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2'-DEOXY-5-FLUOROCYTIDINE

Product Name
2'-DEOXY-5-FLUOROCYTIDINE
CAS No.
10356-76-0
Chemical Name
2'-DEOXY-5-FLUOROCYTIDINE
Synonyms
FCDR;FdCyd;5--F-dC;NSC 48006;Ro 5-1090;5-F-2'-dC;5-Fluoro-2;5-F-2'-deoxycytidine;5-fluorodeoxycytidine;5-fluor-desoxycytidin
CBNumber
CB1122369
Molecular Formula
C9H12FN3O4
Formula Weight
245.21
MOL File
10356-76-0.mol
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2'-DEOXY-5-FLUOROCYTIDINE Property

Melting point:
196 °C
Boiling point:
465℃
Density 
1.82
refractive index 
70 ° (C=1, H2O)
Flash point:
235℃
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
DMSO: >20mg/mL
form 
powder
pka
14.03±0.60(Predicted)
color 
white to off-white
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
CAS DataBase Reference
10356-76-0(CAS DataBase Reference)
EPA Substance Registry System
5-Fluoro-2'-deoxycytidine (10356-76-0)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
HA3850000
HS Code 
2940.00.6000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
F5307
Product name
5?Fluoro?2′?deoxycytidine
Purity
≥98% (HPLC), powder
Packaging
5mg
Price
$43.2
Updated
2024/03/01
Sigma-Aldrich
Product number
F5307
Product name
5?Fluoro?2′?deoxycytidine
Purity
≥98% (HPLC), powder
Packaging
25mg
Price
$419
Updated
2024/03/01
TCI Chemical
Product number
D3642
Product name
2'-Deoxy-5-fluorocytidine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$274
Updated
2024/03/01
TCI Chemical
Product number
D3642
Product name
2'-Deoxy-5-fluorocytidine
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$822
Updated
2023/06/20
TRC
Product number
F590803
Product name
5-Fluoro-2''-deoxycytidine
Packaging
5mg
Price
$60
Updated
2021/12/16
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2'-DEOXY-5-FLUOROCYTIDINE Chemical Properties,Usage,Production

Description

5-Fluoro-2-Deoxycytidine is an antimetabolite consisting of a fluorinated pyrimidine analog 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. This inhibits DNA synthesis and cell division. FUTP competes with uridine triphosphate for incorporation into the RNA strand thus leading to an inhibition of RNA and protein synthesis. Other fluorouracil metabolites also get incorporated into both DNA and RNA, thereby further hampering cellular growth.

Uses

5-Fluoro-2''-deoxycytidine is a mechanism-based DNMT inhibitor.

Uses

5-fluoro-2'-deoxycytidine has been used in trials studying the treatment of Neoplasms, Lung Neoplasms, Breast Neoplasms, Head and Neck Neoplasms, and Urinary Bladder Neoplasms, among others.

General Description

Fine white powder.

Air & Water Reactions

2'-DEOXY-5-FLUOROCYTIDINE is probably light and air sensitive.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2'-DEOXY-5-FLUOROCYTIDINE emits toxic fumes of fluoride ion and NOx.

Fire Hazard

Flash point data for 2'-DEOXY-5-FLUOROCYTIDINE are not available. 2'-DEOXY-5-FLUOROCYTIDINE is probably combustible.

Pharmacology

5-Fluoro-2'-deoxycytidine (FdCyd), a fluoropyrimidine nucleoside analog, has a short (10-minute) half-life and is rapidly degraded in vivo by cytidine deaminase. However, coadministration with tetrahydrouridine (THU), an inhibitor of cytidine/deoxycytidine deaminase, has been shown to increase the AUC of the parent compound more than 4-fold. Increased FdCyd exposure allows it to be taken up intracellularly and converted to its triphosphate, which is incorporated into DNA and inhibits the action of the enzyme DNA methyltransferase (DNMT). Inhibition of DNMT, and in turn DNA methylation, can result in the re-expression of tumor suppressor genes.
Primary objective:
-Determine progression-free survival (PFS) and/or the response rate (CR + PR) of FdCyd administered 5 days per week for 2 weeks, in 28-day cycles, by intravenous infusion over 3 hours along with THU in patients with breast cancer, head and neck cancer, non-small cell lung cancer, and urothelial transitional cell carcinoma.
Exploratory objectives:
Evaluate whether treatment with FdCyd and THU alters DNA methylation patterns in tumor biopsy samples before and during treatment by LINE-1 analysis.
Evaluate the safety and tolerability of FdCyd (100 mg/m(2)) + THU (350 mg/m(2)) administered 5 days per week for 2 weeks, in 28-day cycles, by intravenous infusion over 3 hours.
Measure changes in the number of CTCs following treatment with FdCyd plus THU.

