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.^[5] It is considered by some to be a first-line treatment in rheumatoid arthritis.^[6] It is taken by mouth or can be administered rectally.^[5]

Significant side effects occur in about 25% of people.^[6] Commonly these include loss of appetite, nausea, headache, and rash.^[5] Severe side effects include bone marrow suppression, liver problems, Stevens–Johnson syndrome, and kidney problems.^[6]^[7]^[4] It should not be used in people allergic to aspirin or sulfonamide.^[6] Use during pregnancy appears to be safe for the baby.^[5]

Sulfasalazine is in the disease-modifying antirheumatic drugs (DMARDs) family of medications.^[5] It is unclear exactly how it works.^[5] One proposed mechanism is the inhibition of prostaglandins, resulting in local anti-inflammatory effects in the colon.^[4] The medication is broken down by intestinal bacteria into sulfapyridine and 5-aminosalicylic acid.^[5]

Sulfasalazine was approved for medical use in the United States in 1950.^[5] It is on the World Health Organization's List of Essential Medicines.^[8] Sulfasalazine is available as a generic medication.^[5] In 2020, it was the 284th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[9]^[10]

^ "Sulfasalazine Use During Pregnancy". Drugs.com. 9 November 2018. Retrieved 24 January 2020.
^ "Sulfasalazine 250mg/5ml Oral Suspension - Summary of Product Characteristics (SmPC)". electronic medicines compendium (emc). 13 September 2019. Retrieved 4 December 2019.
^ Cite error: The named reference UKlabel2014 was invoked but never defined (see the help page).
^ ^a ^b ^c Vallerand AH, Sanoski CA, Deglin JH (5 June 2014). Davis's drug guide for nurses (Fourteenth ed.). Philadelphia. ISBN 978-0-8036-4085-6. OCLC 881473728.{{cite book}}: CS1 maint: location missing publisher (link)
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Sulfasalazine". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
^ ^a ^b ^c ^d World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 41, 45. hdl:10665/44053. ISBN 9789241547659.
^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 464. ISBN 9781284057560.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
^ "Sulfasalazine - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.