Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H53NO5 |
Molecular Weight | 495.7359 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCC[C@@]([H])(C[C@@]1([H])[C@]([H])(CCCCCC)C(=O)O1)OC(=O)[C@]([H])(CC(C)C)N=CO
InChI
InChIKey=AHLBNYSZXLDEJQ-FWEHEUNISA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11249520Curator's Comment:: Description was created based on several sources, including
http://www.fda.gov/downloads/UCM205349.pdf
https://www.ncbi.nlm.nih.gov/pubmed/9225172
https://www.ncbi.nlm.nih.gov/pubmed/16956313
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11249520
Curator's Comment:: Description was created based on several sources, including
http://www.fda.gov/downloads/UCM205349.pdf
https://www.ncbi.nlm.nih.gov/pubmed/9225172
https://www.ncbi.nlm.nih.gov/pubmed/16956313
Orlistat or tetrahydrolipstatin (Xenical, Hoffmann-La Roche) is a saturated derivative of lipstatin originally isolated from Streptomyces toxytricini. Orlistat (Xenical, Hoffmann-La Roche) is a powerful inhibitor of gastrointestinal lipase and as such, reduces fat absorption. Orlistat acts by binding covalently to the serine residue of the active site of gastric and pancreatic lipases. When administered with fat-containing foods, orlistat partially inhibits hydrolysis of triglycerides, thus reducing the subsequent absorption of monoaclglycerides and free fatty acids. Unlike other weight-reducing drugs it is minimally absorbed and has no effects in the CNS. Xenical is indicated for obesity management including weight loss and weight maintenance when used in conjunction witha reduced-calorie diet. XENICAL is also indicated to reduce the risk for weight regain after prior weight loss. XENICAL is
indicated for obese patients with an initial body mass index (BMI) ≥ 30 kg/m2 or ≥ 27 kg/m2 in the presence of other risk factors (eg,
hypertension, diabetes, dyslipidemia).
In addition to its well established efficacy in achieving modest weight loss, orlistat has been shown to improve glycaemic parameters in obese adults with type 2 diabetes mellitus as well as some features of the metabolic syndrome.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11249520
Curator's Comment:: Orlistat is minimally absorbed and has no effects in the CNS
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1812 |
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Target ID: CHEMBL4158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15026345 |
100.0 nM [Ki] | ||
Target ID: CHEMBL1796 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: http://www.fda.gov/downloads/UCM205349.pdf |
Primary | XENICAL Approved UseXENICAL orlistat capsule is indicated for obesity management including weight loss and weight maintenance when used in conjunction with a reduced-calorie diet. XENICAL is also indicated to reduce the risk for weight regain after prior weight loss. XENICAL is indicated for obese patients with an initial body mass index (BMI) ≥30 kg/m2 or ≥27 kg/m2 in the presence of other risk factors (eg, hypertension, diabetes, dyslipidemia). Launch Date9.2482562E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
150 ng × eq/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973989 |
360 mg single, oral dose: 360 mg route of administration: Oral experiment type: SINGLE co-administered: |
ORLISTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
907 ng × eq × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973989 |
360 mg single, oral dose: 360 mg route of administration: Oral experiment type: SINGLE co-administered: |
ORLISTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5 h |
ORLISTAT plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
ORLISTAT plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
5160 mg single, oral Overdose |
healthy, 28 months n = 1 Health Status: healthy Age Group: 28 months Sex: F Population Size: 1 Sources: |
|
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
healthy, 51 years (range: 30-65 year) n = 33 Health Status: healthy Age Group: 51 years (range: 30-65 year) Sex: M+F Population Size: 33 Sources: |
Disc. AE: Fatigue... AEs leading to discontinuation/dose reduction: Fatigue (1 patient) Sources: |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
healthy, 52 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 52 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Disc. AE: Rectal oily spotting, Flatus... AEs leading to discontinuation/dose reduction: Rectal oily spotting (1 patient) Sources: Flatus (1 patient) Abdominal pain (1 patient) Painful defaecation (1 patient) |
180 mg 1 times / day steady, oral Dose: 180 mg, 1 times / day Route: oral Route: steady Dose: 180 mg, 1 times / day Sources: |
healthy, 53 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 53 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Disc. AE: Loose stools, Myocardial infarction... AEs leading to discontinuation/dose reduction: Loose stools (2 patients) Sources: Myocardial infarction (1 patient) |
60 mg 3 times / day steady, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: steady Dose: 60 mg, 3 times / day Sources: |
healthy, 54 years n = 1 Health Status: healthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Disc. AE: Fatigue, Weakness generalized... AEs leading to discontinuation/dose reduction: Fatigue Sources: Weakness generalized Nausea Jaundice Pruritus Hepatic failure |
90 mg 1 times / day steady, oral Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
healthy, 55 years (range: 30-65 year) n = 33 Health Status: healthy Age Group: 55 years (range: 30-65 year) Sex: M+F Population Size: 33 Sources: |