Clinical Use

A DNA methyltransferase inhibitor currently in clinical trials for breast cancer and other solid tumors. Like 5’-Azacytidine and decitabine, 2’-Deoxy-5-fluorocytidine is a pyrimidine analog that integrates into chromatin to inhibit DNA methylation. It blocks proliferation in colon cancer-derived HCT116 cells by activating DNA response pathways. It inhibits various strains of pathogenic avian influenza viruses in vitro and in vivo.

References

1) Ren?et al. (2011),?DNA hypermethylation as a chemotherapy target; Cell Signal,?23?1082 2) Gowher?et al. (2004),?Mechanism of inhibition of DNA methyltransferases by cytidine analogs in cancer therapy; Cancer Biol. Ther.,?3?1062 3) Zhao?et al. (2002),?Inhibition of cancer cell proliferation by 5-fluoro-2′-deoxycytidine, a DNA methylation inhibitor, through activation of DNA damage response pathway; Springerplus,?1?65 4) Kumaki?et al. (2001),?In vitro and in vivo efficacy of fluorodeoxycytidine analogs against highly pathogenic avian influenza H5N1, seasonal, and pandemic H1N1 virus infections; Antiviral Res.,?92?329

2'-DEOXY-5-FLUOROCYTIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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2'-DEOXY-5-FLUOROCYTIDINE Suppliers

CHEMOS GmbH & Co. KG
Tel
--
Fax
--
Email
chemos@chemos.de
Country
Germany
ProdList
6727
Advantage
58
Service Chemical Inc.
Tel
--
Fax
--
Email
sales@chemos-group.com
Country
Germany
ProdList
6350
Advantage
71
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View Lastest Price from 2'-DEOXY-5-FLUOROCYTIDINE manufacturers

Xinxiang Aurora Biotechnology Co.,Ltd.
Product
2'-DEOXY-5-FLUOROCYTIDINE 10356-76-0
Price
US $0.00/Kg
Min. Order
1Kg
Purity
98%
Supply Ability
20Ton
Release date
2024-10-16
Hebei Weibang Biotechnology Co., Ltd
Product
2'-Deoxy-5-fluorocytidine 10356-76-0
Price
US $30.00-10.00/KG
Min. Order
50KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-05
Hebei Yanxi Chemical Co., Ltd.
Product
2'-Deoxy-5-fluorocytidine 10356-76-0
Price
US $30.00-10.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-10-19

10356-76-0, 2'-DEOXY-5-FLUOROCYTIDINERelated Search:


  • 2'-DEOXY-5-FLUOROCYTIDINE
  • 2’-deoxy-5-fluoro-cytidin
  • 5-FLUORO-2'-DEOXYCYTIDINE
  • 5-fluor-desoxycytidin
  • 5-fluorodeoxycytidine
  • 5--F-dC
  • 2′-deoxy-5-fluoroCytidine\5-Fluoro-2′-deoxycytidine
  • 4-AMino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidin-2(1H)-one
  • Cytidine,2'-deoxy-5-fluoro-
  • FCDR
  • FdCyd
  • 5-F-2'-deoxycytidine
  • 5-Fluoro-2
  • NSC 48006
  • Ro 5-1090
  • 5-F-2'-dC
  • 2'-Deoxy-5-fluorocytidine&gt
  • -Deoxy-5-fluorocytidine
  • 5-Fluoro-2'-deoxycytidine
  • 2'-Deoxy-5-fluorocytidine
  • 10356-76-0
  • Biochemistry
  • Nucleosides and their analogs
  • Nucleosides, Nucleotides & Related Reagents
  • Nucleosides-5-F Nucleosides