Sulfasalazine (CHEM002273)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:39 UTC
Update Date2016-11-09 01:08:43 UTC
Accession NumberCHEM002273
Identification
Common NameSulfasalazine
ClassSmall Molecule
DescriptionSulfasalazine is only found in individuals that have used or taken this drug. It is a drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see mesalamine) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907)The mode of action of Sulfasalazine or its metabolites, 5-aminosalicylic acid (5-ASA) and sulfapyridine (SP), is still under investigation, but may be related to the anti-inflammatory and/or immunomodulatory properties that have been observed in animal and in vitro models, to its affinity for connective tissue, and/or to the relatively high concentration it reaches in serous fluids, the liver and intestinal walls, as demonstrated in autoradiographic studies in animals. In ulcerative colitis, clinical studies utilizing rectal administration of Sulfasalazine, SP and 5-ASA have indicated that the major therapeutic action may reside in the 5-ASA moiety. The relative contribution of the parent drug and the major metabolites in rheumatoid arthritis is unknown.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Anti-Infective Agent
  • Anti-Inflammatory Agent, Non-Steroidal
  • Antirheumatic Agent
  • Drug
  • Gastrointestinal Agent
  • Metabolite
  • Organic Compound
  • Sulfonamide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acidChEBI
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acidChEBI
4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzeneChEBI
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acidChEBI
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acidChEBI
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acidChEBI
AzulfidineChEBI
SalazosulfapiridinaChEBI
SalazosulfapyridineChEBI
SalazosulfapyridinumChEBI
SalicylazosulfapyridineChEBI
SulfasalazinaChEBI
SulfasalazinumChEBI
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoateGenerator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoateGenerator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoic acidGenerator
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoateGenerator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoateGenerator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoic acidGenerator
4-(Pyridyl-2-amidosulphonyl)-3'-carboxy-4'-hydroxyazobenzeneGenerator
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylateGenerator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylateGenerator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylic acidGenerator
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoateGenerator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoateGenerator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoic acidGenerator
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylateGenerator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylateGenerator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylic acidGenerator
SalazosulphapiridinaGenerator
SalazosulphapyridineGenerator
SalazosulphapyridinumGenerator
SalicylazosulphapyridineGenerator
SulphasalazinaGenerator
SulphasalazinumGenerator
SulphasalazineGenerator
SulfasalazinHMDB
Chemical FormulaC18H14N4O5S
Average Molecular Mass398.393 g/mol
Monoisotopic Mass398.068 g/mol
CAS Registry Number599-79-1
IUPAC Name2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid
Traditional Namesulfasalazine
SMILESOC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1
InChI IdentifierInChI=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+
InChI KeyNCEXYHBECQHGNR-QZQOTICOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzobenzenes
Sub ClassNot Available
Direct ParentAzobenzenes
Alternative Parents
Substituents
  • Azobenzene
  • Benzenesulfonamide
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • Salicylic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzenesulfonyl group
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Organosulfonic acid amide
  • Heteroaromatic compound
  • Vinylogous acid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Azo compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point220 dec°C
Boiling PointNot Available
Solubility4.64e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.92ALOGPS
logP3.94ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)2.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area141.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.6 m³·mol⁻¹ChemAxon
Polarizability39.69 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6w-6695000000-47b5c3a0d5190268e477Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-2549110000-cce76e754cd947c9bdf8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0239100000-5bf223e6e250eb77105aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-9e5b613387b866753d70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-2019000000-5dbdcf5699c56f6a59d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9240000000-6268787fab73d296c1d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0009000000-5eea07137968cfa96d18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-642c65b2544ce824deccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k97-9663000000-5acc71d633a9ef82ea98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-a266ecec49bba90668baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005a-2089000000-ad13a0c69c0256eb5505Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0092-3936000000-d0a391d2c705ca56748eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-cf36a51de9de200e8014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2917000000-1f1274dcd32e5287cfb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1900000000-16464eaa00e58b69be2dSpectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityThe mode of action of Sulfasalazine or its metabolites, 5-aminosalicylic acid (5-ASA) and sulfapyridine (SP), is still under investigation, but may be related to the anti-inflammatory and/or immunomodulatory properties that have been observed in animal and in vitro models, to its affinity for connective tissue, and/or to the relatively high concentration it reaches in serous fluids, the liver and intestinal walls, as demonstrated in autoradiographic studies in animals. In ulcerative colitis, clinical studies utilizing rectal administration of Sulfasalazine, SP and 5-ASA have indicated that the major therapeutic action may reside in the 5-ASA moiety. The relative contribution of the parent drug and the major metabolites in rheumatoid arthritis is unknown.
Metabolism Route of Elimination: The majority of 5-ASA stays within the colonic lumen and is excreted as 5-ASA and acetyl-5-ASA with the feces. Half Life: 5-10 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Uses/SourcesUsed primarily as an anti-inflammatory agent in the treatment of inflammatory bowel disease as well as for rheumatoid arthritis.
Minimum Risk LevelNot Available
Health EffectsSulfasalazine in rare cases can cause severe depression in young males. Immune thrombocytopenia has been reported. [Wikipedia]
SymptomsNot Available
TreatmentGastric lavage or emesis plus catharsis as indicated. Alkalinize urine. If kidney function is normal, force fluids. If anuria is present, restrict fluids and salt, and treat appropriately. Catheterization of the ureters may be indicated for complete renal blockage by crystals. The low molecular weight of sulfasalazine and its metabolites may facilitate their removal by dialysis. (2)
Concentrations
Not Available
DrugBank IDDB00795
HMDB IDHMDB0014933
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSulfasalazine
Chemspider ID10605946
ChEBI ID9334
PubChem Compound IDNot Available
Kegg Compound IDC07316
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11362329
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11485124
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11587223
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14981898
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15248210
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16322111
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17386570
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=2434548
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7720170