[320-67-2] 5-Azacytidine AKSci E730
 
 
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  Catalog ID # E730
5-Azacytidine
, 98% (HPLC)
 
4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
5-Azacitidine
Ladakamycin




IDENTITY
CAS Number:[320-67-2]
MDL Number:MFCD00006539
MF:C8H12N4O5
MW:244.2047
EINECS:206-280-2
BRN:620461
SPECIFICATIONS & PROPERTIES
Purity:98% (HPLC)
Available Spectra:NMR, LCMS, FT-IR, HPLC, Polarimetry
Physical Form:White to off-white powder
Melting Point:207-224°C
Optical Rotation:+36° - +42° (c=1, H2O)
Long-Term Storage:Store long-term at -20°C

BIOLOGICAL INFO
Application(s):Inhibits DNA methyltransferase

REVIEW

 Azacitidine (5-azacytidine) is a chemical analogue of the cytosine nucleoside used in DNA and RNA. Azacitidine is thought to induce antineoplastic activity via two mechanisms; inhibition of DNA methyltransferase at low doses, causing hypomethylation of DNA, and direct cytotoxicity in abnormal hematopoietic cells in the bone marrow through its incorporation into DNA and RNA at high doses, resulting in cell death. As azacitidine is a ribonucleoside, it incoporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissembly of polyribosomes, defective methylation and acceptor function of transfer RNA, and inhibition of the production of protein. Its incorporation into DNA leads to a covalent binding with DNA methyltransferases, which prevents DNA synthesis and subsequent cytotoxicity.

REFERENCES
[1]Cihak A: Biological effects of 5-azacytidine in eukaryotes. Oncology. 1974;30(5):405-22.
[2] Kaminskas E, Farrell AT, Wang YC, Sridhara R, Pazdur R: FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist. 2005 Mar;10(3):176-82.
[3] Leone G, Voso MT, Teofili L, Lubbert M: Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS. Clin Immunol. 2003 Oct;109(1):89-102.
[4] Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422.

GHS

Pictograms

Signal Word
Danger

Hazard Statements
H302; H350

Precautionary Statements
P201; P202; P264; P270; P281; P301+P312; P308+P313; P330; P405; P501


Current as of December 4, 2016


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CATEGORIES

 APIs and Bioactives > Chemotherapeutics
 Nucleobases > Nucleosides

USEFUL LINKS

  PubChem