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

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H53NO5
Molecular Weight 495.7348
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@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O

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
Molecular Formula C29H53NO5
Molecular Weight 495.7348
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

CNS Non-penetrant
1040
Curator's Comment: Orlistat is minimally absorbed and has no effects in the CNS

Originator

Hoffman-La Roche
135
Curator's Comment: # Hoffmann-La Roche & Co., Ltd.

Approval Year

1999
175
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
 100.0 nM [Ki]
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020766s029lbl.pdf
ORLISTAT plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020766s029lbl.pdf
ORLISTAT plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:94686
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:94686
ChemicalBook
CB2431985
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2431985
eMolecules
593023
https://www.emolecules.com/cgi-bin/more?vid=593023
MolPort
MolPort-005-938-035
https://www.molport.com/shop/molecule-link/MolPort-005-938-035
Selleck Chemicals
Orlistat(Alli)
http://www.selleckchem.com/products/Orlistat(Alli).html
ZINC
ZINC000008214635
http://zinc15.docking.org/substances/ZINC000008214635
PubMed

PubMed

TitleDatePubMed
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.
2002-08-09
Constipation, polyuria, polydipsia, and edema associated with orlistat.
2002-06-28
[Are drugs necessary in the treatment of obesity?].
2002-06-01
Combining behavioral and pharmacological treatments for obesity.
2002-06
Clinical efficacy of orlistat therapy in overweight and obese patients with insulin-treated type 2 diabetes: A 1-year randomized controlled trial.
2002-06
Additive gastrointestinal effects with concomitant use of olestra and orlistat.
2002-06
Demand, appropriateness and prescribing of 'lifestyle drugs': a consultation survey in general practice.
2002-06
Orlistat in the treatment of Type 2 diabetes mellitus.
2002-05
Orlistat: its current status as an anti-obesity drug.
2002-04-12
Obesity in transplant patients: case report showing interference of orlistat with absorption of cyclosporine and review of literature.
2002-04-11
Biosynthetic precursors of the lipase inhibitor lipstatin.
2002-04-05
[Orlistat. A treatment of limited value for obese persons].
2002-04
Roche turns to DM to boost patient compliance with its weight loss drug.
2002-04
Results of obesity treatment.
2002-04
The cerebrospinal fluid/serum leptin ratio during pharmacological therapy for obesity.
2002-04
[Anti-obesity drugs: sibutramine and orlistat].
2002-03-30
Serine and threonine beta-lactones: a new class of hepatitis A virus 3C cysteine proteinase inhibitors.
2002-03-08
Can drugs help you lose weight?
2002-03
Orlistat misuse in bulimia nervosa.
2002-03
Orlistat: a second look. At best, a minor adjunct to dietary measures.
2002-02
Reduction in blood cyclosporine concentration by orlistat in two renal transplant patients.
2002-02
Impact of orlistat therapy on weight reduction in morbidly obese patients after implantation of the Swedish adjustable gastric band.
2002-02
A health economic model to assess the long-term effects and cost-effectiveness of orlistat in obese type 2 diabetic patients.
2002-02
The effect of orlistat on plasma levels of psychotropic drugs in patients with long-term psychopharmacotherapy.
2002-02
[Treatment in the community health centers in accordance with recommendations of the Medical Products Agency. Unsatisfactory weight reduction with orlistat].
2002-01-31
Usefulness of Orlistat in the treatment of severe hypertriglyceridemia.
2002-01-15
Are soft tissue composition of bone and non-bone pixels in spinal bone mineral measurements by DXA similar? Impact of weight loss.
2002-01
Minor long-term changes in weight have beneficial effects on insulin sensitivity and beta-cell function in obese subjects.
2002-01
Evaluation of the safety and efficacy of sibutramine, orlistat and metformin in the treatment of obesity.
2002-01
Obesity.
2002-01
[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
[Changes in lipid profile and paraoxonase activity in obese patients as a result of orlistat treatment].
2001-12-16
["Xenical doesn't function"--theory and reality].
2001-12-12
Orlistat.
2001-12-01
Primary care diabetes. What options are there?
2001-12
Bulimia nervosa and misuse of orlistat: two case reports.
2001-12
American College of Sports Medicine position stand. Appropriate intervention strategies for weight loss and prevention of weight regain for adults.
2001-12
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection.
2001-11-27
[Application for exemption concerning Xenical was refused without explanation].
2001-11-07
[Drugs for obesity. Why are obese patients diferent?].
2001-11-03
Current methods used for defining, measuring, and treating obesity.
2001-11
The effects of orlistat on weight and on serum lipids in obese patients with hypercholesterolemia: a randomized, double-blind, placebo-controlled, multicentre study.
2001-11
[Inhibitors of absorption as anti-obesity drugs].
2001-11
Interaction between orlistat and antihypertensive drugs.
2001-11
Lipoprotein lipase mediates an increase in selective uptake of HDL-associated cholesteryl esters by cells in culture independent of scavenger receptor BI.
2001-11
Drug treatment of obesity.
2001-10
[Obesity and cardiovascular risk].
2001-09
The advances on the knowledge base of obesity and future therapeutic directions.
2001-09
Orlistat: in the prevention and treatment of type 2 diabetes mellitus.
2001
Patents