Disc. AE: Loose stools... AEs leading to discontinuation/dose reduction: Loose stools (2 patients) Sources: |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
healthy, adult n = 1913 Health Status: healthy Age Group: adult Population Size: 1913 Sources: |
Disc. AE: Gastrointestinal symptom NOS... AEs leading to discontinuation/dose reduction: Gastrointestinal symptom NOS (8.8%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fatigue | 1 patient Disc. AE |
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
healthy, 51 years (range: 30-65 year) n = 33 Health Status: healthy Age Group: 51 years (range: 30-65 year) Sex: M+F Population Size: 33 Sources: |
Abdominal pain | 1 patient Disc. AE |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
healthy, 52 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 52 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Flatus | 1 patient Disc. AE |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
healthy, 52 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 52 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Painful defaecation | 1 patient Disc. AE |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
healthy, 52 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 52 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Rectal oily spotting | 1 patient Disc. AE |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
healthy, 52 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 52 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Myocardial infarction | 1 patient Disc. AE |
180 mg 1 times / day steady, oral Dose: 180 mg, 1 times / day Route: oral Route: steady Dose: 180 mg, 1 times / day Sources: |
healthy, 53 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 53 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Loose stools | 2 patients Disc. AE |
180 mg 1 times / day steady, oral Dose: 180 mg, 1 times / day Route: oral Route: steady Dose: 180 mg, 1 times / day Sources: |
healthy, 53 years (range: 30-65 year) n = 35 Health Status: healthy Age Group: 53 years (range: 30-65 year) Sex: M+F Population Size: 35 Sources: |
Fatigue | Disc. AE | 60 mg 3 times / day steady, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: steady Dose: 60 mg, 3 times / day Sources: |
healthy, 54 years n = 1 Health Status: healthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Hepatic failure | Disc. AE | 60 mg 3 times / day steady, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: steady Dose: 60 mg, 3 times / day Sources: |
healthy, 54 years n = 1 Health Status: healthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Jaundice | Disc. AE | 60 mg 3 times / day steady, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: steady Dose: 60 mg, 3 times / day Sources: |
healthy, 54 years n = 1 Health Status: healthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Nausea | Disc. AE | 60 mg 3 times / day steady, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: steady Dose: 60 mg, 3 times / day Sources: |
healthy, 54 years n = 1 Health Status: healthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Pruritus | Disc. AE | 60 mg 3 times / day steady, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: steady Dose: 60 mg, 3 times / day Sources: |
healthy, 54 years n = 1 Health Status: healthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Weakness generalized | Disc. AE | 60 mg 3 times / day steady, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: steady Dose: 60 mg, 3 times / day Sources: |
healthy, 54 years n = 1 Health Status: healthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Loose stools | 2 patients Disc. AE |
90 mg 1 times / day steady, oral Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
healthy, 55 years (range: 30-65 year) n = 33 Health Status: healthy Age Group: 55 years (range: 30-65 year) Sex: M+F Population Size: 33 Sources: |
Gastrointestinal symptom NOS | 8.8% Disc. AE |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
healthy, adult n = 1913 Health Status: healthy Age Group: adult Population Size: 1913 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Orlistat. | 2000 Mar-Apr |
|
Orlistat: in the prevention and treatment of type 2 diabetes mellitus. | 2001 |
|
Evidence for specific ceramidase present in the intestinal contents of rats and humans. | 2001 Aug |
|
Primary care diabetes. What options are there? | 2001 Dec |
|
Bulimia nervosa and misuse of orlistat: two case reports. | 2001 Dec |
|
[Changes in lipid profile and paraoxonase activity in obese patients as a result of orlistat treatment]. | 2001 Dec 16 |
|
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection. | 2001 Jan-Mar |
|
Incorrect use and limited weight reduction of orlistat (Xenical) in clinical practice. A cohort study. | 2001 Jul |
|
Current methods used for defining, measuring, and treating obesity. | 2001 Nov |
|
The effects of orlistat on weight and on serum lipids in obese patients with hypercholesterolemia: a randomized, double-blind, placebo-controlled, multicentre study. | 2001 Nov |
|
[Inhibitors of absorption as anti-obesity drugs]. | 2001 Nov |
|
Interaction between orlistat and antihypertensive drugs. | 2001 Nov |
|
Lipoprotein lipase mediates an increase in selective uptake of HDL-associated cholesteryl esters by cells in culture independent of scavenger receptor BI. | 2001 Nov |
|
Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats. | 2001 Nov |
|
[Application for exemption concerning Xenical was refused without explanation]. | 2001 Nov 7 |
|
Drug treatment of obesity. | 2001 Oct |
|
Orlistat inhibits dietary cholesterol absorption. | 2001 Oct |
