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| {{drugbox
| | #REDIRECT [[Azacytidine]] |
| | IUPAC_name = 4-amino-1-[3,4-dihydroxy-5- (hydroxymethyl) oxolan-2-yl] -1,3,5-triazin-2-one
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| | image = Azacytidine.png
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| | CAS_number = 320-67-2
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| | ATC_prefix =
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| | ATC_suffix =
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| | ATC_supplemental =
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| | PubChem = 9444
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| | DrugBank = APRD00809
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| | C = 8 | H = 12 | N = 4 | O = 5
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| | molecular_weight = 244.205 g/mol
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| | bioavailability =
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| | metabolism =
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| }}
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| {{SI}}
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| ==Overview==
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| '''5-Azacytidine''' is a chemical [[analog (chemistry)|analogue]] of [[cytidine]], a [[nucleoside]] present in [[DNA]] and [[RNA]]. Cells in the presence of 5-azacytidine incorporate it into DNA during [[DNA replication|replication]] and RNA during [[Transcription (genetics)|transcription]]. The incorporation of 5-azacytidine 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. Inhibition of DNA occurs through the formation of stable complexes between the molecule and with DNA methyltransferases, thereby saturating the cells methylation machinery.
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| 5-azacytidine and its deoxy derivative [[decitabine]] (also known as 5-aza-2'deoxycytidine) were first synthesized in Czechoslovakia as potential chemotherapeutic agents for cancer.<ref>{{cite journal |author=Cihák A |title=Biological effects of 5-azacytidine in eukaryotes |journal=Oncology |volume=30 |issue=5 |pages=405–22 |year=1974 |pmid=4142650}}</ref>
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| It can be used ''in vitro'' to remove methyl groups from DNA. This may weaken the effects of gene silencing mechanisms that occurred prior to the methylation. Methylation events are therefore believed to secure the DNA in a silenced state. Demethylation may reduce the stability of silencing signals and thus confer relative gene activation.<ref>Whitelaw E and Garrick D (2005), ''The Epigenome, ''Chapter 7'','' ''In'': ''Mammalian Genomics'', Ed: Ruvinsky A & Marshall Graves JA, CABI Publishing, Wallingford, UK, ISBN 0851999107.</ref>
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| 5-azacytidine is mainly used in the treatment of [[myelodysplastic syndrome]]. It is marketed as Vidaza.<ref>[http://www.vidaza.com/ Vidaza web site].</ref>
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| ==References==
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| <references/>
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| ==External links==
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| *[http://www.virtualcancercentre.com/drugs.asp?drugid=3170 Vidaza / Azacitidine] Virtual Cancer Centre
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| *[http://www.epigeneticstation.com/cell-treatment-5-aza-2-deoxycytidine/ 5-Aza-2'-Deoxycytidine information and protocols to study DNA methylation]
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| {{DEFAULTSORT:Azacytidine, 5-}}
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| [[Category:Chemotherapeutic agents]]
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| [[Category:Nucleosides]]
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| [[Category:Orphan drugs]]
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| [[cs:Azacytidin]]
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| [[de:Azacitidin]]
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