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10356-76-0

10356-76-0 structure
10356-76-0 structure
  • Name: 2'-Deoxy-5-fluorcytidine
  • Chemical Name: 2'-Deoxy-5-fluorocytidine
  • CAS Number: 10356-76-0
  • Molecular Formula: C9H12FN3O4
  • Molecular Weight: 245.208
  • Catalog: Signaling Pathways Epigenetics DNA Methyltransferase
  • Create Date: 2018-09-03 16:59:34
  • Modify Date: 2024-01-02 17:55:56
  • 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].
Name 2'-Deoxy-5-fluorocytidine
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
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.
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

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
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
92574-68-0 structure

92574-68-0

~67%

10356-76-0 structure

10356-76-0

Literature: Yamaguchi; Saneyoshi Chemical and Pharmaceutical Bulletin, 1984 , vol. 32, # 4 p. 1441 - 1450
161179-94-8 structure

161179-94-8

~%

10356-76-0 structure

10356-76-0

Literature: Journal of Organic Chemistry, , vol. 57, # 11 p. 2989 - 2991
110522-47-9 structure

110522-47-9

~%

10356-76-0 structure

10356-76-0

Literature: Journal of Organic Chemistry, , vol. 57, # 11 p. 2989 - 2991
50-91-9 structure

50-91-9

~%

10356-76-0 structure

10356-76-0

Literature: Journal of Organic Chemistry, , vol. 57, # 11 p. 2989 - 2991
51255-12-0 structure

51255-12-0

~%

10356-76-0 structure

10356-76-0

Literature: Chemical and Pharmaceutical Bulletin, , vol. 32, # 4 p. 1441 - 1450
Precursor  3

DownStream  0

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
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