orlistat   

GtoPdb Ligand ID: 5277

Synonyms: Alli® | tetrahydrolipstatin | THL | Xenical®
orlistat is an approved drug (FDA (1999), EMA (1998))
Compound class: Synthetic organic
Comment: Orlistat is a lipase inhibitor. Lipase targets include gastric and pancreatic lipases, diacylglycerol lipase (DAGL) and αβ-hydrolase 12 (ABHD12) inhibitor. It is used as an anti-obesity drug treatment. At least 18 isomeric forms exist in PubChem.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 24
Topological polar surface area 81.7
Molecular weight 495.39
XLogP 10.26
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCCCCCC(CC1OC(=O)C1CCCCCC)OC(=O)C(CC(C)C)NC=O
Isomeric SMILES CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
InChI InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
InChI Key AHLBNYSZXLDEJQ-FWEHEUNISA-N
No information available.
Summary of Clinical Use
Preventing the absorption of fats from the human diet, thereby reducing caloric intake in obesity. Orlistat is available form pharmacies without a prescription (OTC) in a number of countries, including the United States, European Union member states, and Australia. The OTC formulations are generally supplied in lower doses than those available on prescription.
Mechanism Of Action and Pharmacodynamic Effects
The primary effect of orlistat is local lipase inhibition within the GI tract. The enzymes are inhibited by drug interaction with serine residues within the enzymes' active sites. This renders the target enzymes unable to hydrolyse dietary triglyceride (fat) substrates into absorbable free fatty acids and monoglycerides, and the fats are excreted unchanged.
Pharmacokinetics
Elimination
The primary route of elimination is through the feces.
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