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A2385

5-Azacytidine

Name: 5-Azacytidine
Brand: SIGMA

≥98% (HPLC), powder, DNA methyltransferase inhibitor

Synonym(s):

5-Azacitidine, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin

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About This Item

Empirical Formula (Hill Notation):

C₈H₁₂N₄O₅

CAS Number:

320-67-2

Molecular Weight:

244.20

NACRES:

NA.77

PubChem Substance ID:

24278211

UNSPSC Code:

12352200

EC Number:

206-280-2

MDL number:

MFCD00006539

Beilstein/REAXYS Number:

620461

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

5-Azacytidine, ≥98% (HPLC)

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

Chemical structure: nucleoside

5-Azacytidine is a chemical analog of cytidine. It functions as a hypomethylating agent. 5-Azacytidine is used to treat myelodysplastic syndrome (MDS).

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

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.

Potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase.

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 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.

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pictograms

GHS08,GHS07,GHS09

signalword

Danger

hcodes

H302,H341,H350,H360FD,H372,H410

pcodes

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

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

wgk

WGK 3

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

A2385-100MG:4.548173379203E12 + A2385-1G:4.54817337921E12 + A2385-250MG:4.548173379227E12

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Articles

Carcinogenesis and Epigenetics

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