CHEBI:9334 - sulfasalazine

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ChEBI Name sulfasalazine
ChEBI ID CHEBI:9334
Definition An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:101223
Supplier Information
Download Molfile XML SDF
Formula C18H14N4O5S
Net Charge 0
Average Mass 398.39300
Monoisotopic Mass 398.068
InChI InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+
InChIKey NCEXYHBECQHGNR-QZQOTICOSA-N
SMILES OC(=O)c1cc(ccc1O)\N=N\c1ccc(cc1)S(=O)(=O)Nc1ccccn1
Roles Classification
Biological Role(s): EC 2.5.1.18 (glutathione transferase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of a glutathione transferase (EC 2.5.1.18).
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sulfasalazine (CHEBI:9334) has functional parent sulfanilamide (CHEBI:45373)
sulfasalazine (CHEBI:9334) has role antiinfective agent (CHEBI:35441)
sulfasalazine (CHEBI:9334) has role EC 2.5.1.18 (glutathione transferase) inhibitor (CHEBI:76797)
sulfasalazine (CHEBI:9334) has role gastrointestinal drug (CHEBI:55324)
sulfasalazine (CHEBI:9334) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
sulfasalazine (CHEBI:9334) is a azobenzenes (CHEBI:22682)
sulfasalazine (CHEBI:9334) is a pyridines (CHEBI:26421)
sulfasalazine (CHEBI:9334) is a sulfonamide (CHEBI:35358)
IUPAC Name
2-hydroxy-5-{[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl}benzoic acid
INNs Sources
Salazosulfapiridina ChemIDplus
Salazosulfapyridinum ChemIDplus
Sulfasalazina ChemIDplus
sulfasalazine ChemIDplus
Sulfasalazinum ChemIDplus
Synonyms Sources
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid ChemIDplus
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acid ChEMBL
4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene ChemIDplus
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid ChemIDplus
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid ChemIDplus
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid ChemIDplus
Salazosulfapyridine KEGG COMPOUND
Salicylazosulfapyridine KEGG COMPOUND
Sulfasalazine KEGG COMPOUND
Brand Name Source
Azulfidine KEGG DRUG
Manual Xrefs Databases
C07316 KEGG COMPOUND
D00448 KEGG DRUG
DB00795 DrugBank
SAS PDBeChem
US2396145 Patent
View more database links
Registry Numbers Types Sources
2666050 Gmelin Registry Number Gmelin
356241 Beilstein Registry Number Beilstein
599-79-1 CAS Registry Number KEGG COMPOUND
599-79-1 CAS Registry Number ChemIDplus
8132868 Reaxys Registry Number Reaxys
8132868 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11362329 PubMed citation Europe PMC
11485124 PubMed citation Europe PMC
11587223 PubMed citation Europe PMC
14981898 PubMed citation Europe PMC
15248210 PubMed citation Europe PMC
16322111 PubMed citation Europe PMC
17386570 PubMed citation Europe PMC
2434548 PubMed citation Europe PMC
7720170 PubMed citation Europe PMC
Last Modified
08 February 2016