{"ATC Code":"A - Alimentary tract and metabolism","Abbreviation":"","Aliases":["Medaria","Butramin","Sibutramina","(+/-)-Sibutramine","racemic sibutramine","Cf-alli","Sibutraminum","Smr000238156","S-Sibutramine","BTS 54 524"],"Biological Half-Life":"1.1 hours","CAS":"106650-56-0","ChEBI":"CHEBI:9137","ChEMBL":"CHEMBL1419","ChemicalClasses":["amphetamine"],"Chirality":"racemic","Classes":["Stimulant"],"DEA no":1675,"Decomposition":"When heated to decomposition, material emits very toxic fumes of /hydrogen chloride/ and /nitrogen oxides/.  Emits toxic fumes","Dosing Info":[],"Drug Classes":"Breast Feeding; Lactation; Appetite Depressants; Anti-Obesity Agents","Drug Indication":"For the treatment of obesity.","Drug Warnings":"Pregnancy risk category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./","DrugClasses":["depressant","antidepressant"],"EliminationHalfLife":"1 hour (sibutramine), 14 hours (M\u003csub\u003e1\u003c/sub\u003e) \u0026 16 hours (M\u003csub\u003e2\u003c/sub\u003e)","European Community (EC) Number":"600-761-4","FDA Pharmacological Classification":"WV5EC51866","FullSalts":["Sibutramine hydrochloride","Sibutramine mesylate","Sibutramine maleate"],"HMDB ID":"HMDB0015237","HeavyAtomCount":19,"Human Drugs":"Breast Feeding; Lactation; Appetite Depressants; Anti-Obesity Agents","IUPACName":"1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine","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","InChIKey":"UNAANXDKBXWMLN-UHFFFAOYSA-N","MeSH Pharmacological Classification":"Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)","Melting Point":"191-192 °C","MolecularFormula":"C\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eClN","MolecularWeight":"279.8 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"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 \u003ci\u003ein vivo\u003c/i\u003e, but not \u003ci\u003ein vitro\u003c/i\u003e. However, metabolites M1 and M2 inhibit the reuptake of these neurotransmitters both \u003ci\u003ein vitro\u003c/i\u003e and \u003ci\u003ein vivo\u003c/i\u003e. In human brain tissue, M1 and M2 also inhibit dopamine reuptake \u003ci\u003ein vitro\u003c/i\u003e, but with ~3-fold lower potency than for the reuptake inhibition of serotonin or norepinephrine. Sibutramine, M1 and M2 exhibit no evidence of anticholinergic or antihistaminergic actions. In addition, receptor binding profiles show that sibutramine, M1 and M2 have low affinity for serotonin (5-HT\u003csub\u003e1\u003c/sub\u003e, 5-HT\u003csub\u003e1A\u003c/sub\u003e, 5-HT\u003csub\u003e1B\u003c/sub\u003e, 5-HT\u003csub\u003e2A\u003c/sub\u003e, 5-HT\u003csub\u003e2C\u003c/sub\u003e), norepinephrine (b, b1, b3, a1 and a2), dopamine (D1 and D2), benzodiazepine, and glutamate (NMDA) receptors. These compounds also lack monoamine oxidase inhibitory activity \u003ci\u003ein vitro\u003c/i\u003e and \u003ci\u003ein vivo\u003c/i\u003e.","Physical Description":"Solid","PrevSalts":["hydrochloride","mesylate","maleate"],"PubChemId":5210,"Record Description":["Sibutramine is an organochlorine compound and a tertiary amino compound. It has a role as an anti-obesity agent and a serotonin uptake inhibitor.","Sibutramine is a DEA Schedule IV controlled substance. Substances in the DEA Schedule IV have a low potential for abuse relative to substances in Schedule III. It is a Stimulants substance.","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 thus it 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.","Sibutramine is a Norepinephrine, Serotonin, and Dopamine Reuptake Inhibitor Anorectic. The mechanism of action of sibutramine is as a Dopamine Uptake Inhibitor, and Norepinephrine Uptake Inhibitor, and Serotonin Uptake Inhibitor. The physiologic effect of sibutramine is by means of Appetite Suppression.","Sibutramine is a serotonin and norepinephrine reuptake inhibitor which has been used for short- and long-term therapy of obesity, but which was withdrawn from use in the United States in 2010 because of increased risk of cardiovascular events. In large clinical trials, sibutramine therapy was not associated with serum enzyme elevations, and it has only rarely been implicated in cases of clinically apparent, acute liver injury.","SIBUTRAMINE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1997 and is indicated for obesity and has 1 investigational indication. It was withdrawn in at least one region.","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.","See