CAS 10356-76-0|2'-Deoxy-5-fluorcytidine
| Common Name | 2'-Deoxy-5-fluorcytidine | ||
|---|---|---|---|
| CAS Number | 10356-76-0 | Molecular Weight | 245.208 |
| Density | 1.8±0.1 g/cm3 | Boiling Point | 465.0±55.0 °C at 760 mmHg |
| Molecular Formula | C9H12FN3O4 | Melting Point | 196 °C |
| MSDS | USA | Flash Point | 235.0±31.5 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | 2'-Deoxy-5-fluorocytidine |
|---|---|
| Synonym | More Synonyms |
2'-Deoxy-5-fluorcytidine BiologicalActivity
| Description | 5-Fluoro-2'-deoxycytidine, a fluoropyrimidine nucleoside analogue, is a DNA methyltransferase (DNMT) inhibitor. 5-Fluoro-2'-deoxycytidine is a tumor-selective prodrug of the potent thymidylate synthase inhibitor 5-fluoro-2′-dUMP[1][2]. |
|---|---|
| Related Catalog | Research Areas >>CancerSignaling Pathways >>Epigenetics >>DNA Methyltransferase |
| Target | DNA methyltransferase (DNMT)[1] |
| References | [1]. Beumer JH, et, al. Pharmacokinetics, metabolism, and oral bioavailability of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine in mice. Clin Cancer Res. 2006 Dec 15;12(24):7483-91. [2]. Osterman DG, et, al. 5-Fluorocytosine in DNA is a mechanism-based inhibitor of HhaI methylase. Biochemistry. 1988 Jul 12;27(14):5204-10. |
Chemical & Physical Properties
| Density | 1.8±0.1 g/cm3 |
|---|---|
| Boiling Point | 465.0±55.0 °C at 760 mmHg |
| Melting Point | 196 °C |
| Molecular Formula | C9H12FN3O4 |
| Molecular Weight | 245.208 |
| Flash Point | 235.0±31.5 °C |
| Exact Mass | 245.081177 |
| PSA | 110.60000 |
| LogP | -1.61 |
| Vapour Pressure | 0.0±2.6 mmHg at 25°C |
| Index of Refraction | 1.697 |
| InChIKey | IDYKCXHJJGMAEV-RRKCRQDMSA-N |
| SMILES | Nc1nc(=O)n(C2CC(O)C(CO)O2)cc1F |
| Storage condition | room temp |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 20 mg/kg
- SEX/DURATION :
- female 15-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 156 ug/kg
- SEX/DURATION :
- female 8 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 6200 ug/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 1500 ug/kg
- SEX/DURATION :
- female 10 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 312 ug/kg
- SEX/DURATION :
- female 8 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 10 mg/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - other effects to embryo
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- DOSE :
- 10 mg/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - hepatobiliary system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 2500 ug/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - urogenital system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 5 mg/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 1250 ug/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - eye/ear
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 156 ug/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
MUTATION DATA - TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 10 umol/L
- REFERENCE :
- CHROAU Chromosoma. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1939- Volume(issue)/page/year: 85,603,1982 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965
- TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 10 umol/L
- REFERENCE :
- CHROAU Chromosoma. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1939- Volume(issue)/page/year: 85,603,1982 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302 |
| Hazard Codes | Xn |
| Risk Phrases | 22 |
| RIDADR | NONH for all modes of transport |
| RTECS | HA3850000 |
| HS Code | 2934999090 |
Customs
| HS Code | 2934999090 |
|---|---|
| Summary | 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles24
More Articles| Concentrations of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd) and its cytotoxic metabolites in plasma of patients treated with FdCyd and tetrahydrouridine (THU). Cancer Chemother. Pharmacol. 62(2) , 363-8, (2008) Although the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd), is being evaluated clinically, it must be combined with the cytidine deaminase inhibitor tetrahydrouridine (THU) to prev... | |
| Five-chlorodeoxycytidine and biomodulators of its metabolism result in fifty to eighty percent cures of advanced EMT-6 tumors when used with fractionated radiation. Int. J. Radiat. Oncol. Biol. Phys. 32(4) , 1059-69, (1995) To extend our findings in previous radiation and biochemical studies with five rodent tumors, in which we used one and occasionally two or three irradiations. The extent of control of the EMT-6 mammar... | |
| Chemical synthesis of 2'-deoxyoligonucleotides containing 5-fluoro-2'-deoxycytidine. Nucleic Acids Res. 20(10) , 2421-6, (1992) 2'-Deoxyoligonucleotides with 5-fluorocytosine residues incorporated at specific positions of the nucleotide sequence are tools of great potential in the study of the catalytic mechanism by which DNA ... |
Synonyms
| 5-Fluoro-2′-deoxycytidine |
| 2'-Deoxy-5-fluorcytidine |
| 4-Amino-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone |
| 5-Fluorodeoxycytidine |
| 2(1H)-pyrimidinone, 4-amino-1-(2-deoxy-β-D-glycero-pentofuranosyl)-5-fluoro- |
| Cytidine, 2'-deoxy-5-fluoro- |
| 4-Amino-1-(2-deoxy-β-D-glycero-pentofuranosyl)-5-fluoropyrimidin-2(1H)-one |
| MFCD00077348 |
| 2'-Deoxy-5-fluorocytidine |
| 5-Fluoro-2'-deoxycytidine |
| 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-fluorpyrimidin-2(1H)-on |
