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QuickView for mesalamine (compound)
PubChem
| Name: | Mesalamine |
|---|---|
| PubChem Compound ID: | 201587 |
| 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) |
| Molecular formula: | C7H8ClNO3 |
| Molecular weight: | 189.596 g/mol |
| Synonyms: |
89-57-6; 5-Aminosalicylic acid, hydrochloride; AIDS020063; AI3-03745; 5-Aminosalicylic acid hydrochloride; 6291-36-7; AIDS-020063; Benzoic acid, 5-amino-2-hydroxy-, hydrochloride; Salicylic acid, 5-amino-, hydrochloride
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DrugBank
Identification
| Name: | Mesalamine |
|---|---|
| Name (isomeric): | DB00244 |
| Drug Type: | small molecule |
| 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) |
| Synonyms: |
Mesalamine; 5-aminosalicylic acid; 5-ASA; 5-aminosalicylate
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| Brand: | Lixacol, Fisalamine, Rowasa, Claversal, Asacol, Asacolitin, Salofalk, Pentasa, Canasa, Mesasal |
| CAS number: | 89-57-6 |
Pharmacology
| 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, t...
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| Mechanism 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 ...
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| 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. |
| Protein binding: | About 80% of N-Ac-5-ASA is bound to plasma proteins, whereas 40% of mesalamine is protein bound. |
| 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. |
| Route of 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. |
| 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. |
| 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 |
Interactions
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Targets
