Sibutramine

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 Edit this at Wikidata
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 checkY
  • Key:UNAANXDKBXWMLN-UHFFFAOYSA-N checkY
  (verify)

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 It has been associated with increased cardiovascular diseases and strokes and has been withdrawn from the market in 2010 in several countries and regions including Australia,[2] Canada,[3] China,[4] the European Union,[5] Hong Kong,[6] India,[7] Mexico, New Zealand,[8] the Philippines,[9] Thailand,[10] the United Kingdom,[11] and the United States.[12] However, the drug remains available in some countries.[13]

Sibutramine was originally developed in 1988 by Boots in Nottingham, UK,[14] 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".

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ "Sibutramine (Reductil) - withdrawal in Australia". Therapeutic Goods Administration (Tga). Therapeutic Goods Administration, Department of Health, Australian Government. 2010. Archived from the original on 2014-07-03. Retrieved 2014-10-06.
  3. ^ Health Canada Endorsed Important Safety Information on MERIDIA (Sibutramine Hydrochloride Monohydrate) Archived 2013-01-11 at the Wayback Machine: Subject: Voluntary withdrawal of Meridia (sibutramine) capsules from the Canadian market.
  4. ^ "Notification of Termination of Production, Sale, and Usage of Sibutramine Preparations and Their Active Pharmaceutical Ingredient". sda.gov in People's Republic of China. October 30, 2010. Archived from the original on 2011-10-07. Retrieved 2011-05-21.
  5. ^ (in German) Sibutramin-Vertrieb in der Europäischen Union ausgesetzt [1] Archived 2012-07-19 at archive.today. Abbott Laboratories in Germany. Press Release 2010-01-21. Retrieved 2010-01-27
  6. ^ "De-registration of pharmaceutical products containing sibutramine" (Press release). info.gov in Hong Kong. November 2, 2010. Retrieved 2010-11-08.
  7. ^ "Banned Medicines" (Press release). Ministry of Health and Family Welfare. February 10, 2011. Retrieved 2011-03-15.
  8. ^ "Withdrawal of Sibutramine (Reductil) in New Zealand" (Press release). MedSafe in New Zealand. October 11, 2010. Retrieved 2012-11-06.
  9. ^ "FDA warns online sellers of banned slimming pills". January 12, 2014. Archived from the original on January 15, 2014. Retrieved February 20, 2014.
  10. ^ "Thai FDA reveals voluntary withdrawal of sibutramine from the Thai market" (PDF) (Press release). Food and Drug Administration of Thailand. October 20, 2010. Archived from the original (PDF) on 2011-05-11. Retrieved 2010-12-22.
  11. ^ "Top obesity drug sibutramine being suspended". BBC News. 2010-01-22. Archived from the original on 2010-01-25. Retrieved 2010-01-22.
  12. ^ Rockoff JD, Dooren JC (October 8, 2010). "Abbott Pulls Diet Drug Meridia Off US Shelves". The Wall Street Journal. Archived from the original on 11 October 2010. Retrieved 8 October 2010.
  13. ^ "Sibutramine - Drugs.com". drugs.com. Archived from the original on 2017-10-08. Retrieved 2017-10-08.
  14. ^ Buckett WR, Thomas PC, Luscombe GP (1988). "The pharmacology of sibutramine hydrochloride (BTS 54 524), a new antidepressant which induces rapid noradrenergic down-regulation". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 12 (5): 575–584. doi:10.1016/0278-5846(88)90003-6. PMID 2851857. S2CID 24787523.