3028 Sibutramine Sibutramine (trade name Meridia in the USA, Reductil in Europe and other countries), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. It is a centrally acting stimulant chemically related to amphetamines. Sibutramine is classified as a Schedule IV controlled substance in the United States. In October 2010, Sibutramine was withdrawn from Canadian and U.S. markets due to concerns that the drug increases the risk of heart attack and stroke in patients with a history of heart disease. 106650-56-0 5210 C17H26ClN 279.175380 White powder. 191-192°C 2.9 mg/mL (in pH 5.2 water) Rapid absorption following oral administration. Absolute bioavailability is not known, but at least 77% of a single oral dose of sibutramine is absorbed. 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 animal studies also suggest that sibutramine may also increase energy expenditure through thermogenic effects in both the basal and fed states, but this has not been confirmed in humans. Sibutramine and its major pharmacologically active metabolites (M1 and M2) do not act via release of monoamines. 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 No indication of carcinogenicity to humans (not listed by IARC). For the treatment of obesity. Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion. Side effects include dry mouth, anorexia, insomnia, constipation and headache. Treatment should consist of general measures employed in the management of overdosage: an airway should be established as needed; cardiac and vital sign monitoring is recommended; general symptomatic and supportive measures should be instituted. Cautious use of p-blockers may be indicated to control elevated blood pressure or tachycardia. (L1712) 2009-07-21T20:28:23Z 2026-05-14T16:57:52Z Sibutramine C07247 458192 Sibutramine DB01105 true CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1 C17H26ClN 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 UNAANXDKBXWMLN-UHFFFAOYSA-N 279.848 279.175377544 Exogenous Solid 5.2 HMDB15237 CHEMBL1419 5021 <p>Chris Senanayake, &#8220;Methods of preparing didesmethylsibutramine and other sibutramine derivatives.&#8221; U.S. Patent US20020183554, issued December 05, 2002.</p> CHEM002347 DTXSID1023578 NS00005033 {1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}dimethylamine 3.24 83.9214 32.9023403046818 5 1 0 9.774437990168428 1 2 5.05 -5.47 9.40e-04 g/l