Details
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25567350Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT00978250 | https://www.ncbi.nlm.nih.gov/pubmed/19836229 | https://clinicaltrials.gov/ct2/show/NCT01041443 | https://www.ncbi.nlm.nih.gov/pubmed/23397046
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25567350
Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT00978250 | https://www.ncbi.nlm.nih.gov/pubmed/19836229 | https://clinicaltrials.gov/ct2/show/NCT01041443 | https://www.ncbi.nlm.nih.gov/pubmed/23397046
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2447 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19836229 |
120.0 µM [IC50] | ||
Target ID: GO:0006306 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23397046 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Synthesis and anticancer and antiviral activities of various 2'- and 3'-methylidene-substituted nucleoside analogues and crystal structure of 2'-deoxy-2'-methylidenecytidine hydrochloride. | 1991 Aug |
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Covalent DNA display as a novel tool for directed evolution of proteins in vitro. | 2004 Sep |
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Capecitabine: an evidence-based review of its effectiveness in the treatment of carcinoma of the pancreas. | 2007 Nov 30 |
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DNA mismatch repair (MMR)-dependent 5-fluorouracil cytotoxicity and the potential for new therapeutic targets. | 2009 Oct |
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Mechanistic insights on the inhibition of c5 DNA methyltransferases by zebularine. | 2010 Aug 24 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23397046
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.
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C1557
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KUA4693H5W
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515328
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C007746
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SUB33650
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DB12957
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10356-76-0
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C62785
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48006
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METABOLITE ACTIVE (PRODRUG)
SUBSTANCE RECORD