Molecular Identity
Doxifluridine
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
PubChem CID: 18343
Doxifluridine is a 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. It has a role as an antimetabolite, an antineoplastic agent and a prodrug. It is an organofluorine compound and a pyrimidine 5'-deoxyribonucleoside.
2D Structure
Properties
C9H11FN2O5
Molecular Formula
246.19
Molecular Weight
g/mol
246.0652
Exact Mass
Da
-1.7
XLogP
Drug-like (Lipinski: < 5)
99.1
TPSA
Good oral absorption (< 140 A²)
3
H-Bond Donors
6
H-Bond Acceptors
399
Complexity
SMILES
Canonical SMILES
SMILES: CC1C(C(C(O1)N2C=C(C(=O)NC2=O)F)O)OIsomeric SMILES
SMILES: C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(=O)NC2=O)F)O)OSynonyms(20)
doxifluridine5'-Deoxy-5-fluorouridine5-fluoro-5'-deoxyuridineFurtulon3094-09-5Uridine, 5'-deoxy-5-fluoro-Flutron5'-DfurDoxifluridinaDoxifluridinumFulturonDTXSID2022967Ro 219738Uridine-5'-deoxy-5-fluoro-1-(beta-D-5-Desoxyribofuranoxyl)-5-fluoruracil
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Doxifluridine
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