A2385

5-Azacytidine

≥98% (HPLC)

• Synonym(s): 5-Azacitidine, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin
• Empirical Formula (Hill Notation): C₈H₁₂N₄O₅
• CAS Number: 320-67-2
• Molecular Weight: 244.20
• Beilstein: 620461
• EC Number: 206-280-2
• MDL number: MFCD00006539
• PubChem Substance ID: 24278211
• NACRES: NA.77

Properties

• Quality Level: 200
• assay: ≥98% (HPLC)
• form: powder
• mp: 226-232 °C (dec.) (lit.)
• antibiotic activity spectrum: viruses
• Mode of action: DNA synthesis | interferes
• originator: Celgene
• storage temp.: −20°C
• SMILES string: NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
• InChI: 1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
• InChI key: NMUSYJAQQFHJEW-KVTDHHQDSA-N
• Gene Information: human ... DNMT1(1786) , DNMT3A(1788) , DNMT3B(1789)

Description

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).

Chemical structure: nucleoside

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

Packaging

100, 250 mg in poly bottle

1 g in poly bottle

Biochem/physiol Actions

A potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase, an important regulatory mechanism of gene expression, gene activation and silencing.

Causes DNA demethylation or hemi-demethylation, creating openings that allow transcription factors to bind to DNA and reactivate tumor suppressor genes.

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.

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.

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.

Safety Information

• Pictograms: 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 Classifications: Acute Tox. 4 Oral - Aquatic Chronic 1 - Carc. 1A - Muta. 2 - Repr. 1B - STOT RE 1
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves