5-Azacytidine
SIGMA/A2385 - ≥98% (HPLC)
Synonym: 5-Azacitidine; 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; Ladakamycin
CAS Number: 320-67-2
Empirical Formula (Hill Notation): C8H12N4O5
Molecular Weight: 244.20
EC Number: 206-280-2
MDL Number: MFCD00006539
Linear Formula: C8H12N4O5
Product Type: Chemical
antibiotic activity spectrum | viruses |
assay | ≥98% (HPLC) |
form | powder |
InChI | 1S/C8H12N4O5/c9-7-10-2-12 |
InChI key | NMUSYJAQQFHJEW-KVTDHHQDSA |
mode of action | DNA synthesis | interferes |
mp | 226-232 °C (dec.) (lit.) |
originator | Celgene |
Quality Level | 200 |
SMILES string | NC1=NC(=O)N(C=N1)[C@@H]2O |
storage temp. | −20°C |
Application: | 5-Azacytidine has been used: • for cell induction • to study its effects on bovine fetal mesenchymal stem cells (bfMSC) • to study its effects on human bone marrow stromal cells (hBMSCs) • to study its effects on and DNA methyltransferase 1 (DNMT1) and Ras protein activator like 1 (RASAL1) expression • to interfere with DNA methylation and histone acetylation • to determine its effects on the conversion of control fibroblasts • for optical coherence tomography (OCT) and fluorescein angiography (FA) • for the reactivation of Sal-like protein (SALL)3 expression |
Biochem/physiol Actions: | 5-Azacytidine (Aza-CR) acts as a potential chemotherapeutic regimen for acute myelogenous leukemia. This drug has an ability to selectively increase γ-globin synthesis. Therefore, 5-azacytidine is used in treating severe β-thalassemia. Aza-CR acts as a potential bacteriostatic, antitumor and mutagenic agent. In addition, it also exhibits various biological activity such as, immunosuppressive, antimitotic, radioprotective and virostatic effects. |
Biochem/physiol Actions: | A potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase, an important regulatory mechanism of gene expression, gene activation and silencing. |
Biochem/physiol Actions: | Causes DNA demethylation or hemi-demethylation, creating openings that allow transcription factors to bind to DNA and reactivate tumor suppressor genes. |
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 Celgene . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here . |
General description: | 5-Azacytidine is a chemical analog of cytidine. It functions as a hypomethylating agent. 5-Azacytidine is used to treat myelodysplastic syndrome (MDS). |
General description: | Chemical structure: nucleoside |
Packaging: | 1 g in poly bottle |
Packaging: | 100, 250 mg in poly bottle |
Symbol | GHS07,GHS08,GHS09 |
Signal word | Danger |
Hazard statements | H302 - H341 - H350 - H360FD - H372 - H410 |
Precautionary statements | P202 - P260 - P264 - P273 - P301 + P312 - P308 + P313 |
Hazard Codes | T |
Risk Statements | 45-46-22 |
Safety Statements | 22-36/37/39-45 |
RIDADR | NONH for all modes of transport |
WGK Germany | WGK 3 |
Purity | ≥98% (HPLC) |
mp | 226-232 °C (dec.) (lit.) |
Storage Temp. | −20°C |
UNSPSC | 12352200 |