2'-Deoxy-5-fluorcytidine

Modify Date: 2024-01-02 17:55:56

2'-Deoxy-5-fluorcytidine Structure
2'-Deoxy-5-fluorcytidine structure
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
GHS07
Signal Word Warning

 Use of 2'-Deoxy-5-fluorcytidine


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].

 Names

Name 2'-Deoxy-5-fluorocytidine
Synonym More Synonyms

 2'-Deoxy-5-fluorcytidine Biological Activity

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
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
Storage condition room temp

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HA3850000
CHEMICAL NAME :
Cytidine, 2'-deoxy-5-fluoro-
CAS REGISTRY NUMBER :
10356-76-0
LAST UPDATED :
199709
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C9-H12-F-N3-O4
MOLECULAR WEIGHT :
245.24
WISWESSER LINE NOTATION :
T6N CNJ DZ EF F- BT5OTJ EO1

HEALTH HAZARD DATA

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

 Safety Information

Symbol GHS07
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

 Synthetic Route

~67%

2'-Deoxy-5-fluorcytidine Structure

2'-Deoxy-5-fluo...

CAS#:10356-76-0

Literature: Yamaguchi; Saneyoshi Chemical and Pharmaceutical Bulletin, 1984 , vol. 32, # 4 p. 1441 - 1450

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2'-Deoxy-5-fluorcytidine Structure

2'-Deoxy-5-fluo...

CAS#:10356-76-0

Literature: Journal of Organic Chemistry, , vol. 57, # 11 p. 2989 - 2991

~%

2'-Deoxy-5-fluorcytidine Structure

2'-Deoxy-5-fluo...

CAS#:10356-76-0

Literature: Journal of Organic Chemistry, , vol. 57, # 11 p. 2989 - 2991

~%

2'-Deoxy-5-fluorcytidine Structure

2'-Deoxy-5-fluo...

CAS#:10356-76-0

Literature: Journal of Organic Chemistry, , vol. 57, # 11 p. 2989 - 2991

~%

2'-Deoxy-5-fluorcytidine Structure

2'-Deoxy-5-fluo...

CAS#:10356-76-0

Literature: Chemical and Pharmaceutical Bulletin, , vol. 32, # 4 p. 1441 - 1450

 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
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