Mesalazine

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Not to be confused with Aspirin, also known as acetylsalicylic acid (ASA).

Mesalazine
Above: molecular structure of mesalazine Below: 3D representation of a mesalazine molecule
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
BioavailabilityOral: 20–30%
Rectal: 10–35%
MetabolismRapidly and 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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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 2023, it was the 202nd most commonly prescribed medication in the United States, with more than 2 million prescriptions.[17][18]

Medical uses

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See also: 4-Aminosalicylic acid

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

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Most often reported side effects are headache, 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

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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]

Mechanism of action

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The exact mechanism of mesalazine is unknown, but it is speculated that mesalazine decreases synthesis of prostaglandin and leukotriene, modulating the inflammatory response derived from the cyclooxygenase and lipooxygenase pathways.[20] It appears to act locally on colonic mucosa.[21] In 2025, mesalazine was reported to bind tubulin and stabilize microtubules.[22]

Chemistry

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Mesalazine is an active metabolite of sulfasalazine, which is metabolized to sulfapyridine and mesalazine.[23] It is also the active metabolite of the prodrugs balsalazide (accompanied by the inert carrier molecule 4-aminobenzoyl-β-alanine[24]) and olsalazine (which is metabolized to two equivalents of mesalazine). It is in the category of disease-modifying antirheumatic drugs (DMARDs) family of medications.[25] It is unclear exactly how it works.[25] Mesalazine is claimed to be a PPAR-γ agonist.[26]

Society and culture

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Brand names

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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

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