Azacitidine | CAS No. 320-67-2

Azacitidine

Basic Information

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CAS Number

320-67-2

Molecular Formula

C8H12N4O5

Molecular Weight

244.21 g/mol

Basic Physical Properties

Physical State

Powder

Melting Point

226-232 °C (dec.)

Boiling Point

534.5°C at 760 mmHg

Water Solubility

0.5-1.0 g/100 mL at 21 ºC

Flash Point

277 oC

Refractive Index

1.6590 (estimate)

Specific Rotation

40 º (C=1, H2O 22 ºC)

SMILES

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Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1

InChI

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

InChIKey

NMUSYJAQQFHJEW-KVTDHHQDSA-N

LogP

-3.1679999999999997

Topological Polar Surface Area

143.72000000000003 Å²

Hydrogen Bond Donor/Acceptor

5 / 9

Complexity

384

Safety Information

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GHS Hazard Pictograms

H302

H350

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H350 May cause cancer
Carcinogenicity

Toxicity

LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler)

Synonyms & References

English

5-Azacytidine
4-amino-1-beta-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
4-amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one
5-AC
5 AZC
5-AZCR
Antibiotic u 18496
Azacitidine
Azacytidine
ladakamycin
u 18496
wr 183027
4-amino-1-beta-d-ribofuranosyl-s-triazin-2(1h)-on
5-triazin-2(1h)-one,4-amino-1-beta-d-ribofuranosyl-3
mylosar
nci-c01569
nsc-102816
5-AZAC
4-AMINO-1-(BETA-D-RIBOFURANOSYL)-1,3,5-TRIAZIN-2(1H)-ONE
4-AMINO-1-[(2S,3S,4R,5S)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-1,3,5-TRIAZIN-2-ONE
5-Azacytidine (Vidaza®,Mylosar®, azacytidine, NSC 102816, NSC 103-627, Ladakamycin, U 18496,)
[14C]-Azacitidine
4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
5-AC-15N4
5-Azacitidine
5'-azacytidine
AzGR
Vidaza
4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one
5-AzaC
Ladakamycin

MDL Number

MFCD00006539

Customs Code

2934999090

FAQ

What is Azacitidine (CAS: 320-67-2)?

Azacitidine is a synthetic nucleoside analog with the chemical formula C9H12N4O4. It is known for its ability to inhibit DNA methylation and is used primarily in medical applications. As a cytosine analog, it has structural similarities to DNA bases and is often employed in cancer treatment, particularly for myelodysplastic syndromes. Its molecular structure and chemical properties make it a valuable compound in pharmaceutical research.

What are the main uses of Azacitidine (CAS: 320-67-2)?

Azacitidine is mainly used in the treatment of certain blood cancers, including myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML). It works by altering gene expression through DNA hypomethylation. Additionally, it is utilized in research for studying epigenetic mechanisms and has potential applications in other therapeutic areas. Its role as a DNA methyltransferase inhibitor makes it a key compound in oncology and molecular biology.

Is Azacitidine (CAS: 320-67-2) safe?

Azacitidine is generally considered safe when used as directed in medical settings. However, it can cause side effects such as nausea, vomiting, and myelosuppression. Proper handling and protective measures, like using gloves and ensuring good ventilation, are essential during its preparation and administration. Safety standards for Azacitidine are established by regulatory bodies to ensure its appropriate use in clinical and research contexts.

How should Azacitidine (CAS: 320-67-2) be stored?

Azacitidine should be stored in a cool, dry place away from light. It is typically kept in airtight containers at a temperature range of 2-8°C. Maintaining low humidity levels is crucial to prevent degradation. Proper storage ensures the stability and potency of the compound, which is important for both pharmaceutical and research applications.