orlistat

Also known as tetrahydrolipstatin, THL, (-)-tetrahydrolipstatin

Orlistat, sold under the brand name Xenical among others, is a medication used to treat obesity. Its primary function is preventing the absorption of fats from the human diet by acting as a lipase inhibitor, thereby reducing caloric intake. It is intended for use in conjunction with a healthcare provider-supervised reduced-calorie diet.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 408353644
Drug.image: Orlistat structure.svg
Drug.image_class: skin-invert-image
Drug.width: 300
Drug.image2: Orlistat ball-and-stick model.png
Drug.image_class2: bg-transparent
Drug.width2: 300
Drug.tradename: Xenical, Alli
Drug.MedlinePlus: a601244
Drug.licence_EU: yes
Drug.DailyMedID: Orlistat
Drug.licence_US: Orlistat
Drug.pregnancy_AU: B1
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: A08
Drug.ATC_suffix: AB01

via Wikipedia infobox

Chemical data

Formula: C29H53NO5
Molecular weight: 495.7 g/mol
IUPAC name: [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate
SMILES: CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
InChIKey: AHLBNYSZXLDEJQ-FWEHEUNISA-N
XLogP: 10
Polar surface area: 81.7 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

2,760 papers

Orlistat-associated adverse effects and drug interactions: a critical review.Drug safety · 2008
Orlistat, a new lipase inhibitor for the management of obesity.Pharmacotherapy · 2000
Orlistat.Heart disease (Hagerstown, Md.) · 2000
Low-dose orlistat promotes the therapeutic effect of oxaliplatin in colorectal cancer.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2022
Orlistat.Drugs · 1998

via PubMed

Wikidata facts

Mass: 495.392374

Show 6 more facts

chemical formula: C₂₉H₅₃NO₅
World Health Organisation international non-proprietary name: orlistat
isomeric SMILES: CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
canonical SMILES: CCCCCCCCCCCC(CC1C(C(=O)O1)CCCCCC)OC(=O)C(CC(C)C)NC=O
Commons category: Orlistat
defined daily dose: 0.36

Sources (4)

via Wikidata · CC0

~11 min read

Article

18 sections

Contents

Medical uses
Contraindications
Side effects
Long-term
Precautions
Interactions
Mechanism of action
Legal status
Australia and New Zealand
United States
European Union and Switzerland
Generic formulations
Society and culture
Cost
Counterfeit products
References
Further reading
External links

Orlistat is the saturated derivative of lipstatin, a potent natural inhibitor of pancreatic lipases isolated from the bacterium Streptomyces toxytricini. However, due to its relative simplicity and stability, orlistat was chosen over lipstatin for development as an anti-obesity drug.