Structure via PubChem · Public domain (PubChem)
mesalazine
Sign in to saveAlso known as 5-aminosalicylic acid, 5-ASA, Pentasa®, 3-carboxy-4-hydroxyaniline, m-Aminosalicylic acid, 5-Aminosalicylate, Mesalazina
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. It is generally used for mildly to moderately severe disease. It is taken by mouth or rectally. The formulations which are taken by mouth appear to be similarly effective.
Key facts
- Drug.caption
- Above: molecular structure of mesalazine Below: 3D representation of a mesalazine molecule
- Drug.image2
- Mesalazine 3D.png
- Drug.image_class2
- bg-transparent
- Drug.USAN
- Mesalamine
- Drug.tradename
- Asacol, Lialda, Pentasa, Delzicol, others
- Drug.MedlinePlus
- a688021
- Drug.DailyMedID
- Mesalamine
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth, rectal
- Drug.ATC_prefix
- A07
- Drug.ATC_suffix
- EC02
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.bioavailability
- Oral: 20–30% Rectal: 10–35%
- Drug.metabolism
- Rapidly and extensively metabolized intestinal mucosal wall and the liver
via Wikipedia infobox
Chemical data
- Formula
- C7H7NO3
- Molecular weight
- 153.14 g/mol
- IUPAC name
- 5-amino-2-hydroxybenzoic acid
- SMILES
- C1=CC(=C(C=C1N)C(=O)O)O
- InChIKey
- KBOPZPXVLCULAV-UHFFFAOYSA-N
- XLogP
- 1.3
- Polar surface area
- 83.6 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
5,878 papers- Mesalazine-induced eosinophilic pneumonia.Respiration; international review of thoracic diseases · 1999
- [Mesalazine-induced myocarditis].Nihon Shokakibyo Gakkai zasshi = The Japanese journal of gastro-enterology · 2020
- [Mesalazine renal lithiasis.].Archivos espanoles de urologia · 2020
- Mesalazine for the treatment of inflammatory bowel disease.Expert opinion on pharmacotherapy · 2013
- Systematic review: safety of mesalazine in ulcerative colitis.Alimentary pharmacology & therapeutics · 2018
via PubMed
Wikidata facts
- Mass
- 153.042593
- Image
- Mesalazine structure.svg
Show 4 more facts
- chemical formula
- C₇H₇NO₃
- canonical SMILES
- C1=CC(=C(C=C1N)C(=O)O)O
- World Health Organisation international non-proprietary name
- mesalazine
- Commons category
- Mesalazine
via Wikidata · CC0
~3 min read
Article
8 sectionsContents
- Medical uses
- Side effects
- Pregnancy
- Mechanism of action
- Chemistry
- Society and culture
- Brand names
- References
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. It is generally used for mildly to moderately severe disease. It is taken by mouth or rectally. The formulations which are taken by mouth appear to be similarly effective.
Common side effects include headache, nausea, abdominal pain, and fever. Serious side effects may include pericarditis, liver problems, and kidney problems. Use in pregnancy and breastfeeding appears safe. In people with a sulfa allergy certain formulations may result in problems. Mesalazine is an aminosalicylate and anti-inflammatory. It works by direct contact with the intestines.