also: Sibutramine Hydrochloride (annotation moved to).","Sibutramine is an organochlorine compound and a tertiary amino compound. It has a role as an anti-obesity agent and a serotonin uptake inhibitor.","LiverTox|Weight loss agent|Obesity|SNRI"],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Sibutramine","Name":"Sibutramine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q424151","Name":"Sibutramine","Sub":false},{"Link":"https://www.wikidata.org/wiki/Q27254858","Name":"(+)-Sibutramine","Sub":true},{"Link":"https://www.wikidata.org/wiki/Q27292614","Name":"(-)-Sibutramine","Sub":true}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01105","Name":"Sibutramine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5210","Name":"Sibutramine","Sub":false},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/667542","Name":"(+)-Sibutramine","Sub":true},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/937011","Name":"(-)-Sibutramine","Sub":true}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1419","Name":"Sibutramine","Sub":false},{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL4582428","Name":"(-)-Sibutramine","Sub":true}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9137","Name":"Sibutramine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=106650-56-0","Name":"Sibutramine","Sub":false},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=154752-44-0","Name":"(+)-Sibutramine","Sub":true},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=153341-22-1","Name":"(-)-Sibutramine","Sub":true}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0015237","Name":"Sibutramine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07247","Name":"Sibutramine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/WV5EC51866","Name":"Sibutramine","Sub":false},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/2K5E83H3LL","Name":"(+)-Sibutramine","Sub":true},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/WFW97V6HV0","Name":"(-)-Sibutramine","Sub":true}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID1023578","Name":"Sibutramine","Sub":false},{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID601316882","Name":"(+)-Sibutramine","Sub":true},{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID501317106","Name":"(-)-Sibutramine","Sub":true}]}],"SMILES":"CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N(C)C","Salts":["hydrochloride","mesylate","maleate"],"SaltsAcidCount":[1,0,1],"SaltsAmineCount":[1,1,1],"SaltsUNII":["OGM0YHD1WF","NTF6Z4MEY2","FL7VAZ52GY"],"Scheduling":[{"gov":"Brazil","schedule":"B2 substance"},{"gov":"United States","schedule":"Schedule IV substance"}],"Solubility":"9.40e-04 g/L","StereoisomerRacemic":"(RS)-Sibutramine","Stereoisomers":["(+)-Sibutramine","(-)-Sibutramine"],"StereoisomersUNII":["2K5E83H3LL","WFW97V6HV0"],"StoreUNII":["WV5EC51866"],"StructureBase64":"PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHhtbG5zOnhsaW5rPSJodHRwOi8vd3d3LnczLm9yZy8xOTk5L3hsaW5rIiBoZWlnaHQ9Ijc0LjM1Mm1tIiB2ZXJzaW9uPSIxLjIiIHZpZXdCb3g9IjAgMCA4MC4wMTEgNzQuMzUyIiB3aWR0aD0iODAuMDExbW0iPgogICAgICAKICAgIDxkZXNjPkdlbmVyYXRlZCBieSB0aGUgQ2hlbWlzdHJ5IERldmVsb3BtZW50IEtpdCAoaHR0cDovL2dpdGh1Yi5jb20vY2RrKTwvZGVzYz4KICAgICAgCiAgICA8ZyBmaWxsPSIjMUZGMDFGIiBzdHJva2U9IiMwMDAwMDAiIHN0cm9rZS1saW5lY2FwPSJyb3VuZCIgc3Ryb2tlLWxpbmVqb2luPSJyb3VuZCIgc3Ryb2tlLXdpZHRoPSIuNyI+CiAgICAgICAgICAgIAogICAgICAgIDxyZWN0IGZpbGw9IiNGRkZGRkYiIGhlaWdodD0iNzUuMCIgc3Ryb2tlPSJub25lIiB3aWR0aD0iODEuMCIgeD0iLjAiIHk9Ii4wIi8+CiAgICAgICAgICAgIAogICAgICAgIDxnIGNsYXNzPSJtb2wiIGlkPSJtb2wxIj4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDEiIHgxPSIxMi40MzQiIHgyPSIyNy42NzQiIHkxPSIxNC4yMzYiIHkyPSIxNC4yMzYiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDIiIHgxPSIyNy42NzQiIHgyPSIzNS4yOTQiIHkxPSIxNC4yMzYiIHkyPSIxLjAzOCIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMyIgeDE9IjI3LjY3NCIgeDI9IjM1LjI5NCIgeTE9IjE0LjIzNiIgeTI9IjI3LjQzNSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kNCIgeDE9IjM1LjI5NCIgeDI9IjUwLjUzNCIgeTE9IjI3LjQzNSIgeTI9IjI3LjQzNSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kNSIgeDE9IjUwLjUzNCIgeDI9IjU4LjE1NCIgeTE9IjI3LjQzNSIgeTI9IjQwLjYzMyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kNiIgeDE9IjU4LjE1NCIgeDI9IjY1Ljc3NCIgeTE9IjQwLjYzMyIgeTI9IjUzLjgzMSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kNyIgeDE9IjY1Ljc3NCIgeDI9Ijc4Ljk3MyIgeTE9IjUzLjgzMSIgeTI9IjQ2LjIxMSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