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Mesalazine

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(Redirected from 5-Aminosalicylic acid)

Mesalazine
Clinical data
Trade namesAsacol, Lialda, Pentasa, Delzicol, others[1]
Other namesmesalamine, 5-aminosalicylic acid, 5-ASA, Mesalamine (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa688021
License data
Pregnancy
category
Routes of
administration
By mouth, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityorally: 20–30% absorbed
rectally: 10–35%
MetabolismRapidly & extensively metabolized intestinal mucosal wall and the liver
Elimination half-life5 hours after initial dose.
At steady state 7 hours
Identifiers
  • 5-Amino-2-hydroxybenzoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.745 Edit this at Wikidata
Chemical and physical data
FormulaC7H7NO3
Molar mass153.137 g·mol−1
3D model (JSmol)
Melting point283 °C (541 °F)
  • O=C(O)c1cc(ccc1O)N
  • InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11) checkY
  • Key:KBOPZPXVLCULAV-UHFFFAOYSA-N checkY
  (verify)

Mesalazine, also known as mesalamine or 5-aminosalicylic acid (5-ASA), is a medication used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease.[1] It is generally used for mildly to moderately severe disease.[1] It is taken by mouth or rectally.[1] The formulations which are taken by mouth appear to be similarly-effective.[12]

Common side-effects include headache, nausea, abdominal pain, and fever.[1] Serious side-effects may include pericarditis, liver problems, and kidney problems.[1][12] Use in pregnancy and breastfeeding appears safe.[12] In people with a sulfa allergy certain formulations may result in problems.[1] Mesalazine is an aminosalicylate and anti-inflammatory.[1][12] It works by direct contact with the intestines.[1]

Mesalazine was approved for medical use in the United States in 1987.[1][8] It is on the World Health Organization's List of Essential Medicines.[13] It is available as a generic medication.[1][14][15][16] In 2021, it was the 239th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[17][18]

Medical uses

[edit]

It is used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease (effective only in colonic diseases).[1]

In 2022 Germany introduced guidance to use mesalamine to treat acute uncomplicated diverticulitis.[19]

Side-effects

[edit]

Most often reported side-effects are gastrointestinal (GI) (but may also include headache), including: nausea, diarrhea, and abdominal pain.[7]

Very rarely, use of mesalazine has been associated with an exacerbation of the symptoms of colitis, Stevens Johnson syndrome, and erythema multiforme.[7]

Pregnancy

[edit]

There is no data on use in pregnant women, but the drug does cross the placenta and is excreted in breast milk. The drug should not be used in children under two years of age,[7] people with kidney disease,[7] or people who are allergic to aspirin.[7]

Chemistry

[edit]

Mesalazine is the active moiety of sulfasalazine, which is metabolized to sulfapyridine and mesalazine.[20] It is also the active component of the prodrug balsalazide along with the inert carrier molecule 4-aminobenzoyl-beta-alanine.[21] It is in the category of disease-modifying antirheumatic drugs (DMARDs) family of medications.[22] It is unclear exactly how it works.[22] Mesalazine is claimed to be a PPAR-γ agonist.[23]

Mechanism of action

[edit]

Exact mechanism of mesalazine is unknown, but is speculated that mesalazine decreases synthesis of prostaglandin and leukotriene, modulating the inflammatory response derived from the cyclooxygenase and lipooxygenase pathways.[24] It appears to act locally on colonic mucosa.[25]

Society and culture

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Brand names

[edit]

Mesalazine is sold under various names including Apriso, Asacol, Asacol HD, Canasa, Delzicol, Fivasa, Lialda, Salofalk, Pentasa, Rowasa, Octasa, and Sfrowasa. In Europe, it is sold under the name Salofalk (rectal suppository). [26][27]

References

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  1. ^ a b c d e f g h i j k l "Mesalamine Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists.
  2. ^ "Mesalamine Use During Pregnancy". Drugs.com. 18 September 2018. Retrieved 30 December 2019.
  3. ^ "Mesalazine Sun/ Mesalz (Sun Pharma ANZ Pty Ltd)". Therapeutic Goods Administration (TGA). 13 January 2023. Retrieved 9 April 2023.
  4. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  5. ^ "Regulatory Decision Summary for Mezera". Drug and Health Products Portal. 5 February 2024. Retrieved 2 April 2024.
  6. ^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
  7. ^ a b c d e f "Asacol 400mg MR Tablets - Summary of Product Characteristics (SmPC)". (emc). 14 April 2016. Retrieved 30 December 2019.
  8. ^ a b "Asacol HD- mesalamine tablet, delayed release". DailyMed. 15 April 2018. Retrieved 30 December 2019.
  9. ^ "Pentasa- mesalamine capsule". DailyMed. 8 November 2021. Retrieved 17 May 2022.
  10. ^ "Lialda- mesalamine tablet, delayed release". DailyMed. 8 November 2021. Retrieved 17 May 2022.
  11. ^ Human Medicines Evaluation Division (15 October 2020). "Active substance: mesalazine" (PDF). List of nationally authorised medicinal products. European Medicines Agency.
  12. ^ a b c d British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 39–41. ISBN 9780857113382.
  13. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  14. ^ "ANDA Approval Reports - 2017 First Generic Drug Approvals". Food and Drug Administration (FDA). 3 November 2018. Retrieved 8 April 2019.
  15. ^ "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
  16. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  17. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  18. ^ "Mesalamine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  19. ^ Peery AF (12 November 2022). "New German guidelines for the management of diverticulitis". United European Gastroenterology Journal. 10 (9): 913–914. doi:10.1002/ueg2.12331. PMC 9731652. PMID 36302089.
  20. ^ Finkel R, Clark MA, Cubeddu LX (2009). Lippincott's Illustrated Reviews: Pharmacology (Fourth ed.). Lippincott Williams & Wilkins. ISBN 978-0-7817-7155-9.
  21. ^ "Balsalazide: increasing the choice for patients with ulcerative colitis". Drugs & Therapy Perspectives. 19 (1–4): 1–4. 2003. doi:10.2165/00042310-200319100-00001. S2CID 195230977.
  22. ^ a b "Sulfasalazine". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  23. ^ Cevallos SA, Lee JY, Velazquez EM, Foegeding NJ, Shelton CD, Tiffany CR, et al. (January 2021). Ehrt S (ed.). "5-Aminosalicylic Acid Ameliorates Colitis and Checks Dysbiotic Escherichia coli Expansion by Activating PPAR-γ Signaling in the Intestinal Epithelium". mBio. 12 (1): e03227–20. doi:10.1128/mBio.03227-20. PMC 7845635. PMID 33468700.
  24. ^ Nakashima J, Preuss CV (2022). "Mesalamine (USAN)". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 31869178. Retrieved 1 September 2022.
  25. ^ Iacucci M, de Silva S, Ghosh S (February 2010). "Mesalazine in inflammatory bowel disease: a trendy topic once again?". Canadian Journal of Gastroenterology. 24 (2): 127–133. doi:10.1155/2010/586092. PMC 2852235. PMID 20151072.
  26. ^ "Substance Name: Mesalamine [USAN:USP]". ChemIDplus. Retrieved 2 October 2020.
  27. ^ "Mesalamine Uses, Side Effects & Warnings". Drugs.com. 30 August 2019. Retrieved 2 October 2020.