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CHEBI:31521 - doxifluridine

ChEBI IDCHEBI:31521
ChEBI Namedoxifluridine
Stars
DefinitionA pyrimidine 5'-deoxyribonucleoside that is 5-fluorouridine in which the hydroxy group at the 5' position is replaced by a hydrogen. It is an oral prodrug of the antineoplastic agent 5-fluorouracil. Designed to circumvent the rapid degradation of 5-fluorouracil by dihydropyrimidine dehydrogenase in the gut wall, it is converted into 5-fluorouracil in the presence of pyrimidine nucleoside phosphorylase.
Secondary ChEBI IDCHEBI:74488
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC9H11FN2O5
Net Charge0
Average Mass246.194
Monoisotopic Mass246.06520
SMILESC[C@H]1O[C@@H](n2cc(F)c(=O)nc2=O)[C@H](O)[C@@H]1O
InChIInChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1
InChIKeyZWAOHEXOSAUJHY-ZIYNGMLESA-N
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:
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.
ChEBI Ontology
Outgoing Relation(s)
doxifluridine (CHEBI:31521) has role antimetabolite (CHEBI:35221)
doxifluridine (CHEBI:31521) has role antineoplastic agent (CHEBI:35610)
doxifluridine (CHEBI:31521) has role prodrug (CHEBI:50266)
doxifluridine (CHEBI:31521) is a organofluorine compound (CHEBI:37143)
doxifluridine (CHEBI:31521) is a pyrimidine 5'-deoxyribonucleoside (CHEBI:74494)
IUPAC Name 
5'-deoxy-5-fluorouridine
INNs  Source
doxifluridineChemIDplus
doxifluridinaChemIDplus
doxifluridinumChemIDplus
doxifluridineWHO MedNet
Synonyms  Source
Ro 21-9738ChemIDplus
1-(β-D-5-desoxyribofuranoxyl)-5-fluoruracilChemIDplus
5'-DfurChemIDplus
Ro 219738ChemIDplus
5'-DFURChEBI
5-fluoro-5'-deoxyuridineChEBI
Brand Name  Source
FurtulonKEGG DRUG
Manual XrefsDatabases
C12739KEGG COMPOUND
D01309KEGG DRUG
US4071680Patent
HMDB0060406HMDB
LSM-6359LINCS
958DrugCentral
Registry NumbersSources
Reaxys:890191Reaxys
CAS:3094-09-5KEGG COMPOUND
CAS:3094-09-5ChemIDplus
Citations