MilliporeSigma
  • A2385
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
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

1 of 4

This Item
A1287PHR19111045520
5-Azacytidine ≥98% (HPLC)

Sigma-Aldrich

A2385

5-Azacytidine

5-Azacytidine Hybri-Max™, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma

Sigma-Aldrich

A1287

5-Azacytidine

Azacitidine Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1911

Azacitidine

Azacitidine United States Pharmacopeia (USP) Reference Standard

USP

1045520

Azacitidine

assay

≥98% (HPLC)

assay

-

assay

-

assay

-

form

powder

form

lyophilized powder

form

powder

form

-

originator

Celgene

originator

-

originator

-

originator

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

-

mp

226-232 °C (dec.) (lit.)

mp

226-232 °C (dec.) (lit.)

mp

226-232 °C (dec.) (lit.)

mp

226-232 °C (dec.) (lit.)

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

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.
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.

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.
This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Signal Word

Danger

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service