Mesalazine

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Mesalazine
Mesalazine structure.svg
Systematic (IUPAC) name
5-amino-2-hydroxybenzoic acid
Clinical data
Trade namesPentasa, Delzicol, Canasa, Rowasa, Lialda, Apriso, Salofalk
AHFS/Drugs.commonograph
MedlinePlusa688021
Licence dataUS Daily Med:link
Pregnancy cat.B (US)
Legal status-only (US)
Routesoral, rectal
Pharmacokinetic data
Bioavailabilityorally: 20-30% absorbed
rectally: 10-35%
MetabolismRapidly & extensively metabolised intestinal mucosal wall and the liver
Half-life5 hours after initial dose.
At steady state 7 hours
Identifiers
CAS number89-57-6 YesY
ATC codeA07EC02
PubChemCID 4075
IUPHAR ligand2700
DrugBankDB00244
ChemSpider3933 YesY
UNII4Q81I59GXC YesY
KEGGD00377 YesY
ChEBICHEBI:6775 YesY
ChEMBLCHEMBL704 YesY
Chemical data
FormulaC7H7NO3 
Mol. mass153.135 g/mol
 YesY (what is this?)  (verify)
 
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Mesalazine
Mesalazine structure.svg
Systematic (IUPAC) name
5-amino-2-hydroxybenzoic acid
Clinical data
Trade namesPentasa, Delzicol, Canasa, Rowasa, Lialda, Apriso, Salofalk
AHFS/Drugs.commonograph
MedlinePlusa688021
Licence dataUS Daily Med:link
Pregnancy cat.B (US)
Legal status-only (US)
Routesoral, rectal
Pharmacokinetic data
Bioavailabilityorally: 20-30% absorbed
rectally: 10-35%
MetabolismRapidly & extensively metabolised intestinal mucosal wall and the liver
Half-life5 hours after initial dose.
At steady state 7 hours
Identifiers
CAS number89-57-6 YesY
ATC codeA07EC02
PubChemCID 4075
IUPHAR ligand2700
DrugBankDB00244
ChemSpider3933 YesY
UNII4Q81I59GXC YesY
KEGGD00377 YesY
ChEBICHEBI:6775 YesY
ChEMBLCHEMBL704 YesY
Chemical data
FormulaC7H7NO3 
Mol. mass153.135 g/mol
 YesY (what is this?)  (verify)

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[1] and mild-to-moderate Crohn's disease.[2] 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.[3]

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.[3]

Mesalazine is the active moiety of sulfasalazine, which is metabolized to sulfapyridine and mesalazine.[4]

Mesalazine is the active component of the prodrug balsalazide along with the inert carrier molecule 4-aminobenzoyl-beta-alanine.[5]

Side effects[edit]

Commonly:

Uncommonly:

Rarely:

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

Monitoring[edit]

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[edit]

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.[citation needed] It is marketed under a variety of brand names:[citation needed]

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.[citation needed]

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.[citation needed]

References[edit]

  1. ^ Kruis, W.; Schreiber, I.; Theuer, D.; Brandes, J. W.; Schütz, E.; Howaldt, S.; Krakamp, B.; Hämling, J.; Mönnikes, H.; Koop, I.; Stolte, M.; Pallant, D.; Ewald, U. (2001). "Low dose balsalazide (1.5 g twice daily) and mesalazine (0.5 g three times daily) maintained remission of ulcerative colitis but high dose balsalazide (3.0 g twice daily) was superior in preventing relapses". Gut 49 (6): 783–789. doi:10.1136/gut.49.6.783. PMC 1728533. PMID 11709512.  edit
  2. ^ Sandborn WJ, Feagan BG, Lichtenstein GR (October 2007). "Medical management of mild to moderate Crohn's disease: evidence-based treatment algorithms for induction and maintenance of remission". Alimentary Pharmacology & Therapeutics 26 (7): 987–1003. doi:10.1111/j.1365-2036.2007.03455.x. PMID 17877506. Retrieved 2009-12-20. 
  3. ^ a b "mesalazine". PharmGKB.
  4. ^ Lippencott's Illustrated Reviews: Pharmacology, 4th Ed. Finkel, Cubeddu and Clark
  5. ^ Drugs & Therapy Properties 2003 Oct; Vol 19, No. 10
  6. ^ "Lialda Side Effects & Safety Information". Shire US. October 2007. Retrieved 2008-01-07. 
  7. ^ "Desensitization after fever induced by mesalazine". December 2001. Retrieved 2001-12-24. 

External links[edit]