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CHEBI:31348 - capecitabine

Default Structure
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
capecitabinaChEBI
capecitabineKEGG DRUG
capécitabineChEBI
capecitabinumChEBI
Synonyms  Source
(1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl esterKEGG COMPOUND
CapecitabinChEBI
Capecitabine accordChEMBL
Capecitabine medacChEMBL
Capecitabine sunChEMBL
Capecitabine tevaChEMBL
Brand Names  Source
Capecitabine component of xeliri capecitibineChEMBL
Capecitabine component of xeloxChEMBL
Ecansya (previously capecitabine krka)ChEMBL
XelodaDrugBank
Manual XrefsDatabases
480DrugCentral
C12650KEGG COMPOUND
CapecitabineWikipedia
D01223KEGG DRUG
DB01101DrugBank
HMDB0015233HMDB
LSM-5705LINCS
Registry NumbersSources
Reaxys:8583270Reaxys
CAS:154361-50-9ChemIDplus
CAS:154361-50-9KEGG COMPOUND
Citations