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

Catalog Number	PKG Qty.	Price


45-A2385-100MG	100 mg	$67.40 1/EA	Add To Favorites
45-A2385-250MG	250 mg	$142.00 1/EA	Add To Favorites
45-A2385-1G	1 g	$431.00 1/EA	Add To Favorites

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: A2385-100MG

Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	viruses
assay	≥98% (HPLC)
form	powder
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
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[C@H](CO)[C@@H](O)[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.
Biochem/physiol Actions:	Potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase.
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

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