| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H11FN2O5 |
| Molecular Weight | 246.1924 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(F)C(=O)NC2=O
InChI
InChIKey=ZWAOHEXOSAUJHY-ZIYNGMLESA-N
InChI=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
| Molecular Formula | C9H11FN2O5 |
| Molecular Weight | 246.1924 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Doxifluridine is a 5-fluorouracil prodrug that is being tested for the treatment of cancer. The cleavage into 5-fluorouracil occurs enzymatically via a nucleoside phosphorylase. Thus, doxifluridine is not active by itself and its antitumor activity is related to its metabolic conversion into 5-fluorouracil. Doxifluridine has neurotoxic adverse effects.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
The cytotoxicity of Doxifluridine was determined in several cultured human tumor lines including tumors of the breast (47-DN, MCF-7), the colon (HCT-8), and the pancreas (Coto-357), as well as an osteosarcoma (MG-63) and a leukemia (HL-60). In vitro clonogenic assays were used to measure cytotoxicity following a 3hr drug exposure. Doxifluridine was less potent than was 5-fluorouracil or 5-fluoro-2'-deoxyuridine in all cells examined, exhibiting its best activity against the 47-DN [concentration that prevented 50% clonal growth compared to untreated control (LD50) = 32 uM] and MCF-7 (LD50= 35 uM) breast carcinomas and MG63 osteosarcoma (LD50 = 41 uM). Intermediate activity was observed against HCT-8 (LD50 = 200 uM)and Colo-357 (LD50 = 150 uM) gastrointestinal tumors. Doxifluridine had very poor activity against the HL-60 leukemia (LD50 = 470 uM).
