Merck
All Photos(4)

A2385

Sigma-Aldrich

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:
Molecular Weight:
244.20
Beilstein:
620461
Número de EC:
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

200

ensayo

≥98% (HPLC)

formulario

powder

mp

226-232 °C (dec.) (lit.)

espectro de actividad antibiótica

viruses

Modo de acción

DNA synthesis | interferes

emisor

Celgene

temp. de almacenamiento

−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

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Descripción general

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

Aplicación

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

Envase

100, 250 mg in poly bottle
1 g in poly bottle

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Palabra de señalización

Danger

Clasificaciones de peligro

Acute Tox. 4 Oral - Aquatic Chronic 1 - Carc. 1A - Muta. 2 - Repr. 1B - STOT RE 1

Código de clase de almacenamiento

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Equipo de protección personal

Eyeshields, Gloves, type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Certificate of Analysis

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Certificate of Origin

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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.

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