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Azaserine: Difference between revisions

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Revision as of 00:13, 1 September 2011 editBogBot (talk | contribs)Bots53,132 edits populated new fields in {{drugbox}} and reordered per bot approval. Report errors and suggestions to User_talk:BogBot← Previous edit Revision as of 21:44, 17 October 2011 edit undoThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKeyNext edit →
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| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1095699 | ChEMBL = 1095699
| ChemSpiderID = 16735688
| SMILES = O=C(OC(N)C(O)=O)/C==
| InChI = 1/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1
| InChIKey = MZZGOOYMKKIOOX-VKHMYHEABI
| StdInChI = 1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1
| StdInChIKey = MZZGOOYMKKIOOX-VKHMYHEASA-N


<!--Chemical data--> <!--Chemical data-->

Revision as of 21:44, 17 October 2011

Pharmaceutical compound
Azaserine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • O-(2-Diazoacetyl)-L-serine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.003.692 Edit this at Wikidata
Chemical and physical data
FormulaC5H7N3O4
Molar mass173.127 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C(OC(N)C(O)=O)/C==
InChI
  • InChI=1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1
  • Key:MZZGOOYMKKIOOX-VKHMYHEASA-N
  (what is this?)  (verify)

Azaserine is a carcinogen primarily used for researching pancreatic cancer in animal models. It is a glutamine analogue that irreversibly inhibits glutamine utilizing enzymes such as Gln: Phosphoribosyl Amidotransferase, which is involved in the biosynthesis of Inosine monophosphate (IMP). IMP is an important precursor to the purine nucleotides which include Adenosine monophosphate (AMP) and Guanosine monophosphate (GMP).

Further enzymes of purine and pyrimidine metabolism are inhibited as well. Therefore it was tested as anti-cancer drug by different authors in different indications (not only pancreatic cancer) in pre-clinical settings. Further glutamine analogues that were tested as anti-cancer drugs are DON and Acivicin.


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