Sibutramine

Sibutramine, formerly sold under the brand name Meridia among others, is an appetite suppressant which has been discontinued in many countries. It works as a serotonin–norepinephrine reuptake inhibitor similar to a tricyclic antidepressant. Until 2010, it was widely marketed and prescribed as an adjunct in the treatment of obesity along with diet and exercise. It has been associated with increased cardiovascular diseases and strokes and has been withdrawn from the market in 2010 in several countries and regions including Australia, Canada, China, the European Union, Hong Kong, India, Mexico, New Zealand, the Philippines, Thailand, the United Kingdom, and the United States. However, the drug remains available in some countries.

Sibutramine
Sibutramine (top),
(S)-(−)-sibutramine (bottom)
Clinical data
Trade namesMeridia, others
Other namesBTS-54524
AHFS/Drugs.comMonograph
MedlinePlusa601110
Pregnancy
category
  • AU: C
  • No human data exists; inconclusive evidence of teratogenic potential in animal studies
Routes of
administration		Oral (capsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityAbsorption 77%, considerable first-pass metabolism
Protein binding97%, (94% for its desmethyl metabolites, M1 & M2)
MetabolismHepatic (CYP3A4-mediated)
Elimination half-life1 hour (sibutramine), 14 hours (M1) & 16 hours (M2)
ExcretionUrine (77%), feces (8%)
Identifiers
  • 1-(1-(4-chlorophenyl)cyclobutyl)-N,N,2,2-tetramethylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.130.097
Chemical and physical data
FormulaC17H26ClN
Molar mass279.85 g·mol−1
3D model (JSmol)
  • ClC1=CC=C(C2(CCC2)C(CC(C)C)N(C)C)C=C1
  • InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3 Y
  • Key:UNAANXDKBXWMLN-UHFFFAOYSA-N Y
  (verify)

Sibutramine was originally developed in 1988 by Boots in Nottingham, UK, and manufactured and marketed by Abbott Laboratories and sold under a variety of brand names including Reductil, Meridia, Siredia, and Sibutrex before its withdrawal 2010 from most markets. It was classified as a Schedule IV controlled substance in the United States.

As of 2018, the FDA still found sibutramine in over 700 diet supplements marketed as "natural", "traditional" or "herbal remedies".

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