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QuickView for Orlistat (compound)

Name: orlistat
PubChem Compound ID: 11092253
Molecular formula: C29H53NO5
Molecular weight: 495.735 g/mol
Name: orlistat
Name (isomeric): DB01083
Drug Type: small molecule
Orlipastat; Tetrahydrolipstatin; (-)-Tetrahydrolipstatin; Orlipastatum [INN-Latin]
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.
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:
Take with meals, or upto 1 hour after a meal. If patient misses a meal, or has a fat-free meal, he/she may skip the corresponding dose.
Drug interaction:
CholecalciferolOrlistat may decrease the serum concentration of Vitamin D analogs. More specifically, orlistat may impair absorption of Vitamin D analogs such as cholecalciferol. Monitor clinical response (plasma calcium concentrations) to orally administered vitamin D analogs closely if used with orlistat. When this combination must be used, consider administering the vitamin D analog at least 2 hours before or after the administration of orlistat.
AnisindioneOrlistat may increase the anticoagulant effect of anisindione.
Vitamin EOrlistat may impair the absorption of vitamin E, a fat soluble vitamin. Oral vitamin E should be administered 2 hours prior to or post orlistat administration.
WarfarinOrlistat may increase the anticoagulant effect of warfarin.
AcenocoumarolOrlistat may increase the anticoagulant effect of acenocoumarol.
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