5-Aza-2′-deoxycytidine
SIGMA/A3656 - ≥97%
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
EC Number: 219-089-4
MDL Number: MFCD00043011
Linear Formula: C8H12N4O4
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A3656-10MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A3656-5MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A3656-50MG
| assay | ≥97% |
| form | powder |
| InChI | 1S/C8H12N4O4/c9-7-10-3-12 |
| InChI key | XAUDJQYHKZQPEU-KVQBGUIXSA |
| originator | Eisai |
| Quality Level | 200  |
| SMILES string | NC1=NC(=O)N(C=N1)[C@H]2C[ |
| solubility | acetic acid: water (1:1): 50 mg/mL |
| Application: | 5-Aza-2′-deoxycytidine has been used as a demethylating agent in breast cancer cell line, chromatin, DNA and promoter region of p16 gene. |
| 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 . |
| Features and Benefits: | This compound was developed by Eisai . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here . |
| General description: | 5-Aza-2′-deoxycytidine, also known as Decitabine, is a DNA-hypomethylating agent that promotes differentiation and apoptosis in leukemic cells. It is a 2′-deoxycytidine analog that causes DNA demethylation or hemi-demethylation, which can regulate gene expression by "opening" the chromatin structure, making it more sensitive to nucleases. This chromatin remodeling allows transcription factors to bind to promoter regions, facilitating the assembly of the transcription complex and subsequent gene expression. As an epigenetic modifier, Decitabine inhibits DNA methyltransferase activity, leading to DNA hypomethylation and gene activation. The reactivation of genes is further enhanced when demethylation is combined with histone hyperacetylation. Decitabine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome, and acute myeloid leukemia. |
| 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. |
| Packaging: | 5, 10 mg in glass bottle |
| Packaging: | 50 mg in glass insert |
| Preparation Note: | When prepared properly, there may be a small amount of undissolved substance. |
| Symbol |   GHS07,GHS08 |
| Signal word | Danger |
| Hazard statements | H302 - H315 - H319 - H335 - H341 - H360 |
| Precautionary statements | P201 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 - P308 + P313 |
| Hazard Codes | T |
| Risk Statements | 61-22-36/37/38-68 |
| Safety Statements | 26-36/37 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Purity | ≥97% |
| UNSPSC | 12352200 |