U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ORLISTAT

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

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/16956313

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

Curator's Comment:: Orlistat is minimally absorbed and has no effects in the CNS

Originator

Curator's Comment:: # Hoffmann-La Roche & Co., Ltd.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
XENICAL

Approved Use

XENICAL 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 Date

924825600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
150 ng × eq/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
907 ng × eq × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
ORLISTAT plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
ORLISTAT plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5160 mg single, oral
Overdose
Dose: 5160 mg
Route: oral
Route: single
Dose: 5160 mg
Sources:
healthy, 28 months
Health Status: healthy
Age Group: 28 months
Sex: F
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)
Health Status: healthy
Age Group: 51 years (range: 30-65 year)
Sex: M+F
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)
Health Status: healthy
Age Group: 52 years (range: 30-65 year)
Sex: M+F
Sources:
Disc. AE: Rectal oily spotting, Flatus...
AEs leading to
discontinuation/dose reduction:
Rectal oily spotting (1 patient)
Flatus (1 patient)
Abdominal pain (1 patient)
Painful defaecation (1 patient)
Sources:
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)
Health Status: healthy
Age Group: 53 years (range: 30-65 year)
Sex: M+F
Sources:
Disc. AE: Loose stools, Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Loose stools (2 patients)
Myocardial infarction (1 patient)
Sources:
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
Health Status: healthy
Age Group: 54 years
Sex: F
Sources:
Disc. AE: Fatigue, Weakness generalized...
AEs leading to
discontinuation/dose reduction:
Fatigue
Weakness generalized
Nausea
Jaundice
Pruritus
Hepatic failure
Sources:
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)
Health Status: healthy
Age Group: 55 years (range: 30-65 year)
Sex: M+F
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
Health Status: healthy
Age Group: adult
Sources:
Disc. AE: Gastrointestinal symptom NOS...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal symptom NOS (8.8%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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)
Health Status: healthy
Age Group: 51 years (range: 30-65 year)
Sex: M+F
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)
Health Status: healthy
Age Group: 52 years (range: 30-65 year)
Sex: M+F
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)
Health Status: healthy
Age Group: 52 years (range: 30-65 year)
Sex: M+F
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)
Health Status: healthy
Age Group: 52 years (range: 30-65 year)
Sex: M+F
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)
Health Status: healthy
Age Group: 52 years (range: 30-65 year)
Sex: M+F
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)
Health Status: healthy
Age Group: 53 years (range: 30-65 year)
Sex: M+F
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)
Health Status: healthy
Age Group: 53 years (range: 30-65 year)
Sex: M+F
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
Health Status: healthy
Age Group: 54 years
Sex: F
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
Health Status: healthy
Age Group: 54 years
Sex: F
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
Health Status: healthy
Age Group: 54 years
Sex: F
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
Health Status: healthy
Age Group: 54 years
Sex: F
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
Health Status: healthy
Age Group: 54 years
Sex: F
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
Health Status: healthy
Age Group: 54 years
Sex: F
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)
Health Status: healthy
Age Group: 55 years (range: 30-65 year)
Sex: M+F
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
Health Status: healthy
Age Group: adult
Sources:
PubMed

PubMed

TitleDatePubMed
Orlistat.
2000 Mar-Apr
Oral hypoglycemic agents: insulin secretagogues, alpha-glucosidase inhibitors and insulin sensitizers.
2001
Pharmacological treatment of obesity in paediatric patients.
2001
Primary care diabetes. What options are there?
2001 Dec
["Xenical doesn't function"--theory and reality].
2001 Dec 12
[Changes in lipid profile and paraoxonase activity in obese patients as a result of orlistat treatment].
2001 Dec 16
Orlistat associated subacute hepatic failure.
2001 Jan
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection.
2001 Jan-Mar
Comparative evaluation of fecal fat excretion induced by orlistat and chitosan.
2001 Jun
Orlistat--a novel weight loss therapy.
2001 Mar
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
[Drugs for obesity. Why are obese patients diferent?].
2001 Nov 3
[Application for exemption concerning Xenical was refused without explanation].
2001 Nov 7
The advances on the knowledge base of obesity and future therapeutic directions.
2001 Sep
About orlistat.
2001 Sep
[Weight reduction. Antiobesity drug treatment in type-2 diabetics].
2002
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
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
Constipation, polyuria, polydipsia, and edema associated with orlistat.
2002 Jul-Aug
Combining behavioral and pharmacological treatments for obesity.
2002 Jun
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
Patents

Sample Use Guides

In Vivo Use Guide
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
Orlistat inhibited cell proliferation by 61 % in ECC-1 cells and 57 % in KLE cells at a dose of 500 μM
Name Type Language
ORLISTAT
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
ORLISTAT [USP-RS]
Common Name English
ORLISTAT [USP MONOGRAPH]
Common Name English
ORLISTAT [MART.]
Common Name English
RO-180647-002
Code English
XENICAL
Brand Name English
ORLISTAT [INN]
Common Name English
RO-18-0647/002
Code English
RO 18-0647/002
Code English
L-LEUCINE, N-FORMYL-, 1-((3-HEXYL-4-OXO-2-OXETANYL)METHYL)DODECYL ESTER, (2S-(2.ALPHA.(R*),3.BETA.))-
Common Name English
ORLISTAT [JAN]
Common Name English
ALLI
Brand Name English
ORLISTAT [USAN]
Common Name English
ORLISTAT [VANDF]
Common Name English
N-FORMYL-L-LEUCINE, ESTER WITH (3S,4S)-3-HEXYL-4-((2S)-2-HYDROXYTRIDECYL)-2-OXETANONE
Common Name English
NSC-758881
Code English
ORLISTAT [ORANGE BOOK]
Common Name English
ORLISTAT [HSDB]
Common Name English
RO-180647002
Code English
ORLISTAT [EMA EPAR]
Common Name English
ORLISTAT [WHO-DD]
Common Name English
ORLISTAT [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000009916
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
WHO-ATC A08AB01
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
EMA ASSESSMENT REPORTS ALLI (AUTHORIZED: OBESITY)
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
NCI_THESAURUS C29715
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
EMA ASSESSMENT REPORTS XENICAL (AUTHORIZED: OBESITY)
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
NDF-RT N0000175591
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
WHO-VATC QA08AB01
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
LIVERTOX 714
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
Code System Code Type Description
HSDB
7556
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
DRUG CENTRAL
1996
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
NCI_THESAURUS
C29303
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
INN
6318
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
USP_CATALOG
1478800
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY USP-RS
EVMPD
SUB09460MIG
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
PUBCHEM
3034010
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL175247
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
WIKIPEDIA
ORLISTAT
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
IUPHAR
5277
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
MESH
C055122
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
EPA CompTox
96829-58-2
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
RXCUI
37925
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M8234
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY Merck Index
FDA UNII
95M8R751W8
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
CAS
96829-58-2
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
DRUG BANK
DB01083
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY
LACTMED
Orlistat
Created by admin on Fri Jun 25 22:10:20 UTC 2021 , Edited by admin on Fri Jun 25 22:10:20 UTC 2021
PRIMARY