Sibutramine

Sibutramine
	Sibutramine (top),; (S)-(−)-sibutramine (bottom)
Clinical data
Trade names	Meridia, others
Other names	BTS-54524
AHFS/Drugs.com	Monograph
MedlinePlus	a601110
Pregnancy; category	AU: C; No human data exists; inconclusive evidence of teratogenic potential in animal studies;
Routes of; administration	By mouth
Drug class	Serotonin–norepinephrine reuptake inhibitor; Anoretic
ATC code	A08AA10 (WHO) ;
Legal status
Legal status	BR: Class B2 (Anorectic drugs); CA: Withdrawn from market; US: Schedule IV;
Pharmacokinetic data
Bioavailability	Absorption 77%, considerable first-pass metabolism
Protein binding	97%, (94% for its desmethyl metabolites, M1 & M2)
Metabolism	Hepatic (CYP3A4-mediated)
Elimination half-life	1 hour (sibutramine), 14 hours (M1) & 16 hours (M2)
Excretion	Urine (77%), feces (8%)
Identifiers
	IUPAC name 1-(1-(4-chlorophenyl)cyclobutyl)-N,N,2,2-tetramethylpropan-1-amine;
CAS Number	106650-56-0 ; 766462-77-5 (chlorosibutramine);
PubChem CID	5210;
IUPHAR/BPS	2586;
DrugBank	DB01105 ;
ChemSpider	5021 ;
UNII	WV5EC51866;
KEGG	D08513 ;
ChEMBL	ChEMBL1419 ;
CompTox Dashboard (EPA)	DTXSID1023578 ;
ECHA InfoCard	100.130.097
Chemical and physical data
Formula	C17H26ClN
Molar mass	279.85 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=CC=C(C2(CCC2)C(CC(C)C)N(C)C)C=C1;
	InChI 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 ; Key:UNAANXDKBXWMLN-UHFFFAOYSA-N ;
	(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 (SNRI) similar to certain antidepressants. Until 2010, it was widely marketed and prescribed as an adjunct in the treatment of obesity along with diet and exercise.

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. It was classified as a Schedule IV controlled substance in the United States.

In 2010, the drug was withdrawn from most markets, including Australia, Canada, China, the European Union, Hong Kong, India, Mexico, New Zealand, the Philippines, Thailand, the United Kingdom, and the United States, after a study associated it with an increased risk of myocardial infarction and ischaemic stroke. However, the drug remains legally available in countries such as Russia, where it is available only by prescription exclusively to adults, and Brazil. It has also continued to circulate in the form of counterfeit weight-loss products, including dietary and herbal supplements.