Name: | orlistat |
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PubChem Compound ID: | 11092253 |
Molecular formula: | C29H53NO5 |
Molecular weight: | 495.735 g/mol |
Name: | orlistat |
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Name (isomeric): | DB01083 |
Drug Type: | small molecule |
Synonyms: |
Orlipastat; Tetrahydrolipstatin; (-)-Tetrahydrolipstatin; Orlipastatum [INN-Latin]
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Brand: | Alli, Xenical |
Category: | Anti-Obesity Agents, Enzyme Inhibitors |
CAS number: | 96829-58-2 |
Indication: | For obesity management including weight loss and weight maintenance when used in conjunction with a reduced-calorie diet. Also used to reduce the risk for weight regain after prior weight loss. Use of orlistat is pending revision due to reports of liver-related adverse events. |
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Pharmacology: |
Orlistat is a lipase inhibitor for obesity management that acts by
inhibiting the absorption of dietary fats. At the recommended
therapeutic dose of 120 mg three times a day, orlistat inhibits
dietary fat absorption by approximately 30%. It works by inhibiting pancreatic lipase, an enzyme that breaks down fat in the intestine. Without this enzyme, ...
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Mechanism of Action: |
Orlistat is a reversible inhibitor of lipases. It exerts its therapeutic activity in the lumen of the stomach and small intestine by forming a covalent bond with the active serine residue site of gastric and pancreatic lipases. The inactivated enzymes are thus unavailable to hydrolyze dietary fat in the form of triglycerides into absorbable free fa...
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Absorption: | Systemic absorption of orlistat is minimal, however systemic absorption of the drug is not needed for activity. |
Protein binding: | >99% bound to plasma proteins (lipoproteins and albumin were major binding proteins). |
Biotransformation: | Metabolized primarily within the gastrointestinal wall forming relatively inactive metabolites. Metabolites M1 (4-member lactone ring hydrolyzed) and M3 (M1 with N-formyl leucine moiety cleaved) accounted for approximately 42% of total radioactivity in plasma. M1 and M3 have an open beta-lactone ring and extremely weak lipase inhibitory activity (1000- and 2500-fold less than orlistat, respectively). |
Route of elimination: | Following a single oral dose of 360 mg 14C-orlistat in both normal weight and obese subjects, fecal excretion of the unabsorbed drug was found to be the major route of elimination. Orlistat and its M1 and M3 metabolites were also subject to biliary excretion. |
Half Life: | 1 to 2 hours. |
Toxicity: | The results of a massive overdose of Xenical are unknown, although the drug seems relatively harmless. |
Affected organisms: | Humans and other mammals |
Food interaction: |
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Drug interaction: |
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