ContaminantDB: Sulfasalazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (49)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:39 UTC

Update Date

2026-05-14 16:49:11 UTC

Accession Number

CHEM002273

Identification

Common Name

Sulfasalazine

Class

Small Molecule

Description

Sulfasalazine belongs to the azobenzenes, a class of organoheterocyclic compounds within the organic compounds. This exogenous compound has the formula C18H14N4O5S and an average molecular weight of 398.39 g/mol. At room temperature, it exists as a solid. It is used as a gastrointestinal drug, a non-steroidal anti-inflammatory drug, and an antiinfective agent. It is found in drinking water and water supply, as well as in healthcare, pharmaceuticals, and veterinary products, including antibiotics, gynecologicals, and intestinal antiinflammatory agents. Recorded exposure routes include oral, rectal, and inhalation. The compound interacts with 24 recorded protein targets. It acts as an activator or inhibitor of the inhibitor of nuclear factor kappa-B kinase subunit alpha (CHUK), inhibitor of nuclear factor kappa-B kinase subunit beta (IKBKB), prostaglandin G/H synthase 2 (PTGS2), and peroxisome proliferator-activated receptor gamma (PPARG). Additionally, it targets the mitochondrial acetyl-CoA acetyltransferase (ACAT1) and the cystine/glutamate transporter (SLC7A11), among 18 other proteins. The mode of action of sulfasalazine or its metabolites, sulfapyridine (SP) and 5-aminosalicylic acid (5-ASA), is still under investigation. This action may be related to its affinity for connective tissue, the relatively high concentration it reaches in the liver, serous fluids, and intestinal walls as demonstrated in animal autoradiographic studies, and the anti-inflammatory or immunomodulatory properties observed in in vitro and animal models. In cases of ulcerative colitis, clinical studies using rectal administration of 5-ASA, SP, and sulfasalazine indicate that the major therapeutic action may reside in the 5-ASA moiety. The relative contribution of the major metabolites and the parent drug 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
Human Neurotoxin
Metabolite
Organic Compound
Sulfonamide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid	ChEBI
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acid	ChEBI
4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene	ChEBI
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid	ChEBI
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid	ChEBI
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid	ChEBI
Azulfidine	ChEBI
Salazosulfapiridina	ChEBI
Salazosulfapyridine	ChEBI
Salazosulfapyridinum	ChEBI
Salicylazosulfapyridine	ChEBI
Sulfasalazina	ChEBI
Sulfasalazinum	ChEBI
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoate	Generator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoate	Generator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoic acid	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoate	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoate	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoic acid	Generator
4-(Pyridyl-2-amidosulphonyl)-3'-carboxy-4'-hydroxyazobenzene	Generator
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylate	Generator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylate	Generator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylic acid	Generator
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoate	Generator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoate	Generator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoic acid	Generator
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylate	Generator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylate	Generator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylic acid	Generator
Salazosulphapiridina	Generator
Salazosulphapyridine	Generator
Salazosulphapyridinum	Generator
Salicylazosulphapyridine	Generator
Sulphasalazina	Generator
Sulphasalazinum	Generator
Sulphasalazine	Generator
Sulfasalazin	HMDB

Chemical Formula

C₁₈H₁₄N₄O₅S

Average Molecular Mass

398.393 g/mol

Monoisotopic Mass

398.068 g/mol

CAS Registry Number

599-79-1

IUPAC Name

2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid

Traditional Name

sulfasalazine

SMILES

OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1

InChI Identifier

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+

InChI Key

NCEXYHBECQHGNR-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azobenzenes

Sub Class

Not Available

Direct Parent

Azobenzenes

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:9334 )
azobenzenes (CHEBI:9334 )
pyridines (CHEBI:9334 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Sulfasalazine Action Pathway	SMP0126115	Not Available
Sulfasalazine Drug Metabolism Action Pathway	SMP0143234	Not Available

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	220 dec°C
Boiling Point	Not Available
Solubility	4.64e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.94	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	2.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	141.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.6 m³·mol⁻¹	ChemAxon
Polarizability	39.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6w-6695000000-47b5c3a0d5190268e477	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-2549110000-cce76e754cd947c9bdf8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0239100000-5bf223e6e250eb77105a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-9e5b613387b866753d70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-2019000000-5dbdcf5699c56f6a59d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9240000000-6268787fab73d296c1d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0009000000-5eea07137968cfa96d18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-642c65b2544ce824decc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k97-9663000000-5acc71d633a9ef82ea98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-a266ecec49bba90668ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-005a-2089000000-ad13a0c69c0256eb5505	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0092-3936000000-d0a391d2c705ca56748e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-cf36a51de9de200e8014	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2917000000-1f1274dcd32e5287cfb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-1900000000-16464eaa00e58b69be2d	Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

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.

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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

Used primarily as an anti-inflammatory agent in the treatment of inflammatory bowel disease as well as for rheumatoid arthritis.

Minimum Risk Level

Not Available

Health Effects

Sulfasalazine in rare cases can cause severe depression in young males. Immune thrombocytopenia has been reported. [Wikipedia]

Symptoms

Not Available

Treatment

Gastric 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

External Links

DrugBank ID

DB00795

HMDB ID

HMDB0014933

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID