CHEBI:2948 - azathioprine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name azathioprine
ChEBI ID CHEBI:2948
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C9H7N7O2S
Net Charge 0
Average Mass 277.26386
Monoisotopic Mass 277.038
InChI InChI=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)
InChIKey LMEKQMALGUDUQG-UHFFFAOYSA-N
SMILES Cn1cnc(c1Sc1ncnc2nc[nH]c12)[N+]([O-])=O
Roles Classification
Biological Role(s): 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.
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.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine ChemIDplus
6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine ChemIDplus
Imuran (TN) KEGG DRUG
Manual Xrefs Databases
269 DrugCentral
Azathioprine Wikipedia
C06837 KEGG COMPOUND
D00238 KEGG DRUG
DB00993 DrugBank
View more database links
Registry Numbers Types Sources
1225351 Reaxys Registry Number Reaxys
446-86-6 CAS Registry Number KEGG DRUG
446-86-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11064448 PubMed citation Europe PMC
15199672 PubMed citation Europe PMC
15476481 PubMed citation Europe PMC
15628319 PubMed citation Europe PMC
15973722 PubMed citation Europe PMC
16344342 PubMed citation Europe PMC
16397313 PubMed citation Europe PMC
16764353 PubMed citation Europe PMC
16954801 PubMed citation Europe PMC
17381669 PubMed citation Europe PMC
17970886 PubMed citation Europe PMC
18008354 PubMed citation Europe PMC
18336531 PubMed citation Europe PMC
19243907 PubMed citation Europe PMC
20080917 PubMed citation Europe PMC
25248004 PubMed citation Europe PMC
25314066 PubMed citation Europe PMC
25440430 PubMed citation Europe PMC
25443086 PubMed citation Europe PMC
25581826 PubMed citation Europe PMC
25641386 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
8738760 PubMed citation Europe PMC
9273463 PubMed citation Europe PMC
9345422 PubMed citation Europe PMC
Last Modified
13 June 2017