(RS)-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 (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.

Key facts

Drug.Watchedfields: changed
Drug.class: Serotonin–norepinephrine reuptake inhibitor; Anoretic
Drug.verifiedrevid: 464390010
Drug.IUPAC_name: 1-(1-(4-chlorophenyl)cyclobutyl)-N,N,2,2-tetramethylpropan-1-amine
Drug.image: Sibutramine.svg
Drug.image_class: skin-invert-image
Drug.width: 200px
Drug.image2: Sibutramine ball-and-stick model.png
Drug.image_class2: bg-transparent
Drug.width2: 200px
Drug.caption: Sibutramine (top),(S)-(−)-sibutramine (bottom)
Drug.tradename: Meridia, others
Drug.MedlinePlus: a601110
Drug.pregnancy_AU: C
Drug.pregnancy_US: C
Drug.pregnancy_category: No human data exists; inconclusive evidence of teratogenic potential in animal studies
Drug.legal_BR: B2
Drug.legal_CA_comment: Withdrawn from market

via Wikipedia infobox

Chemical data

Formula: C17H26ClN
Molecular weight: 279.8 g/mol
IUPAC name: 1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine
SMILES: CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N(C)C
InChIKey: UNAANXDKBXWMLN-UHFFFAOYSA-N
XLogP: 5.4
Polar surface area: 3.2 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Research

2 papers

Anorexic effect of (R)-sibutramine: comparison with (RS)-sibutramine [corrected] and (S)-sibutramine.Indian journal of physiology and pharmacology · 2007
Enantioselective behavioral effects of sibutramine metabolites.European journal of pharmacology · 2000

via PubMed

~14 min read

Encyclopedic overview

14 sections

Contents

Medical uses
Contraindications
Side effects
Interactions
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
Detection in body fluids
History
Regulatory approval, 1997–2010
Counterfeit weight-loss products, 2008–present
References
External links

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.

Excerpted from Wikipedia’s “(RS)-sibutramine” article, available under the CC BY-SA 4.0 licence.

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