Patents

04983746
2
08637700
2
JP2001172180A
3
JP2001220387A
1
JP2001509173A
1
JP2002511398A
12
JP2002522491A
1
JP2002522492A
1
JP2002541106A
100
JP2003500451A
2
JP2003509373A
3
JP2003511458A
19
JP2003518129A
11
JP2003518130A
14
JP2003521546A
1
JP2004346078A
1
JP2004505066A
1
JP2004505067A
1
JP2004536047A
26
JP2005531588A
10
JP2006520365A
2
JP2007501823A
1
JP2007501852A
1
JP2007509048A
1
JP2007514770A
77
JP2008120821A
1
JP2009073833A
1
JP2009108062A
1
JP2009108076A
1
JP2009173635A
1
JP2011528275A
456
JP3761783B2
1
JP3774118B2
1
JP4217017B2
1
JP4265911B2
1
JP4365554B2
24
JP4737836B2
1
JP4772264B2
1
JP4851546B2
1
JPH05194471A
1
JPH1066592A
1
JPH11255645A
1

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
In Vitro Use Guide
Orlistat inhibited cell proliferation by 61 % in ECC-1 cells and 57 % in KLE cells at a dose of 500 μM
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:24:56 GMT 2025
Edited
by admin
on Mon Mar 31 21:24:56 GMT 2025
Record UNII
95M8R751W8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORLISTAT
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
ALLI
Preferred Name English
ORLISTAT [USP-RS]
Common Name English
ORLISTAT [USP MONOGRAPH]
Common Name English
ORLISTAT [MART.]
Common Name English
Orlistat [WHO-DD]
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
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 [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000009916
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
WHO-ATC A08AB01
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
EMA ASSESSMENT REPORTS ALLI (AUTHORIZED: OBESITY)
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
NCI_THESAURUS C29715
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
EMA ASSESSMENT REPORTS XENICAL (AUTHORIZED: OBESITY)
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
NDF-RT N0000175591
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
WHO-VATC QA08AB01
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
LIVERTOX NBK548898
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
Code System Code Type Description
HSDB
7556
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
DRUG CENTRAL
1996
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
NSC
758881
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
NCI_THESAURUS
C29303
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
INN
6318
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
DAILYMED
95M8R751W8
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
EVMPD
SUB09460MIG
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
PUBCHEM
3034010
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
ChEMBL
CHEMBL175247
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
WIKIPEDIA
ORLISTAT
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
USAN
DD-13
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
SMS_ID
100000091440
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
IUPHAR
5277
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
MESH
C055122
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
CHEBI
94686
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
RS_ITEM_NUM
1478800
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
EPA CompTox
DTXSID8023395
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
RXCUI
37925
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m8234
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY Merck Index
FDA UNII
95M8R751W8
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
CAS
96829-58-2
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
DRUG BANK
DB01083
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
LACTMED
Orlistat
Created by admin on Mon Mar 31 21:24:56 GMT 2025 , Edited by admin on Mon Mar 31 21:24:56 GMT 2025
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of ORLISTAT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
PANCREATIC TRIACYLGLYCEROL LIPASE
TARGET -> INHIBITOR
IRREVERSIBLE INHIBITOR
Related Record Type Details
Structure of RO-61-0593
METABOLITE -> PARENT
URINE
Structure of 2-HEXYL-3,5-DIHYDROXYDECANEDIOIC ACID, (2S,3R,5S)-
METABOLITE -> PARENT
URINE
Structure of ORLISTAT OPEN RING (S,S)-ISOMER
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of RO-61-0593 GLUCURONIDE
METABOLITE -> PARENT
MAJOR
URINE
Structure of 2-HEXYL-3,5-DIHYDROXYHEXADECANOIC ACID, (2S,3R,5S)-
METABOLITE -> PARENT
MAJOR
PLASMA
Related Record Type Details
Structure of 3-HEXYL-4-((R)-2-HYDROXYTRIDECYL)-2-OXETANONE, (3S,4S)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
USP
Structure of Orlistat, (R,S,S,S)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ORLISTAT HEXYL UNDECYL PYRANONE
IMPURITY -> PARENT
Structure of Triphenylphosphine oxide
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-FORMYL-L-LEUCINE (3S,4R,6S)-3-HEXYL-2-OXO-6-UNDECYLTETRAHYDRO-2H-PYRAN-4-YL ESTER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ORLISTAT HENICOSENYL LEUCINATE
IMPURITY -> PARENT
Structure of ORLISTAT OPEN RING EPIMER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-FORMYLLEUCINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DIISOPROPYL HYDRAZODICARBOXYLATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
Structure of ORLISTAT OPEN RING AMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ORLISTAT OPEN RING ((1R)-1-PHENYL)ETHYLAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ISOLEUCINE ORLISTAT, L-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of ORLISTAT
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966