CHEBI:2948 - azathioprine

ChEBI IDCHEBI:2948
ChEBI Nameazathioprine
Stars
DefinitionA thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS.
Last Modified13 June 2017
DownloadsMolfile
FormulaC9H7N7O2S
Net Charge0
Average Mass277.269
Monoisotopic Mass277.03819
SMILESCn1cnc([N+](=O)[O-])c1Sc1ncnc2ncnc12
InChIInChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChIKeyLMEKQMALGUDUQG-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
carcinogenic agent  A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
hepatotoxic agent  A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
Applications:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
azathioprine (CHEBI:2948) has role antimetabolite (CHEBI:35221)
azathioprine (CHEBI:2948) has role antineoplastic agent (CHEBI:35610)
azathioprine (CHEBI:2948) has role carcinogenic agent (CHEBI:50903)
azathioprine (CHEBI:2948) has role DNA synthesis inhibitor (CHEBI:59517)
azathioprine (CHEBI:2948) has role hepatotoxic agent (CHEBI:50908)
azathioprine (CHEBI:2948) has role immunosuppressive agent (CHEBI:35705)
azathioprine (CHEBI:2948) has role prodrug (CHEBI:50266)
azathioprine (CHEBI:2948) is a C-nitro compound (CHEBI:35716)
azathioprine (CHEBI:2948) is a aryl sulfide (CHEBI:35683)
azathioprine (CHEBI:2948) is a imidazoles (CHEBI:24780)
azathioprine (CHEBI:2948) is a thiopurine (CHEBI:35666)
IUPAC Name 
6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
Synonyms  Source
Imuran (TN)KEGG DRUG
6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purineChemIDplus
6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurineChemIDplus
Manual XrefsDatabases
C06837KEGG COMPOUND
D00238KEGG DRUG
AzathioprineWikipedia
DB00993DrugBank
269DrugCentral
Registry NumbersSources
Reaxys:1225351Reaxys
CAS:446-86-6KEGG DRUG
CAS:446-86-6ChemIDplus
Citations