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Mesalazine

Catalog No. DB00244 Name DrugBank
CAS Number 89-57-6 Website http://www.ualberta.ca/
M. F. C7H7NO3 Telephone (780) 492-3111
M. W. 153.13538 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 129

SYNONYMS

IUPAC name
5-amino-2-hydroxybenzoic acid
IUPAC Traditional name
mesalazine
Brand Name
Canasa
Asacol
Fisalamine
Salofalk
Asacolitin
Claversal
Lixacol
Mesasal
Pentasa
Rowasa
Synonyms
5-aminosalicylic acid
Mesalamine
5-aminosalicylate
5-ASA

DATABASE IDS

PubChem CID 4075
PubChem SID 46509142
CAS Number 89-57-6

PROPERTIES

Hydrophobicity(logP) 1.2
Solubility 0.84 g/L at 20°C

DETAILS

Description (English)
Item Information
Drug Groups approved
Description An anti-inflammatory agent, structurally related to the salicylates, which is active in inflammatory bowel disease. It is considered to be the active moiety of sulphasalazine. (From Martindale, The Extra Pharmacopoeia, 30th ed)
Indication For the treatment of active ulcerative proctitis.
Pharmacology Mesalazine (INN, BAN), also known as Mesalamine (USAN) or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammation of the digestive tract (Crohn's disease) and mild to moderate ulcerative colitis. Mesalazine is a bowel-specific aminosalicylate drug that is metabolized in the gut and has its predominant actions there, thereby having fewer systemic side effects. As a derivative of salicylic acid, 5-ASA is also an antioxidant that traps free radicals, which are potentially damaging by-products of metabolism.
Toxicity Oral, mouse: LD50 = 3370 mg/kg; Oral, rat: LD50 = 2800 mg/kg; Skin, rabbit: LD50 = >5 gm/kg. There have been no documented reports of serious toxicity in man resulting from massive overdosing with mesalamine. Under ordinary circumstances, mesalazine absorption from the colon is limited.
Affected Organisms
Humans and other mammals
Biotransformation Rapidly and extensively metabolized, mainly to N-acetyl-5-ASA (Ac-5-ASA) in the intestinal mucosal wall and the liver. Ac-5-ASA is further acetylated (deactivated) in at least 2 sites, the colonic epithelium and the liver.
Absorption 20 to 30% absorbed following oral administration. 10 to 35% absorbed from the colon (rectal suppository) - extent of absorption is determined by the length of time the drug is retained in the colon.
Half Life The mean elimination half-life was 5 hours for 5-ASA and six hours for N-acetyl-5-ASA following the initial dose. At steady state, the mean elimination half-life was seven hours for both 5-ASA and N-acetyl-5-ASA.
Protein Binding About 80% of N-Ac-5-ASA is bound to plasma proteins, whereas 40% of mesalamine is protein bound.
Elimination Approximately 28% of the mesalamine in Asacol tablets is absorbed after oral ingestion, leaving the remainder available for topical action and excretion in the feces.
It is excreted mainly by the kidney as N-acetyl-5-aminosalicylic acid.
References
[Link]
External Links
Wikipedia
RxList
PDRhealth

REFERENCES