kOCIgeDE9Ijc4Ljk3MyIgeDI9IjcxLjM1MyIgeTE9IjQ2LjIxMSIgeTI9IjMzLjAxMyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kOSIgeDE9IjU4LjE1NCIgeDI9IjcxLjM1MyIgeTE9IjQwLjYzMyIgeTI9IjMzLjAxMyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTAiIHgxPSI1OC4xNTQiIHgyPSI0NC45NTYiIHkxPSI0MC42MzMiIHkyPSI0OC4yNTMiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxnIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDExIj4KICAgICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgICAgICA8bGluZSB4MT0iNDQuOTU2IiB4Mj0iMzEuNzUzIiB5MT0iNDguMjUzIiB5Mj0iNDAuNjI0Ii8+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjQyLjUxOCIgeDI9IjMxLjc1MyIgeTE9IjQ5LjY2IiB5Mj0iNDMuNDQiLz4KICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8L2c+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxMiIgeDE9IjMxLjc1MyIgeDI9IjE4LjU1NSIgeTE9IjQwLjYyNCIgeTI9IjQ4LjI0NCIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGcgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTMiPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIxOC41NTUiIHgyPSIxOC41NiIgeTE9IjQ4LjI0NCIgeTI9IjYzLjQ5MyIvPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIyMC45OTQiIHgyPSIyMC45OTgiIHkxPSI0OS42NTIiIHkyPSI2Mi4wODUiLz4KICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8L2c+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxNCIgeDE9IjE4LjU2IiB4Mj0iMzEuNzYzIiB5MT0iNjMuNDkzIiB5Mj0iNzEuMTIxIi8+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8ZyBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxNSI+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjMxLjc2MyIgeDI9IjQ0Ljk2MSIgeTE9IjcxLjEyMSIgeTI9IjYzLjUwMSIvPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIzMS43NjMiIHgyPSI0Mi41MjIiIHkxPSI2OC4zMDUiIHkyPSI2Mi4wOTQiLz4KICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8L2c+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxNiIgeDE9IjQ0Ljk1NiIgeDI9IjQ0Ljk2MSIgeTE9IjQ4LjI1MyIgeTI9IjYzLjUwMSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTciIHgxPSIxOC41NiIgeDI9IjYuODc1IiB5MT0iNjMuNDkzIiB5Mj0iNzAuMjM5Ii8+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxOCIgeDE9IjUwLjUzNCIgeDI9IjU2LjA0IiB5MT0iMjcuNDM1IiB5Mj0iMTcuODk5Ii8+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxOSIgeDE9IjU2LjA0IiB4Mj0iNTAuNTM0IiB5MT0iMTAuNTc0IiB5Mj0iMS4wMzgiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDIwIiB4MT0iNjEuNDk1IiB4Mj0iNzMuMzk0IiB5MT0iMTQuMjM2IiB5Mj0iMTQuMjM2Ii8+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8cGF0aCBjbGFzcz0iYXRvbSIgZD0iTTIuOTA2IDY5LjI5N3EtLjc4NiAuMCAtMS4yMzkgLjUzcS0uNDUyIC41MjQgLS40NTIgMS40NDdxLS4wIC45MSAuNDE3IDEuNDQ2cS40MjIgLjUzIDEuMjY4IC41M3EuMzIxIC4wIC42MDcgLS4wNTRxLjI5MiAtLjA1OSAuNTY1IC0uMTQydi41MzVxLS4yNzMgLjEwMiAtLjU2NSAuMTQ5cS0uMjkyIC4wNTQgLS42OTcgLjA1NHEtLjc0NCAtLjAgLTEuMjUgLS4zMXEtLjUgLS4zMD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Uses":"The U.S. Food and Drug Administration (FDA) is recommending against continued prescribing and use of Meridia (sibutramine) because this drug may pose unnecessary cardiovascular risks to patients. FDA has requested that Abbott Laboratories-the manufacturer of Meridia-voluntarily withdraw this drug product from the United States market. Abbott has agreed to voluntarily stop marketing of Meridia in the United States.  Meridia was FDA-approved in November 1997 for weight loss and maintenance of weight loss in patients with a body mass index (BMI) greater than or equal to 30 (=30) kg/sq m or for patients with a BMI =27 kg/sq m who have other cardiovascular risk factors. BMI is a measure of body fat in adults that is based on height and weight. Patients with a BMI =30 kg/sq m are considered obese.  FDA's recommendation is based on new data from the Sibutramine Cardiovascular Outcomes (SCOUT) trial, which demonstrated a 16% increase in risk of major adverse cardiovascular events (a composite of non-fatal heart attack, non-fatal stroke, resuscitation after cardiac arrest and cardiovascular death) in patients treated with Meridia compared to patients taking a placebo. At the end of the trial (60 months), patients in the Meridia group lost a small amount of body weight compared to patients in the placebo group. FDA has concluded that the risk for an adverse cardiovascular event from Meridia in the population studied outweighed any benefit from the modest weight loss observed with the drug.","Title":"Sibutramine","UNII":"WV5EC51866","Wikidata":"Q424151","Wikipedia":"Sibutramine","XLogP":5.4}