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  • A3656 - 5-Aza-2′-deoxycytidine

A3656 Sigma-Aldrich



Synonym: 2′-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Decitabine

  • CAS Number 2353-33-5

  • Empirical Formula (Hill Notation) C8H12N4O4

  • Molecular Weight 228.21

  •  Beilstein/REAXYS Number 617982

  •  EC Number 219-089-4

  •  MDL number MFCD00043011

  •  PubChem Substance ID 24890797

  •  NACRES NA.77



Related Categories AN-AZ, Antitumor Agents, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   200
assay   ≥97%
solubility   acetic acid: water (1:1): 50 mg/mL
originator   Eisai
SMILES string   NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2
InChI   1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
Gene Information   human ... DNMT1(1786), DNMT3A(1788)


General description

5-Aza-2′-deoxycytidine is a DNA-hypomethylating agent, which stimulates differentiation and apoptosis of leukemic cells. It is a 2′-deoxycytidine analogue. 5-Aza-2′-deoxycytidine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome and acute myeloid leukemia.


5-Aza-2′-deoxycytidine has been used as a demethylating agent in breast cancer cell line, chromatin, DNA and promoter region of p16 gene.


5, 10 mg in glass bottle

50 mg in glass insert

Biochem/physiol Actions

5′-Azadeoxycytidine causes DNA demethylation or hemi-demethylation. DNA demethylation can regulate gene expression by "opening" the chromatin structure detectable as increased nuclease sensitivity. This remodeling of chromatin structure allows transcription factors to bind to the promoter regions, assembly of the transcription complex, and gene expression. Decitabine is an epigenetic modifier that inhibits DNA methyltransferase activity which results in DNA demethylation (hypomethylation) and gene activation by remodeling "opening" chromatin. Genes are synergistically reactivated when demethylation is combined with histone hyperacetylation.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Eisai. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety & Documentation

Safety Information

Signal word 
Target organs 
Respiratory system
Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How should Product A3656, 5-Aza-2´-deoxycytidine, be dissolved?
This product is typically dissolved at 50 mg/ml in 50% acetic acid to yield a clear colorless solution. This product is also soluble at 50 mg/ml in DMSO or 0.25 mg/ml in water.
What is the solution stability of Product A3656, 5-Aza-2´-deoxycytidine?
Aqueous solutions of this product appear to be very unstable, probably by analogy to A2385, aza-cytidine. We suggest preparing solution fresh for each use and storing solutions on ice until use within a few hours.
What is the difference between 5-Aza-2´-deoxycytidine Products A3656 and A1287?
Both of these products inhibit DNA methyltransferase.However, they are different chemicals.Product No. A3656 is 5-Aza-2´-deoxycytidine and A1287 is 5-Azacytidine. Product No. A1287 is γ-irradiated, hybridoma- and endotoxin-tested, and Product No. A3656 is not.
How do I find price and availability?
There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 or view local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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Protocols & Articles


Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete. The expansion of the carcinogenesi...
Vicki Caligur
BioFiles 2008, 3.5, 18.
Keywords: Acetylations, Adhesion, Alkylations, Apoptosis, Biofiles, Cancer, Carcinogens, Cell division, Cell proliferation, Cell signaling, DNA microarrays, Drug discovery, Environmental, Epigenetics, Events, Gene expression, Genetic, Hormones, Metabolism, Methylations, Microarray Analysis, Mutagens, PAGE, Recombination, Reductions, Sequences, Transcription, Type, transformation

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

Modulators and Proteins for Methylation

DNA methyltransferases are a family of enzymes that catalyze the transfer of a methyl group to DNA. There are five related DNA cytosine-5-methyltransferases (DNMTs) that transfer a methyl group from ...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 7–9
Keywords: Gene expression, Methylations

Peer-Reviewed Papers


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