Structure via PubChem · Public domain (PubChem)
doxifluridine
Sign in to saveDoxifluridine (5'-deoxy-5-fluorouridine) is a second generation nucleoside analog prodrug developed by Roche and used as a cytostatic agent in chemotherapy in several Asian countries including China and South Korea. Doxifluridine is not FDA-approved for use in the USA. It is currently being evaluated in several clinical trials as a stand-alone or combination therapy treatment.
Chemical data
- Formula
- C9H11FN2O5
- Molecular weight
- 246.19 g/mol
- IUPAC name
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
- SMILES
- C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(=O)NC2=O)F)O)O
- InChIKey
- ZWAOHEXOSAUJHY-ZIYNGMLESA-N
- XLogP
- -1.7
- Polar surface area
- 99.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- gastric cancer
via ChEMBL · EBI
Research
812 papers- Doxifluridine effectively kills antibiotic-resistant Staphylococcus aureus in chronic obstructive pulmonary disease.Microbiology spectrum · 2024
- [Doxifluridine for treatment of colorectal cancer].Nihon rinsho. Japanese journal of clinical medicine · 2003
- Doxifluridine in advanced colorectal cancer.Journal of surgical oncology. Supplement · 1991
- Doxifluridine-based pharmacosomes delivering miR-122 as tumor microenvironments-activated nanoplatforms for synergistic treatment of hepatocellular carcinoma.Colloids and surfaces. B, Biointerfaces · 2021
- Doxifluridine versus Tegafur/Gimeracil/Oteracil (S-1) as adjuvant chemotherapy for patients with gastric cancer after gastrectomy: A propensity score-matched analysis.Asian journal of surgery · 2023
via PubMed
Wikidata facts
- Mass
- 246.065
- Has use
- medication
Show 5 more facts
- chemical formula
- C₉H₁₁FN₂O₅
- canonical SMILES
- CC1C(C(C(O1)N2C=C(C(=O)NC2=O)F)O)O
- isomeric SMILES
- C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(=O)NC2=O)F)O)O
- subject has role
- Orexigenic
- Commons category
- Doxifluridine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Biology
- Side effects
- Brand names
- References
Doxifluridine (5'-deoxy-5-fluorouridine) is a second generation nucleoside analog prodrug developed by Roche and used as a cytostatic agent in chemotherapy in several Asian countries including China and South Korea. Doxifluridine is not FDA-approved for use in the USA. It is currently being evaluated in several clinical trials as a stand-alone or combination therapy treatment.
==Biology== 5-Fluorouracil (5-FU), the nucleobase of doxifluridine, is currently an FDA-approved antimetabolite. 5-FU is normally administered intravenously to prevent its degradation by dihydropyrimidine dehydrogenase in the gut wall. Doxifluridine is a fluoropyrimidine derivative of 5-FU, thus a second-generation nucleoside prodrug. Doxifluridine was designed to improve oral bioavailability in order to avoid dihydropyrimidine dehydrogenase degradation in the digestive system.
Excerpted from Wikipedia’s “doxifluridine” article, available under the CC BY-SA 4.0 licence.