Repositioning Candidate Details
| Candidate ID: | R0323 |
| Source ID: | DB01083 |
| Source Type: | approved; investigational |
| Compound Type: | small molecule |
| Compound Name: | Orlistat |
| Synonyms: | |
| Molecular Formula: | C29H53NO5 |
| SMILES: | CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O |
| Structure: |
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| DrugBank Description: | Orlistat is a drug used in the treatment of obesity. Its primary function is preventing the absorption of fats from the human diet, thereby reducing caloric intake. Orlistat works by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine. Without this enzyme, triglycerides from the diet are prevented from being hydrolyzed into absorbable free fatty acids and are excreted undigested. |
| CAS Number: | 96829-58-2 |
| Molecular Weight: | 495.7348 |
| DrugBank 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. |
| DrugBank 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, fat from the diet is excreted undigested and not absorbed by the body. Because some vitamins are fat soluble, the effect of orlistat is to reduce their body absorption. Therefore the drug should only be taken in conjuction with fatty meals, and a multivitamin tablet containing these vitamins (D E K and beta-carotene) should be taken once a day, at least 2 hours before or after taking the drug. In the March 15, 2004 issue of Cancer Research, [1] Steven J. Kridel <i>et al.</i> state that orlistat may also inhibit growth of prostate cancer, and in theory may be useful in treating other cancers, by interfering with the metabolism of fats. |
| DrugBank MoA: | 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 fatty acids and monoglycerides. As undigested triglycerides are not absorbed, the resulting caloric deficit may have a positive effect on weight control. |
| Targets: | Pancreatic triacylglycerol lipase; Gastric triacylglycerol lipase; Fatty acid synthase |
| Inclusion Criteria: |
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