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Namespace Prefixes

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Statements

Subject Item
n2:DB01105
rdf:type
n3:Drug
n3:description
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 In October 2010, Sibutramine was withdrawn from Canadian and U.S. markets due to concerns that the drug increases the risk of heart attack and stroke in patients with a history of heart disease.
n3:generalReferences
# Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18671470 # Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19475780 # Heal DJ, Aspley S, Prow MR, Jackson HC, Martin KF, Cheetham SC: Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine. Int J Obes Relat Metab Disord. 1998 Aug;22 Suppl 1:S18-28; discussion S29. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9758240 # Stock MJ: Sibutramine: a review of the pharmacology of a novel anti-obesity agent. Int J Obes Relat Metab Disord. 1997 Mar;21 Suppl 1:S25-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9130038
n3:group
illicit approved withdrawn investigational
n3:halfLife
1.1 hours
n3:indication
For the treatment of obesity.
owl:sameAs
n17:DB01105 n27:DB01105
dcterms:title
Sibutramine
adms:identifier
n7:D08513 n8:0074-2456-12 n10:2586 n11:C07247 n12:2586 n13:5021 n14:DB01105 n18:46507740 n22:PA451344 n23:5210 n29:Sibutramine
n3:mechanismOfAction
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.
n3:packager
n15:271B4029-363D-11E5-9242-09173F13E4C5 n15:271B402A-363D-11E5-9242-09173F13E4C5 n15:271B402D-363D-11E5-9242-09173F13E4C5 n15:271B402E-363D-11E5-9242-09173F13E4C5 n15:271B402B-363D-11E5-9242-09173F13E4C5 n15:271B402C-363D-11E5-9242-09173F13E4C5 n15:271B402F-363D-11E5-9242-09173F13E4C5 n15:271B4030-363D-11E5-9242-09173F13E4C5
n3:patent
n19:5436272
n3:routeOfElimination
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.
n3:synonym
Sibutraminum Sibutramina Butramin
n3:toxicity
Side effects include dry mouth, anorexia, insomnia, constipation and headache.
n24:hasAHFSCode
n28:28-20-92
n3:proteinBinding
97% (to human plasma proteins)
n3:synthesisReference
Chris Senanayake, "Methods of preparing didesmethylsibutramine and other sibutramine derivatives." U.S. Patent US20020183554, issued December 05, 2002.
n4:hasConcept
n5:M0162538
foaf:page
n21:sibutramine.html n31:sibutramine.htm n32:mer1254.shtml
n3:IUPAC-Name
n9:271B4038-363D-11E5-9242-09173F13E4C5
n3:InChI
n9:271B403E-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n9:271B403D-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n9:271B403A-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n9:271B403B-363D-11E5-9242-09173F13E4C5
n3:SMILES
n9:271B403C-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n9:271B404D-363D-11E5-9242-09173F13E4C5 n9:271B4036-363D-11E5-9242-09173F13E4C5
n3:logP
n9:271B4034-363D-11E5-9242-09173F13E4C5 n9:271B404F-363D-11E5-9242-09173F13E4C5 n9:271B4037-363D-11E5-9242-09173F13E4C5
n3:logS
n9:271B4035-363D-11E5-9242-09173F13E4C5
n24:hasATCCode
n25:A08AA10
n3:H-Bond-Acceptor-Count
n9:271B4044-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n9:271B4045-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n9:271B403F-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n9:271B4040-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n9:271B4042-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n9:271B4041-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n9:271B4043-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapid absorption following oral administration. Absolute bioavailability is not known, but at least 77% of a single oral dose of sibutramine is absorbed.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
106650-56-0
n3:category
n3:clearance
* Oral cl=1750 L/h [oral administration]
n3:containedIn
n26:271B4031-363D-11E5-9242-09173F13E4C5 n26:271B4032-363D-11E5-9242-09173F13E4C5 n26:271B4033-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n9:271B4049-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n9:271B404B-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n9:271B404C-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n9:271B404E-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n9:271B4048-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n9:271B4047-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n9:271B404A-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n9:271B4039-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n9:271B4046-363D-11E5-9242-09173F13E4C5