JBC

5-[(E)-(3-carboxy-4-oxidanyl-phenyl)diazenyl]-2-oxidanyl-benzoic acid

Created: 2021-05-12
Last modified:  2022-01-19

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Chemical Details

Formal Charge0
Atom Count32
Chiral Atom Count0
Bond Count33
Aromatic Bond Count12
2D diagram of JBC

Chemical Component Summary

Name5-[(E)-(3-carboxy-4-oxidanyl-phenyl)diazenyl]-2-oxidanyl-benzoic acid
Systematic Name (OpenEye OEToolkits)5-[(~{E})-(3-carboxy-4-oxidanyl-phenyl)diazenyl]-2-oxidanyl-benzoic acid
FormulaC14 H10 N2 O6
Molecular Weight302.239
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385OC(=O)c1cc(ccc1O)N=Nc2ccc(O)c(c2)C(O)=O
SMILESOpenEye OEToolkits2.0.7c1cc(c(cc1N=Nc2ccc(c(c2)C(=O)O)O)C(=O)O)O
Canonical SMILESCACTVS3.385 OC(=O)c1cc(ccc1O)N=Nc2ccc(O)c(c2)C(O)=O
Canonical SMILESOpenEye OEToolkits2.0.7 c1cc(c(cc1/N=N/c2ccc(c(c2)C(=O)O)O)C(=O)O)O
InChIInChI1.03 InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+
InChIKeyInChI1.03 QQBDLJCYGRGAKP-FOCLMDBBSA-N

Drug Info: DrugBank

DrugBank IDDB01250 
NameOlsalazine
Groups approved
DescriptionOlsalazine is an aminosalicylate and a prodrug of [mesalamine] (5-aminosalicylic acid, 5-ASA).[A257063] It was first developed for delivering mesalamine to the colon without the use of [sulfapyridine].[A257078] Olsalazine comprises two mesalamine molecules joined by an azo bridge, which is cleaved in the colon.[A257078] Olsalazine is an anti-inflammatory agent that works by inhibiting cyclooxygenase and lipoxygenase, subsequently reducing the production of pro-inflammatory factors like prostaglandin and leukotriene.[A257063] Olsalazine is used in the treatment of ulcerative colitis.[L45023,L45151]
Synonyms
  • Olsalazine
  • Olsalazine sodium
Brand NamesDipentum
IndicationIn the US, olsalazine is indicated for the maintenance of remission of ulcerative colitis in adult patients who are intolerant to [sulfasalazine].[L45023] In Canada, it is used in the treatment of acute ulcerative colitis of mild to moderate severity, with or without the concomitant use of steroids. It is also indicated for the long-term maintenance of patients with ulcerative colitis in remission.[L45151]
Categories
  • Acids, Carbocyclic
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Alimentary Tract and Metabolism
  • Aminosalicylate
ATC-CodeA07EC03
CAS number15722-48-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Human CyclooxygenasesMSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
Thiopurine S-methyltransferaseMDGTRTSLDIEEYSDTEVQKNQVLTLEEWQDKWVNGKTAFHQEQGHQLLK...unknowninhibitor
Interferon gammaMKYTSYILAFQLCIVLGSLGCYCQDPYVKEAENLKKYFNAGHSDVADNGT...unknown
Xanthine dehydrogenase/oxidaseMTADKLVFFVNGRKVVEKNADPETTLLAYLRRKLGLSGTKLGCGEGGCGA...unknowninhibitor
Solute carrier family 2, facilitated glucose transporter member 9MARKQNRNSKELGLVPLTDDTSHAGPPGPGRALLECDHLRSGVPGGRRRK...unknowndownregulator
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682