10302-78-0

Basic information

• Product Name: 2'',3'',5''-Triacetyl -azacytidine
• Synonyms: 2'',3'',5''-Triacetyl -azacytidine;1,3,5-Triazin-2(1H)-one, 4-amino-1-(2,3,5-tri-o-acetyl-.beta.-D-ribofuranosyl)-;Nsc291930;S-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-, triacetate (ester);2',3',5'-triacetyl-5-Azacytidine;1,3,5-Triazin-2(1H)-one, 4-aMino-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)-;(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(4-amino-2-oxo-1,3,5-triazin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate;Intermediate of Azacitidine
• CAS NO: 10302-78-0
• Molecular Formula: C14H18N4O8
• Molecular Weight: 370.316
• Mol File: 10302-78-0.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 497.3°Cat760mmHg
• Flash Point: 254.6°C
• Appearance: /
• Density: 1.6g/cm³
• Storage Temp.: Store at 0-5°C
• Solubility: ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
• PKA: 3.06±0.20(Predicted)
• CAS DataBase Reference: 2'',3'',5''-Triacetyl -azacytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'',3'',5''-Triacetyl -azacytidine(10302-78-0)
• EPA Substance Registry System: 2'',3'',5''-Triacetyl -azacytidine(10302-78-0)

Safety Data

• Hazardous Substances Data: 10302-78-0(Hazardous Substances Data)

Usage

Description

2'',3'',5''-Triacetyl -azacytidine is a prodrug form of 5-azacytidine, an inhibitor of DNA methyltransferase. It is designed to reverse epigenetic changes and reduce hypermethylation associated with certain diseases, such as myelodysplastic syndromes and cancer. 2'',3'',5''-Triacetyl -azacytidine can be rapidly absorbed orally without the formation of major metabolites in the gastrointestinal tract, making it a more bioavailable and convenient form of 5-azacytidine. It appears as a white to off-white powder.

Uses

Used in Pharmaceutical Industry:
2'',3'',5''-Triacetyl -azacytidine is used as an epigenetic modifier for the treatment of myelodysplastic syndromes and certain types of cancer. It works by inhibiting DNA methyltransferase, which helps to reverse the hypermethylation associated with these diseases and potentially restore normal gene function.
Used in Research Applications:
In the field of biological and medical research, 2'',3'',5''-Triacetyl -azacytidine is used as a research tool to study the effects of DNA methylation on gene expression and the development of diseases. It can also be employed to investigate the potential of epigenetic therapies in reversing or treating various conditions.
Used in Drug Development:
2'',3'',5''-Triacetyl -azacytidine serves as a starting point for the development of new drugs targeting epigenetic modifications. Its prodrug nature allows for improved oral bioavailability, which can be beneficial in the design of more effective and convenient therapeutic agents for the treatment of diseases related to DNA methylation.

in vivo

in cd-1 mice, oral administration of tac for five days per week for 2 weeks didn’t result in animal deaths and weight loss, but induced changes in hematological parameters, lymph nodes, bone marrow, and duodenal epithelium. tac inhibited global dna methylation in the spleen and gut. in an in vivo l1210 leukemia model, tac exhibited antineoplastic activity [1].

references

[1] ziemba a, ramirez m c, freeman b, et al. abstract# 3369: development of oral demethylating agents for the treatment of myelodysplastic syndrome[j]. 2009.[2] brueckner b, boy r g, siedlecki p, et al. epigenetic reactivation of tumor suppressor genes by a novel small-molecule inhibitor of human dna methyltransferases[j]. cancer research, 2005, 65(14): 6305-6311.

Downstream Products

• 320-67-2 5-azacytidine