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5-Aza-2'-deoxycytidine

Indications and Usage Mechanisms of Action Side Effects Category Toxicity grading Acute toxicity Flammability Hazardous characteristics Storage characteristics Fire extinguishing agent
5-Aza-2'-deoxycytidine
5-Aza-2'-deoxycytidine structure
CAS No.
2353-33-5
Chemical Name:
5-Aza-2'-deoxycytidine
Synonyms
Dacogen;CS-1979;5-AZA-DC;5-AZA-CDR;Decitabin;NSC 127716;DECITABINE;5-Aza-2'Aza deoxycytidine;5-azadeoxycytidine
CBNumber:
CB6284800
Molecular Formula:
C8H12N4O4
Formula Weight:
228.21
MOL File:
2353-33-5.mol

5-Aza-2'-deoxycytidine Properties

Melting point:
~200 °C (dec.)
alpha 
D22 +68.5° (30 min) +57.8° (6 hr) (c = 0.5 in water)
Boiling point:
370.01°C (rough estimate)
Density 
1.3771 (rough estimate)
refractive index 
1.6590 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
acetic acid/water (1:1): 50 mg/mL
form 
Powder
pka
14.02±0.60(Predicted)
color 
White to Off-white
Merck 
14,2853
BRN 
617982
Stability:
Stable. May be light or air sensitive. Incompatible with strong oxidizing agents.
InChIKey
XAUDJQYHKZQPEU-KVQBGUIXSA-N
CAS DataBase Reference
2353-33-5(CAS DataBase Reference)
FDA UNII
776B62CQ27
NCI Dictionary of Cancer Terms
Dacogen; decitabine
NCI Drug Dictionary
Dacogen
ATC code
L01BC08
EPA Substance Registry System
5-Aza-2'-deoxycytidine (2353-33-5)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H315-H319-H335-H341-H360
Precautionary statements  P202-P280-P405-P501-P201-P261-P281-P305+P351+P338-P308+P313-P501a
Hazard Codes  Xn,Xi,T
Risk Statements  22-36/37/38-68-61
Safety Statements  26-36-36/37
WGK Germany  3
RTECS  XZ3012000
10-34
HS Code  29349990
Toxicity LD50 in mice (mg/kg): 190 i.p. (Momparler, 1985)

5-Aza-2'-deoxycytidine price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A3656 5-Aza-2′-deoxycytidine ≥97% 2353-33-5 5mg $81.6 2021-03-22 Buy
Sigma-Aldrich 189826 InSolution? 5-Aza-2?-Deoxycytidine 2353-33-5 10mg $129 2021-03-22 Buy
TCI Chemical A2232 5-Aza-2'-deoxycytidine 2353-33-5 20mg $66 2021-03-22 Buy
TCI Chemical A2232 5-Aza-2'-deoxycytidine 2353-33-5 100mg $227 2021-03-22 Buy
Alfa Aesar J65513 5-Aza-2'-deoxycytidine, 98% 2353-33-5 100mg $237 2021-03-22 Buy

5-Aza-2'-deoxycytidine Chemical Properties,Uses,Production

Indications and Usage

5-Aza-2’-deoxycytidine, also known as decitabine or 2'-deoxy-5-azacytidine, is a cell cycle S phase-specific drug used to treat myelodysplastic syndromes (MDS.)

Mechanisms of Action

Demethylating agents can regulate gene expression by activating tumor suppressor genes and enhancing the differentiation of genes, which help treat MDS. 5-Aza-2’-deoxycytidine is a natural andenosine analogue of 2′-deoxycytidine, known to the be strongest methylation specific inhibitor of DNA. After phosphorylation it can inhibit DNA methyltransferase, reducing DNA methylation, leading to demethylation of tumor cells, which can restore the normal functioning of genes, thus inhibiting tumor cell proliferation and preventing the occurrence of drug resistance. 5-Aza-2’-deoxycytidine inhibits DNA methylation in vitro, but does not affect its synthesis. Moreover, non-proliferating cells are not sensitive to it. 5-Aza-2’-deoxycytidine has anti-tumor activity and is characterized by a dual mechanism based on dose differences. At high concentrations it is cytoxic, while at low concentrations it is demethlyating.

