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320-67-2 (5-Azacytidine)

1

Identification

5-Azacytidine 5-Azacytidine
Name 5-Azacytidine
Formula C8H12N4O5
MW 244.2
CAS No. 320-67-2
EINECS 206-280-2
Smiles OC[[email protected]@H]1[[email protected]]([[email protected]]([[email protected]](N2C(N=C(N=C2)N)=O)O1)O)O
Synonyms 4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one; 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one
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
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Introduction

5-Azacitidine(5-AzaC) is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. IC50 Value: Azacitidine inhibits the L1210 cells growth with IC50 and of 0.019 μg/mL. Target: DNMT in vitro: Azacitidine is widely used to demonstrate the correlation between loss of methylation in specifc gene regions and activation of the associated genes.

Background Information

Azacitidine (Vidaza) is used in the treatment of myelodysplastic syndrome. Cells in the presence of azacitidine incorporate it into DNA during replication and into RNA during transcription. The incorporation of azacitidine into DNA or RNA inhibits methyltransferase thereby causing demethylation in that sequence, affecting the way that cell regulation proteins are able to bind to the DNA/RNA substrate. ......by AbMole BioScience
Azacitidine is a chemical analogue of the cytosine nucleoside used in DNA and RNA that is mainly used in the treatment of myelodysplastic syndrome (MDS). ......by AdooQ BioScience, LLC
Description ......by Apexbio Technology LLC
Azacitidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. ......by BOC Sciences
A potent growth inhibitor and cytotoxic agent; a potent DNA methyltransferase inhibitor. Causes DNA demethylation or hemi-demethylation, creating openings that allow transcription factors to bind to DNA and reactivate tumor suppressor genes. Also recently shown to increase reprogramming efficiency of stem cells 10-fold. ......by BioVision, Inc.,
5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. ......by MedChemexpress Co., Ltd.
Azacitidine is a pyrimidine nucleoside analogue of cytidine with antineoplastic activity. Azacitidine is incorporated into DNA, where it reversibly inhibits DNA methyltransferase, thereby blocking DNA methylation. Hypomethylation of DNA by azacitidine may activate tumor suppressor genes silenced by hypermethylation, resulting in an antitumor effect. This agent is also incorporated into RNA, thereby disrupting normal RNA function and impairing tRNA cytosine-5-methyltransferase activity. ......by MedKoo Biosciences, Inc.
A chemical analog of Cytidine that inhibits DNA methyltransferase; induces mitochondrial apoptosis and autophagy.Chemotherapeutic AgentsApproved ......by ProbeChem
Azacitidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. ......by Selleck Chemicals LLC
A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent. ......by Target Molecule Corp.
DNA methyltransferase inhibitor. Incorporates into DNA forming covalent adducts with cellular DNMT1, depleting enzyme activity. Induces demethylation and reactivation of silenced genes. Improves the efficiency of reprogramming of stem cells; induces differentiation of mesenchymal stem cells into cardiomyocytes. ......by Tocris Bioscience Inc.
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Protocol(Only for Reference)

Cell Experiment

Cell lines Leukemia L1210 cell
Conditions 0.15 μg/mL; 3 days
Method 5 mL of L1210 cells (5 × 103 cells/mL) are incubated with Azacitidine at 37 ℃ for 3 days. Cell number is determined twice a day for 3 days by means of a Model A Coulter counter.
Source Selleck Chemicals LLC

Animal Experiment

Animal Models BDF1 mice bearing lymphoid leukemia L1210
Dosage 3 mg/kg
Formulation Dissolved in 0.85% NaC1 solution immediately prior to use
Administration Daily i.p. injection
Source Selleck Chemicals LLC
4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000024210

Storage condition

Storage condition:Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). Stock solution storage:0 - 4 C for short term (days to weeks), or -20 C for long term (months). Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. by MedKoo Biosciences, Inc.

