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A2385

Sigma-Aldrich

5-Azacytidine

≥98% (HPLC)

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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/REAXYS Number:
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

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1 of 4

This Item
PHR1911A1287A3656
5-Azacytidine ≥98% (HPLC)

A2385

5-Azacytidine

Azacitidine Pharmaceutical Secondary Standard; Certified Reference Material

PHR1911

Azacitidine

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

A1287

5-Azacytidine

5-Aza-2′-deoxycytidine ≥97%

A3656

5-Aza-2′-deoxycytidine

assay

≥98% (HPLC)

assay

-

assay

-

assay

≥97%

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

originator

Celgene

originator

-

originator

-

originator

Eisai

mp

226-232 °C (dec.) (lit.)

mp

226-232 °C (dec.) (lit.)

mp

226-232 °C (dec.) (lit.)

mp

-

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.

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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SAHA ≥98% (HPLC)

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Zebularine A cell-permeable chemically stable cytidine analog that displays antitumor properties.

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Azacitidine Related Compound B United States Pharmacopeia (USP) Reference Standard

USP

1045541

Azacitidine Related Compound B

Dexamethasone regulates EphA5, a potential inhibitory factor with osteogenic capability of human bone marrow stromal cells
Yamada T, et al.
Stem Cells International, 2016 (2016)
5-Azacytidine selectively increases gamma-globin synthesis in a patient with beta thalassemia
Ley TJ and DeSimone, et al.
The New England Journal of Medicine, 307(24), 1469-1475 (1982)
Circular RNA expression profiles during the differentiation of human umbilical cord-derived mesenchymal stem cells into cardiomyocyte-like cells
Ruan ZB, et al.
Journal of Cellular Physiology (2019)
Myogenic differentiation potential of mesenchymal stem cells derived from fetal bovine bone marrow
Okamura LH, et al.
Animal Biotechnology, 29(1), 1-11 (2018)
5-Azacytidine in the Treatment of Intermediate-2 and High-risk Myelodysplastic Syndromes and Acute Myeloid Leukemia. A Five-year Experience with 44 Consecutive Patients.
Diamantopoulos P, et al.
Anticancer Research, 35(9), 5141-5147 (2015)

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