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
| Molecular Formula | C9H12FN3O4 |
| Molecular Weight | 245.2077 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator'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
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 |
120.0 µM [IC50] | ||
Target ID: GO:0006306 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3302 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25567350/ |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: TETRAHYDROURIDINE |
5-FLUORO-2'-DEOXYCYTIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4107 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26321472 |
100 mg/m² single, oral dose: 100 mg/m² route of administration: Oral experiment type: SINGLE co-administered: TETRAHYDROURIDINE |
5-FLUORO-2'-DEOXYCYTIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
693 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25567350/ |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: TETRAHYDROURIDINE |
5-FLUORO-2'-DEOXYCYTIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
912 μg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26321472 |
100 mg/m² single, oral dose: 100 mg/m² route of administration: Oral experiment type: SINGLE co-administered: TETRAHYDROURIDINE |
5-FLUORO-2'-DEOXYCYTIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
46.5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25567350/ |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: TETRAHYDROURIDINE |
5-FLUORO-2'-DEOXYCYTIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Mechanistic insights on the inhibition of c5 DNA methyltransferases by zebularine. | 2010-08-24 |
|
| DNA mismatch repair (MMR)-dependent 5-fluorouracil cytotoxicity and the potential for new therapeutic targets. | 2009-10 |
|
| Capecitabine: an evidence-based review of its effectiveness in the treatment of carcinoma of the pancreas. | 2007-11-30 |
|
| Covalent DNA display as a novel tool for directed evolution of proteins in vitro. | 2004-09 |
|
| Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases. | 2002-08-23 |
|
| Synthesis and anticancer and antiviral activities of various 2'- and 3'-methylidene-substituted nucleoside analogues and crystal structure of 2'-deoxy-2'-methylidenecytidine hydrochloride. | 1991-08 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:14:53 GMT 2025
by
admin
on
Mon Mar 31 18:14:53 GMT 2025
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| Record UNII |
KUA4693H5W
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
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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|---|---|---|---|---|
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METABOLITE ACTIVE -> PRODRUG |
