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QuickView for Sibutramine (compound)

Name: sibutramine
PubChem Compound ID: 5210
Molecular formula: C17H26ClN
Molecular weight: 279.848 g/mol
Reductil; Sibutraminum [Latin]; DEA No. 1675; KBio2_002508; Cyclobutanemethanamine, 1-(4-chlorophenyl)-N,N-dimethyl-alpha-(2-methylpropyl)-; Spectrum3_001009; Sibutramine; KBio3_001957; Spectrum2_001686; 84485-00-7.
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Name: sibutramine
Name (isomeric): DB01105
Drug Type: small molecule
Sibutraminum [Latin]; Sibutramina [Spanish]
Brand: Butramin, Meridia, Medaria, Reductil
Category: Anorexigenic Agents, Antidepressants, Appetite Depressants, Stimulants, Antidepressive Agents
CAS number: 106650-56-0
Indication: For the treatment of obesity.
Sibutramine is an orally administered agent for the treatment of obesity. Sibutramine exerts its pharmacological actions predominantly via its secondary (M1) and primary (M2) amine metabolites. The parent compound, sibutramine, is a potent inhibitor of serotonin and norepinephrine reuptake in vivo, but not in vitro. However, metabolit...
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Mechanism of Action:
Sibutramine produces its therapeutic effects by inhibition of norepinephrine (NE), serotonin (5-hydroxytryptamine, 5-HT), and to a lesser extent, dopamine reuptake at the neuronal synapse. By inhibiting the reuptake of these neurotransmitters, sibutramine promotes a sense of satiety and decrease in appetite, thereby reducing food intake. Data from ...
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Absorption: Rapid absorption following oral administration. Absolute bioavailability is not known, but at least 77% of a single oral dose of sibutramine is absorbed.
Protein binding: 97% (to human plasma proteins)
Biotransformation: Hepatic
Route of elimination: Sibutramine is metabolized in the liver principally by the cytochrome P450 (3A4) isoenzyme, to desmethyl metabolites, M1 and M2. These active metabolites are further metabolized by hydroxylation and conjugation to pharmacologically inactive metabolites, M5 and M6. Approximately 85% (range 68-95%) of a single orally administered radiolabeled dose was excreted in urine and feces over a 15-day collection period with the majority of the dose (77%) excreted in the urine. The primary route of excretion for M1 and M2 is hepatic metabolism and for M5 and M6 is renal excretion.
Half Life: 1.1 hours
Clearance: Oral cl=1750 L/h [oral administration]
Toxicity: Side effects include dry mouth, anorexia, insomnia, constipation and headache.
Affected organisms: Humans and other mammals
Drug interaction:
DoxepinIncreased risk of CNS adverse effects
EscitalopramRisk of serotoninergic syndrome
AlmotriptanIncreased risk of CNS adverse effects
TelithromycinTelithromycin may reduce clearance of Sibutramine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Sibutramine if Telithromycin is initiated, discontinued or dose changed.
DextromethorphanCombination associated with possible serotoninergic syndrome
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