Mesalazine

Mesalazine

Systematic (IUPAC) name
5-amino-2-hydroxybenzoic acid
Clinical data
Trade names	Pentasa, Delzicol, Canasa, Rowasa, Lialda, Apriso, Salofalk
AHFS/Drugs.com	monograph
MedlinePlus	a688021
Licence data	US Daily Med:link
Pregnancy category	US: B (No risk in non-human studies)
Legal status	US: ℞-only
Routes of administration	oral, rectal
Pharmacokinetic data
Bioavailability	orally: 20-30% absorbed rectally: 10-35%
Metabolism	Rapidly & extensively metabolised intestinal mucosal wall and the liver
Biological half-life	5 hours after initial dose. At steady state 7 hours
Identifiers
CAS Number	89-57-6 Y
ATC code	A07EC02 (WHO)
PubChem	CID: 4075
IUPHAR/BPS	2700
DrugBank	DB00244 Y
ChemSpider	3933 Y
UNII	4Q81I59GXC Y
KEGG	D00377 Y
ChEBI	CHEBI:6775 Y
ChEMBL	CHEMBL704 Y
Chemical data
Formula	C7H7NO3
Molecular mass	153.135 g/mol
SMILES O=C(O)c1cc(ccc1O)N
InChI InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11) Y Key:KBOPZPXVLCULAV-UHFFFAOYSA-N Y
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Mesalazine (INN, BAN), also known as mesalamine (USAN) or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammatory bowel disease, such as ulcerative colitis and mild-to-moderate Crohn's disease. Mesalazine is a bowel-specific aminosalicylate drug that acts locally in the gut and has its predominant actions there, thereby having few systemic side effects.

As a derivative of salicylic acid, mesalazine is also thought to be an antioxidant that traps free radicals, which are potentially damaging byproducts of metabolism.

Mesalazine is the active moiety of sulfasalazine, which is metabolized to sulfapyridine and mesalazine.

Mesalazine is the active component of the prodrug balsalazide along with the inert carrier molecule 4-aminobenzoyl-beta-alanine.

Side effects

Commonly:

• Diarrhea
• Nausea
• Cramping
• Flatulence

Uncommonly:

• Headache
• Exacerbation of the colitis
• Hypersensitivity reactions (including rash, urticaria aka hives, interstitial nephritis and lupus erythematosus-like syndrome)
• Hair loss

Rarely:

• Acute pancreatitis
• Hepatitis
• Nephrotic syndrome
• Blood disorders (including agranulocytosis, aplastic anaemia, leukopenia, neutropenia, thrombocytopenia)
• Fever

Mesalazine avoids the sulfonamide side effects of sulfasalazine (which contains additional sulfapyridine), but carries additional rare risks of:

• Allergic lung reactions
• Allergic myocarditis
• Methaemoglobinaemia

Monitoring

As a result of the small risks of kidney, liver and blood disorders, blood tests should be taken before and after starting treatment. Patients are advised to report any unexplained bleeding, bruising, purpura, sore throat, fever or malaise that occurs during treatment so that a full blood count can be urgently taken.

Formulations

Pentasa 250 MG Extended Release Capsule

Mesalazine is formulated for oral ingestion as tablets or granules, and for rectal administration as a rectal suppository, suspension or enemas. It is marketed under a variety of brand names:

• UK: Asacol, Ipocal, Pentasa, Salofalk, Mezavant XL, Octasa
• Ireland: Asacolon, Pentasa, Salofalk, Mezavant XL
• France: Asacol, Pentasa, Mezavant
• US: Asacol HD, Canasa, Rowasa, Pentasa, Delzicol, Lialda, Apriso, Salofalk
• Spain / España: Pentasa, Claversal, Lixacol, Mezavant, Salofalk
• Canada: Asacol, Pentasa, Salofalk, Mezavant
• India: Mesacol (available as tablets, suppositories, enema), VEGAZ-OD.
• Mexico: Salofalk
• Serbia: Salofalk
• Turkey: Salofalk, Pentasa, Asacol, Encolit
• Uruguay: Mesacron, Mesalazina
• Brazil: Mesalazina, Mesalazina Enema, Mesacol, Mesacol MNX, Asalit,
• Australia: Mesasal, Pentasa, Salofalk, Mezavant (all source PBS)
• Egypt: Pentasa, Salofalk
• Belgium: Dipentum (olsalazine), Pentasa, Colitofalk, Asacol, Mezavant
• The Netherlands: Salofalk, Pentasa, Asacol, Mezavant

Chron-asa 5, Pentasa, Pentasa Enema, Mesaneo

Dosing depends on the preparation used; in particular, slow-release tablets may have quite different drug delivery characteristics and are not interchangeable.

Preparations that lower stool pH (such as lactulose, a laxative) will possibly affect the binding of mesalazine in the bowel and will therefore reduce its efficacy.