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2353-33-5 Usage


5-Aza-2'-deoxycytidine, also known as Decitabine, is a fine white crystalline powder that falls under the category of toxic substances. It is a potent inhibitor of DNA methylation and has been launched as a drug for the treatment of myelodysplastic syndromes (MDS), a set of hematologic disorders affecting the bone marrow. Decitabine follows the successful introduction of the first DNA methyltransferase inhibitor azacitidine and is marketed under the brand name Dacogen by Millot Laboratories, France.


Used in Oncology:
5-Aza-2'-deoxycytidine is used as a demethylating agent for the treatment of myelodysplastic syndromes (MDS), a set of hematologic disorders affecting the bone marrow that result in ineffective formation and development of blood cells. Patients with MDS have a high risk of progressing to acute myeloid leukemia (AML). Decitabine has shown to improve the quality of life and potentially modify the disease progression in these patients.
Used in Cancer Research:
5-Aza-2'-deoxycytidine is used as a demethylating agent in breast cancer cell lines, chromatin, DNA, and the promoter region of the p16 gene. It has been found to inhibit the growth of pancreatic endocrine tumor cell lines, making it a valuable tool in cancer research for understanding the epigenetic mechanisms involved in tumor growth and progression.
Used in Drug Development:
Decitabine is a potent inhibitor of DNA methylation with an IC50 of 438 nM in HL-60 cells and 4.38 nM in KG1a cells, respectively. Its ability to inhibit DNA methylation makes it a promising candidate for the development of new drugs targeting various types of cancer and other diseases related to abnormal DNA methylation patterns.

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

Neutropenia, thrombocytopenia, anemia, vomiting, fatigue, fever, cough, nausea, constipation, diarrhea, hyperglycemia, and heat induced neutrophil. Large doses may cause neurotoxicity, manifested as lethargy, aphasia, hemiplegia, etc., which disappears after stopping.

Toxicity grading


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.


Pharmachemie (Netherlands)

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.

Biochem/physiol Actions

Primary TargetDNA methyltransferase inhibitor

Clinical Use

Antineoplastic antimetabolite agent:Treatment of acute myeloid leukaemia

Safety Profile

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


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.

Drug interactions

Potentially hazardous interactions with other drugsAntipsychotics: avoid with clozapine, increased risk of agranulocytosis.


The exact route of metabolism and elimination is unknown but thought to be through deamination by cytidine deaminase in the liver, kidney, intestinal epithelium and blood to form inactive metabolites.


1) Bender et al. (1998), Inhibition of DNA methylation by 5-aza-2′-deoxycytidine suppresses the growth of human tumor cell lines; Cancer Res., 58 95 2) El-Serafi et al. (2011), Epigenetic modifiers influence lineage commitment of human bone marrow stromal cells: Differential effects of 5-aza-deoxycytidine and trichostatin A; Differentiation, 81 35

Check Digit Verification of cas no

The CAS Registry Mumber 2353-33-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,5 and 3 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2353-33:
65 % 10 = 5
So 2353-33-5 is a valid CAS Registry Number.

2353-33-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (A2232)  5-Aza-2'-deoxycytidine  

  • 2353-33-5

  • 20mg

  • 700.00CNY

  • Detail
  • TCI America

  • (A2232)  5-Aza-2'-deoxycytidine  

  • 2353-33-5

  • 100mg

  • 1,990.00CNY

  • Detail
  • Sigma

  • (A3656)  5-Aza-2′-deoxycytidine  ≥97%

  • 2353-33-5

  • A3656-5MG

  • 983.97CNY

  • Detail
  • Sigma

  • (A3656)  5-Aza-2′-deoxycytidine  ≥97%

  • 2353-33-5

  • A3656-10MG

  • 1,702.35CNY

  • Detail
  • Sigma

  • (A3656)  5-Aza-2′-deoxycytidine  ≥97%

  • 2353-33-5

  • A3656-50MG

  • 5,879.25CNY

  • Detail



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017


1.1 GHS Product identifier

Product name 5-aza-2'-deoxycytidine

1.2 Other means of identification

Product number -
Other names DECITABINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2353-33-5 SDS

2353-33-5Relevant articles and documents

Decitabine intermediate compound VI


Paragraph 0055; 0124-0132, (2021/01/24)

The invention belongs to the technical field of chemical synthesis, and provides a decitabine intermediate compound. A preparation route of the decitabine intermediate compound comprises the followingsteps: taking an oxymethyl compound of a hydroxyl group at a 1 site of 2-deoxy-D-ribose as a raw material, protecting a hydroxyl group at a 3 site and a hydroxyl group at a 5 site respectively, then performing acetylation substitution on a 1 site of sugar, and further treating to obtain the compound. The method is simple and convenient to operate, does not need special equipment, is good in product purity and high in yield, and is suitable for industrial production; decitabine is further synthesized by utilizing the compound, so that the stereoselectivity is high, and the purity isgood.

Preparation method of decitabine


Paragraph 0010; 0035-0036; 0038-0039; 0041-0042; 0044-0045, (2021/01/15)

The invention belongs to the technical field of organic synthesis, and provides a preparation method of decitabine. The preparation method specifically comprises the following steps: first carrying out reflux extraction to obtain a mixture of decitabine alpha and beta isomers, and then separating the isomers by applying the supercritical fluid technology to obtain high-purity decitabine. Comparedwith the prior art, the technical method which is simple in operation process, high in separation efficiency, high in product yield, high in final product purity and suitable for industrial productionis provided.

Synthetic method of decitabine


Paragraph 0052; 0053, (2019/08/01)

The present invention relates to a synthetic method of decitabine, and discloses a method for synthesizing a compound as shown in a formula I, The method comprises the steps of: reacting a compound IIwith a compound III by a following reaction in a solvent under the action of TMSOTf to obtain a compound I. The synthetic method of the invention has the advantages that the raw materials are easy toobtain, the operation is safe, the conditions are mild and easy to control, and a solid product obtained by an acylation protection is easy to be crystallized and purified, which is favorable for thenext reaction and improves the selectivity of a final beta-isomer product, no further conversion to hydroxymethyl is required, the reaction step is simplified, the reaction yield of each step is good, the atomic economy is high, and the method is suitable for a large number of industrial production and the like.

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