Sulfasalazine

Sulfasalazine
Clinical data
Trade names	Azulfidine, Salazopyrin, Sulazine, others
Other names	Sulphasalazine, SSZ
AHFS/Drugs.com	Monograph
MedlinePlus	a682204
License data	US DailyMed: Sulfasalazine;
Pregnancy; category	AU: A;
Routes of; administration	By mouth
Drug class	Sulfonamides
ATC code	A07EC01 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	<15%
Elimination half-life	5-10 hours
Excretion	drug metabolites are excreted in urine and feces
Identifiers
	IUPAC name 2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid;
CAS Number	599-79-1 ;
PubChem CID	5339;
DrugBank	DB00795 ;
ChemSpider	10481900 ;
UNII	3XC8GUZ6CB;
KEGG	D00448 ; C07316 ;
ChEBI	CHEBI:9334;
ChEMBL	ChEMBL421 ;
CompTox Dashboard (EPA)	DTXSID0021256 ;
ECHA InfoCard	100.009.069
Chemical and physical data
Formula	C18H14N4O5S
Molar mass	398.39 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	240 to 245 °C (464 to 473 °F) (dec.)
	SMILES C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N=NC3=CC(=C(C=C3)O)C(=O)O;
	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) ; Key:NCEXYHBECQHGNR-UHFFFAOYSA-N ;
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Sulfasalazine, sold under the brand name Azulfidine among others, is a medication used to treat rheumatoid arthritis, ulcerative colitis, and Crohn's disease. It is considered by some to be a first-line treatment in rheumatoid arthritis. It is taken by mouth or can be administered rectally.

Significant side effects occur in about 25% of people. Commonly these include loss of appetite, nausea, headache, and rash. Severe side effects include bone marrow suppression, liver problems, Stevens–Johnson syndrome, and kidney problems. It should not be used in people allergic to aspirin or sulfonamide. Use during pregnancy appears to be safe for the baby.

Sulfasalazine is in the disease-modifying antirheumatic drugs (DMARDs) family of medications. It is unclear exactly how it works. One proposed mechanism is the inhibition of prostaglandins, resulting in local anti-inflammatory effects in the colon. The medication is broken down by intestinal bacteria into sulfapyridine and 5-aminosalicylic acid.

Sulfasalazine was approved for medical use in the United States in 1950. It is on the World Health Organization's List of Essential Medicines. Sulfasalazine is available as a generic medication. In 2020, it was the 284th most commonly prescribed medication in the United States, with more than 1 million prescriptions.