Sulfasalazine

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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
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

by mouth or can be administered rectally.[5]

Significant side effects occur in about 25% of people.

sulfonamide.[6] Use during pregnancy appears to be safe for the baby.[5]

Sulfasalazine is in the

5-aminosalicylic acid.[5]

Sulfasalazine was approved for medical use in the United States in 1950.

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]

Medical uses

Sulfasalazine is used in the treatment of inflammatory bowel disease, including ulcerative colitis and Crohn's disease. It is also indicated for use in rheumatoid arthritis and used in other types of inflammatory arthritis (e.g. psoriatic arthritis and reactive arthritis).[11][3][2]

It is usually not given to children under two years of age.[3][2]

Side effects

Use of sulfasalazine is contraindicated in people with sulfa allergies and in those with urinary tract obstructions, intestinal obstructions, and severe liver or kidney problems.[4]

Sulfasalazine metabolizes to sulfapyridine. Serum levels should be monitored every three months, and more frequently at the outset. Serum levels above 50 μg/L are associated with side effects. In rare cases, sulfasalazine can cause severe depression in young males. It can also cause oligospermia and temporary infertility. Immune thrombocytopenia has been reported.[12]

Sulfasalazine inhibits dihydropteroate synthase, and can cause folate deficiency and megaloblastic anemia.[13][14][15] and various other undesirable effects.[16]

Sulfasalazine can cause

G6PD deficiency.[17]

Sulfasalazine can cause kidney stones.[18] Sulfasalazine may cause stomach upset, nausea, vomiting, loss of appetite, headache, dizziness, or unusual tiredness.[5] Skin and urine can become orange, with occasional allergic reactions.[19][5]

Sulfasalazine may cause sulfhemoglobinemia.[citation needed]

Pharmacology

Around 90% of a dose of sulfasalazine reaches the colon, where most of it is metabolized by bacteria into sulfapyridine and mesalazine (also known as 5-aminosalicylic acid or 5-ASA). Both metabolites are active; most of the sulfapyridine is absorbed and then further metabolized, but most mesalazine is not, and remains in the colon.[3]

A mix of unchanged, hydroxylated, and glucuronidated sulfapyridine is eliminated in urine, as is acetylated mesalazine and unmetabolized sulfasalazine.[3][2]

The mechanism of action is not clear, but it appears that sulfasalazine and its metabolites have

immunosuppressive, antibacterial, and anti-inflammatory effects.[11][3] It also appears to inhibit the cystine-glutamate antiporter,[20] as well as sepiapterin reductase.[21]

Chemistry

It is a

5-aminosalicylic acid
coupled with an azo linkage.

Cost

In people with rheumatoid arthritis, the cost-effectiveness of sulfasalazine is improved by combining it with other drugs.[22] It is commonly used in treating inflammatory bowel disease in part due to its cost effectiveness.[23]

Research

Sulfasalazine has been studied in

urticaria,[26] and amyloidosis.[27]

References

  1. ^ "Sulfasalazine Use During Pregnancy". Drugs.com. 9 November 2018. Retrieved 24 January 2020.
  2. ^ a b c d "Sulfasalazine 250mg/5ml Oral Suspension - Summary of Product Characteristics (SmPC)". electronic medicines compendium (emc). 13 September 2019. Retrieved 4 December 2019.
  3. ^ a b c d e f "Salazopyrin Tablets - Summary of Product Characteristics". electronic medicines compendium (emc). February 2014. Archived from the original on 16 April 2017.
  4. ^
    OCLC 881473728.{{cite book}}: CS1 maint: location missing publisher (link
    )
  5. ^ a b c d e f g h i j k "Sulfasalazine". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  6. ^
    ISBN 9789241547659
    .
  7. ISBN 9781284057560
    .
  8. 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.
  11. ^ a b "Azulfidine- sulfasalazine tablet". DailyMed. 8 May 2019. Archived from the original on 29 October 2015. Retrieved 24 January 2020.
  12. PMID 17551063
    .
  13. ^ Inflammatory Bowel Disease~workup at eMedicine
  14. ^ Women With Autoimmune Diseases: Medications During Pregnancy and Lactation: Sulfasalazine; "Women with Autoimmune Diseases: Medications During Pregnancy and Lactation: Sulfasalazine". Archived from the original on 21 October 2011. Retrieved 8 March 2012.
  15. PMID 11096168
    .
  16. PMID 24844246
    .
  17. ^ "SulfaSALAzine: Drug Information Provided by Lexi-Comp". Merck & Co., Inc. January 2012. Archived from the original on 29 August 2011. Retrieved 28 July 2012.{{cite web}}: CS1 maint: unfit URL (link)
  18. PMID 27012055
    .
  19. ^ "Sulfasalazine". WebMD. Archived from the original on 26 January 2016.
  20. PMID 21564084
    .
  21. PMID 22178186
    .
  22. PMID 22162693
    .
  23. ISBN 978-3-319-33703-6
    .
  24. PMID 15633128
    .
  25. PMID 1690970
    .
  26. PMID 17043190
    .
  27. PMID 26576950
    .
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