus