Sulfasalazine

Sulfasalazine
Clinical data
Trade namesAzulfidine, Salazopyrin, Sulazine, others
Other namesSulphasalazine, SSZ
AHFS/Drugs.comMonograph
MedlinePlusa682204
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classSulfonamides
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability<15%
Elimination half-life5-10 hours
Excretiondrug metabolites are excreted in urine and feces [4]
Identifiers
  • 2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.069 Edit this at Wikidata
Chemical and physical data
FormulaC18H14N4O5S
Molar mass398.39 g·mol−1
3D model (JSmol)
Melting point240 to 245 °C (464 to 473 °F) (dec.)
  • C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N=NC3=CC(=C(C=C3)O)C(=O)O
  • 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) checkY
  • Key:NCEXYHBECQHGNR-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

  1. ^ "Sulfasalazine Use During Pregnancy". Drugs.com. 9 November 2018. Retrieved 24 January 2020.
  2. ^ "Sulfasalazine 250mg/5ml Oral Suspension - Summary of Product Characteristics (SmPC)". electronic medicines compendium (emc). 13 September 2019. Retrieved 4 December 2019.
  3. ^ Cite error: The named reference UKlabel2014 was invoked but never defined (see the help page).
  4. ^ 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)
  5. ^ 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.
  6. ^ 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.
  7. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 464. ISBN 9781284057560.
  8. ^ 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.
  9. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  10. ^ "Sulfasalazine - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.