SAS

2-HYDROXY-(5-([4-(2-PYRIDINYLAMINO)SULFONYL]PHENYL)AZO)BENZOIC ACID

Created:1999-07-08
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count42
Chiral Atom Count0
Bond Count44
Aromatic Bond Count18
2D diagram of SAS

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Chemical Component Summary

Name2-HYDROXY-(5-([4-(2-PYRIDINYLAMINO)SULFONYL]PHENYL)AZO)BENZOIC ACID
SynonymsSULFASALAZINE
Systematic Name (OpenEye OEToolkits)2-hydroxy-5-[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl-benzoic acid
FormulaC18 H14 N4 O5 S
Molecular Weight398.393
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=S(=O)(Nc1ncccc1)c3ccc(/N=N/c2cc(C(=O)O)c(O)cc2)cc3
SMILESCACTVS3.341OC(=O)c1cc(ccc1O)N=Nc2ccc(cc2)[S](=O)(=O)Nc3ccccn3
SMILESOpenEye OEToolkits1.5.0c1ccnc(c1)NS(=O)(=O)c2ccc(cc2)N=Nc3ccc(c(c3)C(=O)O)O
Canonical SMILESCACTVS3.341 OC(=O)c1cc(ccc1O)N=Nc2ccc(cc2)[S](=O)(=O)Nc3ccccn3
Canonical SMILESOpenEye OEToolkits1.5.0 c1ccnc(c1)NS(=O)(=O)c2ccc(cc2)/N=N/c3ccc(c(c3)C(=O)O)O
InChIInChI1.03 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+
InChIKeyInChI1.03 NCEXYHBECQHGNR-QZQOTICOSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00795 
NameSulfasalazine
Groups approved
DescriptionSulfasalazine is an anti-inflammatory drug structurally related to salicylates and other non-steroidal anti-inflammatory drugs. It is indicated for managing inflammatory diseases such as ulcerative colitis and rheumatoid arthritis (RA).[L39065, A255582] Metabolized by intestinal bacteria, sulfasalazine is broken down into [mesalazine] and [sulfapyridine], 2 compounds that carry out the main pharmacological activity of sulfasalazine.[A255582] Sulfasalazine was first used in 1940 for rheumatic polyarthritis, and has been firmly established itself as one fo the most useful disease-modifying antirheumatic drug (DMARD).[A255582] Compared to the first line treatment of RA like methotrexate, sulfasalazine is almost as efficacious as methotrexate although with slightly less tolerability. However, sulfasalazine has less teratogenic side effects and faster onset of action compared to conventional DMARD.[A255582] Sulfasalazine fell out of favor as the drug of choice for RA due to poorly designed clinical trials in 1950 but regained interest from the clinical community in the late 1970.[A255582] Although sulfasalazine is only approved by the FDA for ulcerative colitis, research have shown that sulfasalazine is also beneficial for patients with Crohn's disease.[A255592] Meta-analysis of 19 randomized controlled trials indicated that sulfasalazine is superior to placebo in inducing remission; however, with no supported evidence of mucosal healing, sulfasalazine is not FDA-recommmended for treatment of Crohn's disease.[A255597,A255602,A255607]
Synonyms
  • 5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid
  • Salicylazosulfapyridine
  • 5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid
  • Azopyrin
  • 2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acid
Brand Names
  • Azulfidine
  • Salazopyrin En-tabs 500 mg
  • PMS-sulfasalazine-E.C. Tab 500mg
  • Sas Enema 3gm/100ml
  • PMS-sulfasalazine 500mg/tab USP
IndicationIn the US, sulfasalazine is indicated to treat mild to moderate ulcerative colitis and to prolong the remission period between acute attacks of ulcerative colitis.[L39065] Sulfasalazine is also indicated as an adjunct therapy in severe ulcerative colitis.[L39065]For the delayed-release tablet formulation, sulfasalazine is also indicated to treat rheumatoid arthritis in pediatric patients who have responded inadequately to salicylates or other nonsteroidal anti-inflammatory drugs or polyarticular-course juvenile rheumatoid arthritis with the same patients' characteristics.[L39065]
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Alimentary Tract and Metabolism
  • Amides
  • Aminosalicylate
ATC-Code
  • G01AE10
  • A07EC01
CAS number599-79-1

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Broad substrate specificity ATP-binding cassette transporter ABCG2MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...unknowninhibitor
Transcription factor RelBMLRSGPASGPSVPTGRAMPSRRVARPPAAPELGALGSPDLSSLSLAVSRS...unknownactivator
Transcription factor p65MDELFPLIFPAEPAQASGPYVEIIEQPKQRGMRFRYKCEGRSAGSIPGER...unknownactivator
Proto-oncogene c-RelMASGAYNPYIEIIEQPRQRGMRFRYKCEGRSAGSIPGEHSTDNNRTYPSI...unknownactivator
Polyunsaturated fatty acid 5-lipoxygenaseMPSYTVTVATGSQWFAGTDDYIYLSLVGSAGCSEKHLLDKPFYNDFERGA...unknowninhibitor
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

Related Resource References

Resource NameReference
CCDC/CSD QIJZOY, QIJZOY03
COD 2011879