Product Name

Mesalazine

CAS Number

89-57-6

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Product Name:
Mesalazine
CAS Number:
89-57-6
Indication:
For the treatment of active ulcerative proctitis.
Mode of Action:

Although the mechanism of action of mesalazine is not fully understood, it appears to be topical rather than systemic. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes and hydroxyeicosatetraenoic acids, is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalazine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin production in the colon.

Pharmacodynamics:

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.

Metabolism:

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.

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.

IUPAC:
5-amino-2-hydroxybenzoic acid
ATC:
A07EC02
PubChem:
4075
DrugBank:
DB00244 (APRD01098)
Formula:
C20H22N8O5
Molecular Mass:
153.1354
Synonyms:
5-aminosalicylate 5-aminosalicylic acid 5-ASA Mesalamine
SMILES:
NC1=CC(C(O)=O)=C(O)C=C1
AHFS Code:
56:36.0
General Reference:
General Reference:

  1. Link

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