Sibutramine (CHEM002347)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:23 UTC
Update Date2026-05-14 16:57:52 UTC
Accession NumberCHEM002347
Identification
Common NameSibutramine
ClassSmall Molecule
DescriptionSibutramine (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 In October 2010, Sibutramine was withdrawn from Canadian and U.S. markets due to concerns that the drug increases the risk of heart attack and stroke in patients with a history of heart disease.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Anorexigenic Agent
  • Antidepressant
  • Antidepressive Agent
  • Appetite Depressant
  • Drug
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Stimulant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ButraminKegg
MeridiaHMDB
DidesmethylsibutramineHMDB
Sibutramine hydrochlorideHMDB
Di-desmethylsibutramineHMDB
mono-DesmethylsibutramineHMDB
(R)-DDMSHMDB
N-1-(1-(4-Chlorophenyl)cyclobutyl)-3-methylbutyl-N,N-dimethylamine HCLHMDB
ReductilHMDB
Chemical FormulaC17H26ClN
Average Molecular Mass279.848 g/mol
Monoisotopic Mass279.175 g/mol
CAS Registry Number106650-56-0
IUPAC Name{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}dimethylamine
Traditional Namesibutramine
SMILESCC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1
InChI IdentifierInChI=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
InChI KeyUNAANXDKBXWMLN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Aralkylamine
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point191-192°C
Boiling PointNot Available
Solubility2.9 mg/mL (in pH 5.2 water)
Predicted Properties
PropertyValueSource
Water Solubility0.00094 g/LALOGPS
logP5.05ALOGPS
logP5.2ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.92 m³·mol⁻¹ChemAxon
Polarizability32.9 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07bf-9640000000-63dab33ab67c598b8779Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-003r-1930000000-b90a7add9041c09efb5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-005i-1930000000-524395362f2824760185Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004r-1900000000-f5b2dc8eb6cd3b695581Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-5389ad6755b0b9d3f3b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gr-2290000000-2c27a844d317defb5527Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9540000000-8a05a19349a6eb1a0852Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4ddcf8011b3e19977025Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-3b0d542f8a73ec923a94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-4980000000-3be05aa6c152cc4a87a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-f6b1e08de10b5f29753dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-d2de1be3a5b498179198Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q9-9700000000-4feca2b9a2fe44fb0adcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0590000000-e841763a4ecec6c31d60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2940000000-780b7e85e0bd0df044daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3900000000-80359ff0e43a20860a42Spectrum
Toxicity Profile
Route of ExposureRapid absorption following oral administration. Absolute bioavailability is not known, but at least 77% of a single oral dose of sibutramine is absorbed.
Mechanism of ToxicitySibutramine 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.
MetabolismHepatic 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
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of obesity.
Minimum Risk LevelNot Available
Health EffectsUsing 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.
SymptomsSide effects include dry mouth, anorexia, insomnia, constipation and headache.
TreatmentTreatment 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. (6)
Concentrations
Not Available
DrugBank IDDB01105
HMDB IDHMDB0243547
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSibutramine
Chemspider ID5021
ChEBI ID458192
PubChem Compound ID5210
Kegg Compound IDC07247
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Chris Senanayake, “Methods of preparing didesmethylsibutramine and other sibutramine derivatives.” U.S. Patent US20020183554, issued December 05, 2002.

MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.