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orlistat

Structure via PubChem · Public domain (PubChem)

EntityQ424163· pop 34· linked from 582 articles

orlistat

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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 Ų
H-bond donors
1
H-bond acceptors
5
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
1998
Admin. routes
oral
Indications
polycystic ovary syndrome, obesity, Hyperlipoproteinemia type 1, infertility

via ChEMBL · EBI

Research

2,760 papers

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
Sources (4)

via Wikidata · CC0

~11 min read

Encyclopedic overview

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, 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)

Available in 33 languages

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via Wikidata sitelinks · CC0