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Merck
CN

11385

5-Azacytidine

≥97.0% (HPLC)

Synonym(s):

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
EC Number:
206-280-2
UNSPSC Code:
12352203
MDL number:
MFCD00006539
Beilstein/REAXYS Number:
620461

Key Documents

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assay

≥97.0% (HPLC)

mp

226-232 °C (dec.) (lit.)

antibiotic activity spectrum

viruses

mode of action

DNA synthesis | interferes

storage temp.

2-8°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

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General description

Chemical structure: nucleoside

Application

Cancerostatic agent with weak antibiotic activity (gram-positive)

Biochem/physiol Actions

A potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase, an important regulatory mechanism of gene expression, gene activation and silencing.
Potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase.

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

WGK 3

ppe

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

Regulatory Information

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Alexandra Duverger et al.
Journal of virology, 83(7), 3078-3093 (2009-01-16)
Recent research has emphasized the notion that human immunodeficiency virus type 1 (HIV-1) latency is controlled by a restrictive histone code at, or DNA methylation of, the integrated viral promoter (long terminal repeat [LTR]). The present concept of HIV-1 latency
Ming-Xiang Zhang et al.
Molecular biology of the cell, 19(9), 3997-4005 (2008-07-11)
We have reported previously that the 27nt repeat polymorphism in endothelial nitric-oxide synthase (eNOS) intron 4--a source of 27nt small RNA--inhibits eNOS expression. In the current study, we have investigated how 27nt small RNA suppresses eNOS expression. Using a chromatin
Arkadiusz Gertych et al.
Cytometry. Part A : the journal of the International Society for Analytical Cytology, 75(7), 569-583 (2009-05-22)
Today's advanced microscopic imaging applies to the preclinical stages of drug discovery that employ high-throughput and high-content three-dimensional (3D) analysis of cells to more efficiently screen candidate compounds. Drug efficacy can be assessed by measuring response homogeneity to treatment within

Global Trade Item Number

SKUGTIN
307750-25G04061826673843
24-5390-5-500G-J04061832572185
105107500004022536061122
60235-1KG04061826714836
105107100004022536061108
307750-500G04061826673850

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