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Mesalazine

From Wikipedia, the free encyclopedia
Anti-inflammatory medication
Not to be confused withAspirin, also known as acetylsalicylic acid (ASA).

Pharmaceutical compound
Mesalazine
Above: molecular structure of mesalazineBelow: 3D representation of a mesalazine molecule
Clinical data
Trade namesAsacol, Lialda, Pentasa, Delzicol, others[1]
Other namesMesalamine, 5-aminosalicylic acid, 5-ASA, Mesalamine (USANUS)
AHFS/Drugs.comMonograph
MedlinePlusa688021
License data
Pregnancy
category
Routes of
administration		By mouth,rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 20–30%
Rectal: 10–35%
MetabolismRapidly and extensively metabolized intestinal mucosal wall and the liver
Eliminationhalf-life5 hours after initial dose.
At steady state 7 hours
Identifiers
  • 5-Amino-2-hydroxybenzoic acid
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.745Edit 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 asmesalamine or5-aminosalicylic acid (5-ASA), is a medication used to treatinflammatory bowel disease, includingulcerative colitis andCrohn's disease.[1] It is generally used for mildly to moderately severe disease.[1] It is taken by mouth orrectally.[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 includepericarditis,liver problems, andkidney problems.[1][12] Use inpregnancy andbreastfeeding appears safe.[12] In people with asulfa allergy certain formulations may result in problems.[1] Mesalazine is anaminosalicylate andanti-inflammatory.[1][12] It works by direct contact with theintestines.[1]

Mesalazine was approved for medical use in the United States in 1987.[1][8] It is on theWorld Health Organization's List of Essential Medicines.[13] It is available as ageneric medication.[1][14][15][16] In 2023, it was the 202nd most commonly prescribed medication in the United States, with more than 2 million prescriptions.[17][18]

Medical uses

[edit]
See also:4-Aminosalicylic acid

It is used to treatinflammatory bowel disease, includingulcerative colitis andCrohn's disease (effective only in colonic diseases).[1]

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

Side effects

[edit]

Most often reported side effects areheadache,nausea,diarrhea, andabdominal pain.[7]

Very rarely, use of mesalazine has been associated with an exacerbation of the symptoms ofcolitis,Stevens–Johnson syndrome, anderythema multiforme.[7]

Pregnancy

[edit]

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

Mechanism of action

[edit]

The exact mechanism of mesalazine is unknown, but it is speculated that mesalazine decreases synthesis ofprostaglandin andleukotriene, modulating the inflammatory response derived from thecyclooxygenase andlipooxygenase pathways.[20] It appears to act locally on colonic mucosa.[21] In 2025, mesalazine was reported to bindtubulin and stabilizemicrotubules.[22]

Chemistry

[edit]

Mesalazine is an activemetabolite ofsulfasalazine, which is metabolized tosulfapyridine and mesalazine.[23] It is also the active metabolite of theprodrugsbalsalazide (accompanied by the inert carrier molecule 4-aminobenzoyl-β-alanine[24]) andolsalazine (which is metabolized to two equivalents of mesalazine). It is in the category ofdisease-modifying antirheumatic drugs (DMARDs) family of medications.[25] It is unclear exactly how it works.[25] Mesalazine is claimed to be aPPAR-γ agonist.[26]

Mesalazine has application in the synthesis ofCrisdesalazine,Fendosal [53597-27-6] &Parsalmide [30653-83-9].

Society and culture

[edit]

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).[27][28]

References

[edit]
  1. ^abcdefghijkl"Mesalamine Monograph for Professionals".Drugs.com. American Society of Health-System Pharmacists.
  2. ^"Mesalamine Use During Pregnancy".Drugs.com. 18 September 2018. Retrieved30 December 2019.
  3. ^"Mesalazine Sun/ Mesalz (Sun Pharma ANZ Pty Ltd)".Therapeutic Goods Administration (TGA). 13 January 2023. Retrieved9 April 2023.
  4. ^"Product monograph brand safety updates".Health Canada. February 2024. Retrieved24 March 2024.
  5. ^"Regulatory Decision Summary for Mezera".Drug and Health Products Portal. 5 February 2024. Retrieved2 April 2024.
  6. ^"Drug and medical device highlights 2018: Helping you maintain and improve your health".Health Canada. 14 October 2020. Retrieved17 April 2024.
  7. ^abcdef"Asacol 400mg MR Tablets - Summary of Product Characteristics (SmPC)".(emc). 14 April 2016. Retrieved30 December 2019.
  8. ^ab"Asacol HD- mesalamine tablet, delayed release".DailyMed. 15 April 2018. Retrieved30 December 2019.
  9. ^"Pentasa- mesalamine capsule".DailyMed. 8 November 2021. Retrieved17 May 2022.
  10. ^"Lialda- mesalamine tablet, delayed release".DailyMed. 8 November 2021. Retrieved17 May 2022.
  11. ^Human Medicines Evaluation Division (15 October 2020)."Active substance: mesalazine"(PDF).List of nationally authorised medicinal products. European Medicines Agency.
  12. ^abcdBritish 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. Archived fromthe original on 25 April 2018. Retrieved8 April 2019.
  15. ^"2022 First Generic Drug Approvals".U.S.Food and Drug Administration (FDA). 3 March 2023. Archived fromthe original on 30 June 2023. Retrieved30 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. Retrieved29 June 2023.
  17. ^"The Top 300 of 2023".ClinCalc.Archived from the original on 12 August 2025. Retrieved12 August 2025.
  18. ^"Mesalamine - Drug Usage Statistics, United States, 2014 - 2023".ClinCalc. Retrieved17 August 2025.
  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. ^Nakashima J, Preuss CV (2022)."Mesalamine (USAN)".StatPearls. Treasure Island (FL): StatPearls Publishing.PMID 31869178. Retrieved1 September 2022.
  21. ^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.
  22. ^Baksheeva VE, La Rocca R, Allegro D, Derviaux C, Pasquier E, Roche P, et al. (2025). "NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights".Journal of Medicinal Chemistry acs.jmedchem.5c01008.doi:10.1021/acs.jmedchem.5c01008.
  23. ^Finkel R, Clark MA, Cubeddu LX (2009).Lippincott's Illustrated Reviews: Pharmacology (Fourth ed.). Lippincott Williams & Wilkins.ISBN 978-0-7817-7155-9.
  24. ^"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.
  25. ^ab"Sulfasalazine". The American Society of Health-System Pharmacists.Archived from the original on 21 December 2016. Retrieved8 December 2016.
  26. ^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: e03227–20.doi:10.1128/mBio.03227-20.PMC 7845635.PMID 33468700.
  27. ^"Substance Name: Mesalamine [USAN:USP]".ChemIDplus. Retrieved2 October 2020.
  28. ^"Mesalamine Uses, Side Effects & Warnings".Drugs.com. 30 August 2019. Retrieved2 October 2020.
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