|
Principles for enhanced recruitment of subjects in a large clinical trial. the XENDOS (XENical in the prevention of Diabetes in Obese Subjects) study experience. | 2001 Oct |
|
[Therapy of obesity. Setting realistic goals]. | 2001 Oct 18 |
|
About orlistat. | 2001 Sep |
|
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function. | 2001 Sep |
|
Weighing the options in the pharmacotherapy of obesity. | 2001 Sep |
|
Pathophysiology and treatment of the dyslipidemia of insulin resistance. | 2001 Sep |
|
[Weight reduction. Antiobesity drug treatment in type-2 diabetics]. | 2002 |
|
[Six-month xenical (orlistat) therapy of patients with stable angina pectoris concomitant with obesity and hyperlipidemia]. | 2002 |
|
[Orlistat. A treatment of limited value for obese persons]. | 2002 Apr |
|
Roche turns to DM to boost patient compliance with its weight loss drug. | 2002 Apr |
|
The cerebrospinal fluid/serum leptin ratio during pharmacological therapy for obesity. | 2002 Apr |
|
Orlistat: its current status as an anti-obesity drug. | 2002 Apr 12 |
|
Biosynthetic precursors of the lipase inhibitor lipstatin. | 2002 Apr 5 |
|
Effects of lipoprotein lipase on uptake and transcytosis of low density lipoprotein (LDL) and LDL-associated alpha-tocopherol in a porcine in vitro blood-brain barrier model. | 2002 Aug 9 |
|
Orlistat: a second look. At best, a minor adjunct to dietary measures. | 2002 Feb |
|
Impact of orlistat therapy on weight reduction in morbidly obese patients after implantation of the Swedish adjustable gastric band. | 2002 Feb |
|
A health economic model to assess the long-term effects and cost-effectiveness of orlistat in obese type 2 diabetic patients. | 2002 Feb |
|
The effect of orlistat on plasma levels of psychotropic drugs in patients with long-term psychopharmacotherapy. | 2002 Feb |
|
Are soft tissue composition of bone and non-bone pixels in spinal bone mineral measurements by DXA similar? Impact of weight loss. | 2002 Jan |
|
Minor long-term changes in weight have beneficial effects on insulin sensitivity and beta-cell function in obese subjects. | 2002 Jan |
|
Evaluation of the safety and efficacy of sibutramine, orlistat and metformin in the treatment of obesity. | 2002 Jan |
|
Usefulness of Orlistat in the treatment of severe hypertriglyceridemia. | 2002 Jan 15 |
|
[Treatment in the community health centers in accordance with recommendations of the Medical Products Agency. Unsatisfactory weight reduction with orlistat]. | 2002 Jan 31 |
|
[Are drugs necessary in the treatment of obesity?]. | 2002 Jan-Feb |
|
Constipation, polyuria, polydipsia, and edema associated with orlistat. | 2002 Jul-Aug |
|
Combining behavioral and pharmacological treatments for obesity. | 2002 Jun |
|
Additive gastrointestinal effects with concomitant use of olestra and orlistat. | 2002 Jun |
|
Can drugs help you lose weight? | 2002 Mar |
|
Orlistat misuse in bulimia nervosa. | 2002 Mar |
|
[Anti-obesity drugs: sibutramine and orlistat]. | 2002 Mar 30 |
|
Serine and threonine beta-lactones: a new class of hepatitis A virus 3C cysteine proteinase inhibitors. | 2002 Mar 8 |
|
Obesity in transplant patients: case report showing interference of orlistat with absorption of cyclosporine and review of literature. | 2002 Mar-Apr |
|
Orlistat in the treatment of Type 2 diabetes mellitus. | 2002 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.fda.gov/downloads/UCM205349.pdf
The recommended dose of XENICAL (orlistat capsule) is one 120-mg capsule three times a day with each main meal containing fat (during or up to 1 hour after the meal).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27188391
Orlistat inhibited cell proliferation by 61 % in ECC-1 cells and 57 % in KLE cells at a dose of 500 μM
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000009916
Created by
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WHO-ATC |
A08AB01
Created by
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EMA ASSESSMENT REPORTS |
ALLI (AUTHORIZED: OBESITY)
Created by
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NCI_THESAURUS |
C29715
Created by
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EMA ASSESSMENT REPORTS |
XENICAL (AUTHORIZED: OBESITY)
Created by
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NDF-RT |
N0000175591
Created by
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WHO-VATC |
QA08AB01
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LIVERTOX |
714
Created by
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7556
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1996
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C29303
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6318
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1478800
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SUB09460MIG
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3034010
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CHEMBL175247
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ORLISTAT
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5277
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C055122
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96829-58-2
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37925
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M8234
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95M8R751W8
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96829-58-2
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DB01083
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Orlistat
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)