Side Effects

Category

toxic substance

Toxicity grading

high

Acute toxicity

Intravenous – mouse LD50: 22 mg/kg; peritoneal – mouse LD50: 190 mg/kg

Flammability Hazardous characteristics

Combustible; produces toxic nitrogen oxide fumes.

Storage characteristics

Ventilated, cold, and dry; store away from raw food materials.

Fire extinguishing agent

dry powder, foam, sand, carbon dioxide, water mist.

Description

Decitabine, 5-aza-2’-deoxycytidine, has been launched for the treatment of myelodysplastic syndromes (MDS). MDS are a set of hematologic disorders affecting the bone marrow that result in ineffective formation and development of blood cells. Furthermore, patients with MDS have a high risk of progressing to acute myeloid leukemia (AML). Traditional treatments include blood transfusions, hematopoietic growth factors, and prophylactic antibiotics, but these measures merely improve the quality of life with questionable effects on disease modification. While stem-cell transplantation is an aggressive, potentially curative approach, the advanced age or the other complicating health issues of most patients preclude them from considering this option. Recent advances in the underlying etiology of MDS, however, have led to the development of a new class of compounds known as ‘‘demethylating agents’’. Decitabine follows the successful introduction of the first DNA methyltransferase inhibitor azacitidine.

Chemical Properties

white crystalline powder

Originator

Pharmachemie (Netherlands)

Uses

Used as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines.

Uses

Decitabine is a potent inhibitor of DNA methylation with IC50 of 438 nM and 4.38 nM in HL-60 and KG1a cells, respectively

brand name

Dacogen (Millot Laboratories, France).

General Description

Fine white crystalline powder. Used as a drug.

Air & Water Reactions

Probably light and air sensitive. Water soluble. Decomposes in aqueous solution at a rate that depends on pH: at pH 7 the drug is more stable than at pH 9, but is less stable than at pH 6. At pH 7 and 99°F, approximately 7% conversion occurs in 1 hour .

Reactivity Profile

5-Aza-2'-deoxycytidine is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data for 5-Aza-2'-deoxycytidine are not available. 5-Aza-2'-deoxycytidine is probably combustible.

Biological Activity

Cytosine analog that once incorporated into DNA acts as a suicide substrate for DNA methyltransferase. Inhibits DNA methyltransferase and results in DNA hypomethylation and activation of silent genes. Chemotherapeutic agent; suppresses growth of human tumor cell lines. Demethylates differentiation-related genes; reverses embryonic stem cell differentiation.

Safety Profile

Poison by intravenous route.Human mutation data reported. When heated todecomposition it emits toxic fumes of NOx.

Chemical Synthesis

Silylated 5-aza-cytosine (28) was condensed with 9- fluorenylmethoxycarbonyl (Fmoc) protected 2-deoxy-1-chlororibose (27) with tin chloride (IV) in dichloroethane (Scheme 4). The coupled product 29 was de-protected with excess triethylamine in dry pyridine to give decitabine (IV) in 36% yield after separation from its corresponding αisomer.

5-Aza-2'-deoxycytidine Preparation Products And Raw materials

Raw materials

Preparation Products


5-Aza-2'-deoxycytidine Suppliers

Global( 476)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Beijing Ribio Biotech Co.,Ltd
010-62664360
wucy@ribio.com.cn CHINA 117 58
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20012 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 20898 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8909 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
02783214688 bruce@xrdchem.cn CHINA 567 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26762 60
Lianyungang happen teng technology co., LTD
15950718863
wang666xt@163.com CHINA 296 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58

View Lastest Price from 5-Aza-2'-deoxycytidine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-08 5-Aza-2'-deoxycytidine
2353-33-5
US $10.00 / KG 1KG 99.9% 100MT/Month Wuhan wingroup Pharmaceutical Co., Ltd
2021-10-22 Decitabine
2353-33-5
US $0.00 / KG 10g 98%min 10kg WUHAN FORTUNA CHEMICAL CO., LTD
2021-07-13 Decitabine
2353-33-5
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

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