Structure via PubChem · Public domain (PubChem)
orlistat
Sign in to saveAlso 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 Ų
- 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
- Subclass of
- lactone
- Has part
- carbon
- Mass
- 495.392374
- Has use
- medication
Show 10 more facts
- found in taxon
- Camellia sinensis
- chemical formula
- C₂₉H₅₃NO₅
- World Health Organisation international non-proprietary name
- orlistat
- medical condition treated
- obesity
- 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
- subject has role
- anti-obesity medication
- physically interacts with
- pancreatic lipase
via Wikidata · CC0
~11 min read
Encyclopedic overview
18 sectionsContents
- 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, 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.
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.
Excerpted from Wikipedia’s “orlistat” article, available under the CC BY-SA 4.0 licence.
Gallery (3)
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