Solubility

DMSO 49 mg/mL; Water <1 mg/mL; Ethanol <1 mg/mL by MedChemexpress Co., Ltd.
Soluble in DMSO, not in water by MedKoo Biosciences, Inc.
(25°C) * In vitro DMSO 48 mg/mL warming (196.56 mM); Water<1 mg/mL (<1 mM); Ethanol<1 mg/mL (<1 mM); In vivo 30% Propylene glycol, 5% Tween 80, 65% D5W30 mg/mL by Selleck Chemicals LLC
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Mechanism and Indication

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
5-Azacytidine Eisai Inc Myelodysplastic syndrome 2009/11/30 2011/1/1 Phase 4 Clinical
5-Azacytidine MD Anderson Cancer Center Leukemia 2013/3/31 2015/3/31 Phase 3 Clinical
5-Azacytidine Seoul National University Hospital Myelodysplastic syndrome 2011/1/31 2011/12/1 Phase 3 Clinical
5-Azacytidine Celgene Corp Myelodysplastic syndrome 2007/4/30 2009/9/30 Phase 3 Clinical
5-Azacytidine Celgene Corp Acute myelogenous leukemia 2010/6/30 2013/10/31 Phase 3 Clinical
5-Azacytidine - Launched
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Safety Data of 5-Azacytidine

Hazard Symbols : T
Risk Statements : R45;R46;R22
Safety Statements : S53;S22;S36/37/39;S45
RTECS : XZ3017500
WGKGermany : 3
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Spectral Information

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Suppliers List

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Related Products

Other Forms of 320-67-2

Name CAS No Formula MW

Recommended Compounds in Nucleoside Antimetabolite/Analog Autophagy

Name CAS No Formula MW
5-BrdU 59-14-3 C9H11BrN2O5 307.1
Vidarabine 5536-17-4 C10H13N5O4 267.24
Adenosine 58-61-7 C10H13N5O4 267.24
Carmofur 61422-45-5 C11H16FN3O3 257.26
Cytidine 65-46-3 C9H13N3O5 243.22
Merimepodib 198821-22-6 C23H24N4O6 452.46
Floxuridine 50-91-9 C9H11FN2O5 246.19
Dacarbazine 4342-03-4 C6H10N6O 182.18
Tipiracil (hydrochloride) 183204-72-0 C9H12Cl2N4O2 279.12
Trifluorothymidine 70-00-8 C10H11F3N2O5 296.2
Orotic acid 65-86-1 C5H4N2O4 156.1
Nelarabine 121032-29-9 C11H15N5O5 297.27
6-Mercaptopurine 50-44-2 C5H4N4S 152.18
LY2334737 892128-60-8 C17H25F2N3O5 389.39
Cytarabine (hydrochloride) 69-74-9 C9H14ClN3O5 279.68
Cytarabine 147-94-4 C9H13N3O5 243.22
Gemcitabine (elaidate) 210829-30-4 C27H43F2N3O5 527.6442
Tegafur 17902-23-7 C8H9FN2O3 200.17
Fludarabine 21679-14-1 C10H12FN5O4 285.23
Triciribine 35943-35-2 C13H16N6O4 320.3

Recommended Compounds in Same Indication

Name CAS No Formula MW
AZD1152 722543-31-9 C26H31FN7O6P 587.54
AZD1152-HQPA 722544-51-6 C26H30FN7O3 507.56
Mocetinostat 726169-73-9 C23H20N6O 396.44
Volasertib 755038-65-4 C34H50N8O3 618.81
KX2-391 897016-82-9 C26H29N3O3 431.53
MLN4924 905579-51-3 C21H25N5O4S 443.52
IDO5L 914471-09-3 C9H7ClFN5O2 271.6356
Panobinostat 404950-80-7 C21H23N3O2 349.43
Rigosertib 592542-59-1 C21H25NO8S 451.49
ON-019190 (sodium) 1225497-78-8 C21H24NNaO8S 473.4719
Crenolanib 670220-88-9 C26H29N5O2 443.54
ARRY-520 (R enantiomer) 885060-08-2 C20H22F2N4O2S 420.48
ARRY-520 885060-09-3 C20H22F2N4O2S 420.48
LY2090314 603288-22-8 C28H25FN6O3 512.53
Ezatiostat 168682-53-9 C27H35N3O6S 529.65
Posaconazole 171228-49-2 C37H42F2N8O4 700.78
Decitabine 2353-33-5 C8H12N4O4 228.21
2-(2-chlorophenyl)-5,7-dihydroxy-8-((3R,4S)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-one C21H20ClNO5 401.8402
Lenalidomide 191732-72-6 C13H13N3O3 259.26
Tipifarnib 192185-72-1 C27H22Cl2N4O 489.4
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Route of Synthesis

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References

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More Information

5-Azacytidine

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