| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H12FN3O4 |
| Molecular Weight | 245.2077 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1F)[C@H]2C[C@H](O)[C@@H](CO)O2
InChI
InChIKey=IDYKCXHJJGMAEV-RRKCRQDMSA-N
InChI=1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1
5-Fluoro-2-deoxycytidine is a fluorinated pyrimidine analog antimetabolite with potential antineoplastic activity. As a prodrug, 5-fluoro-2-deoxycytidine is converted by intracellular deaminases to the cytotoxic agent 5-fluorouracil (5-FU). 5-FU is subsequently metabolized to active metabolites including 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). FdUMP binds to and inhibits thymidylate synthase, thereby reducing the production of thymidine monophosphate, which leads to depletion of thymidine triphosphate and the inhibition of DNA synthesis and cell division. FUTP competes with uridine triphosphate (UTP) for incorporation into the RNA strand, which results in the inhibition of RNA and protein synthesis and cell proliferation. 5-Fluoro-2-deoxycytidine undergoing trials to test its effectiveness in treating cancer that has not responded to standard therapies.
Originator
Approval Year
Sourcing
PubMed
Sample Use Guides
5-Fluoro-2-Deoxycytidine (100 mg/m2) + Tetrahydrouridine (350 mg/m2) administered 5 days/week for 2 weeks in 28-daycycles
Route of Administration:
Intravenous
HCT116 and U2OS cells were used for activity evaluation. Cells were split at 1Ч103 cells per well in 96-well plate. After 24 h cells were treated with drugs (5-Fluoro-2-deoxycytidine 0.1-10mkM) and cultured for 72 h. 25 μg MTT was then added to each well and cells incubated for 4 h at 37°C. The medium with the formazan sediment was dissolved in 50% DMF and 30% SDS (pH4.7). The absorption was read at 570nM.
METABOLITE ACTIVE (PRODRUG)
SUBSTANCE RECORD
