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Sulfasalazine information


Sulfasalazine
Clinical data
Trade namesAzulfidine, Salazopyrin, Sulazine, others
Other namesSulphasalazine, SSZ
AHFS/Drugs.comMonograph
MedlinePlusa682204
License data
  • US DailyMed: Sulfasalazine
Pregnancy
category
  • AU: A[1]
Routes of
administration
By mouth
Drug classSulfonamides
ATC code
  • A07EC01 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)[2][3]
  • US: ℞-only
Pharmacokinetic data
Bioavailability<15%
Elimination half-life5-10 hours
Excretiondrug metabolites are excreted in urine and feces [4]
Identifiers
IUPAC name
  • 2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid
CAS Number
  • 599-79-1 checkY
PubChem CID
  • 5339
DrugBank
  • DB00795 checkY
ChemSpider
  • 10481900 checkY
UNII
  • 3XC8GUZ6CB
KEGG
  • D00448 checkY
  • C07316 checkY
ChEBI
  • CHEBI:9334
ChEMBL
  • ChEMBL421 ☒N
CompTox Dashboard (EPA)
  • DTXSID0021256 Edit this at Wikidata
ECHA InfoCard100.009.069 Edit this at Wikidata
Chemical and physical data
FormulaC18H14N4O5S
Molar mass398.39 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point240 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) 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.

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Sulfasalazine

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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...

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Management of ulcerative colitis

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to sulfasalazine characterized by dizziness, fever and skin rash have been reported in a small percentage of patients. In some cases, sulfasalazine can...

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Ulcerative colitis

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maintain remission, including aminosalicylates such as mesalazine or sulfasalazine, steroids, immunosuppressants such as azathioprine, and biologic therapy...

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deficiency. Sulfasalazine, a 5-ASA derivative, is thought to alter adenosine release and inhibit IgE mediated mast cell degranulation, Sulfasalazine is a good...

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Mesalazine

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people who are allergic to aspirin. Mesalazine is the active moiety of sulfasalazine, which is metabolized to sulfapyridine and mesalazine. It is also the...

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Prodrug

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Type II Extracellular Type IIA GI fluids Loperamide oxide, oxyphenisatin, sulfasalazine Type IIB Systemic circulation and other extracellular fluid compartments...

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Aminosalicylate

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includes among others: 4-Aminosalicylic acid Balsalazide Olsalazine Sulfasalazine Mesalazine (5-Aminosalicylic acid) Side effects may include abdominal...

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Rheumatoid arthritis

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outcomes overall. The following drugs are considered DMARDs: methotrexate, sulfasalazine, leflunomide, hydroxychloroquine, TNF inhibitors (certolizumab, adalimumab...

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List of sulfonamides

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(anti-glaucoma carbonic anhydrase inhibitor) Probenecid (uricosuric) Sulfasalazine (anti-inflammatory agent and a DMARD) Sumatriptan (antimigraine triptan)...

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and most especially bleomycin Cyclosporin Bromocriptine Ergotamine Sulfasalazine Anthrax vaccines whose primary ingredient is the Anthrax Protective...

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Leflunomide

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(January 2005). "When a DMARD fails, should patients switch to sulfasalazine or add sulfasalazine to continuing leflunomide?". Annals of the Rheumatic Diseases...

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Cheilitis

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Clomipramine, Cyancobalamin, Gold, Methyldopa, Psoralens, Streptomycin, Sulfasalazine and Tetracycline. A condition called "drug-induced ulcer of the lip"...

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SSZ

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code for Santos Air Base in Santos, São Paulo, Brazil Spaceship Zero Sulfasalazine Hyundai Separated Sound Zone Serbian Party Oathkeepers (Srpska stranka...

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Psoriatic arthritis

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molecules such as methotrexate, leflunomide, cyclosporin, azathioprine, and sulfasalazine are used in persistent symptomatic cases without exacerbation. Rather...

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Drug rash with eosinophilia and systemic symptoms

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ibuprofen Sulfa drugs: Dapsone, sulfamethoxazole-trimethoprim combination, sulfasalazine Anticancer drugs: Sorafenib, vismodegib, vemurafenib, imatinib, Other...

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Methotrexate

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sometimes used in combination with other conventional DMARDs, such as sulfasalazine and hydroxychloroquine. Studies and reviews have found that most rheumatoid...

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Sulfhemoglobinemia

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induced, with drugs associated with it including sulphonamides, such as sulfasalazine or sumatriptan. Another possible cause is occupational exposure to sulfur...

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Antiplatelet drug

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leflunomide, hydroxychloroquine, adalimumab, infliximab, etanercept, sulfasalazine, penicillamine, gold, methotrexate, azathioprine, mycophenolate) Drugs...

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Azoospermia

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like hormone/steroid therapy, SSRIs, antibiotics, 5-ASA inhibitors (sulfasalazine), alpha-blockers, 5-alpha-reductase inhibitors, chemotherapeutic agents...

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IARC group 2B

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such as E-glass and '475' glass fibres Sterigmatocystin Streptozotocin Sulfasalazine Sulfallate 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachlorvinphos...

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Sulfapyridine

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later largely superseded by penicillin and other sulfonamides. The drug sulfasalazine is structurally one molecule of mesalamine linked to one molecule of...

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WHO Model List of Essential Medicines

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Dexamethasone Metoclopramide Ondansetron Complementary: Aprepitantα Sulfasalazine Complementary: Hydrocortisoneα Prednisoloneα Senna Oral rehydration...

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Macrocytic anemia

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absorption or metabolism of Vitamin B12 or folate such as methotrexate, sulfasalazine, metformin, anticonvulsant medications (e.g., valproic acid or phenytoin)...

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antibiotic used in large animals sucralfate – treats gastric ulcers sulfasalazine – anti-inflammatory and antirheumatic Telazol – intravenous drug used...

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Thiosulfil Forte Sulfamethoxazole Gantanol Sulfanilimide (archaic) Sulfasalazine Azulfidine Sulfisoxazole Gantrisin Trimethoprim-Sulfamethoxazole (Co-trimoxazole)...

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Triple therapy

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treatments used in Management of HIV/AIDS the combination of methotrexate, sulfasalazine, and hydroxychloroquine used to treat rheumatoid arthritis This disambiguation...

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