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Sibutramine

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Also known as ButraminCf-alliMedariaRacemic sibutramineReductilSibutraminaSID49732001SID174007250C0164878

Summary

Sibutramine (CHEMBL1419) is an approved small molecule (ATC A08AA10) targeting CYP2B6, KCND3, and SLC6A2; indicated across 1 condition including obesity disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: A08AA10
  • Targets: 5 (CYP2B6, KCND3, SLC6A2…)
  • Indications: 1 condition
  • Clinical trials: 28
  • Chemistry: 279.8 Da · C17H26ClN

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1419
NameSibutramine
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID5210
ATCA08AA10
Molecular formulaC17H26ClN
Molecular weight279.8
InChIKeyUNAANXDKBXWMLN-UHFFFAOYSA-N

SMILES: CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N(C)C

IUPAC name: 1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine

Also known as: Butramin, Cf-alli, Medaria, Racemic sibutramine, Reductil, Sibutramina, Sibutramine, SID49732001, sibutramine, SID174007250, SIBUTRAMINE, C0164878

Parent form; salt/anhydrous children: CHEMBL1200765, CHEMBL3989830

Patent coverage: 7,806 distinct patent families (30,503 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CYP2B6CYP2B6Inhibition5.790.1%P20813
KCND3Kv4.34.75.5%Q9UK17
SLC6A2NETInhibition5.250.4%P23975
SLC6A3DATInhibition6.30.2%Q01959
SLC6A4SERTInhibition5.960.7%P31645

Broader ChEMBL bioactivity targets: 11 (assay-derived). Sample: 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Muscarinic acetylcholine receptor M2, Sodium-dependent noradrenaline transporter, 5-hydroxytryptamine receptor 2A, Sodium-dependent serotonin transporter, Kappa-type opioid receptor, Sodium-dependent dopamine transporter.

Bioactivity

ChEMBL activities: 18 potent at pChembl ≥ 5 of 21 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
SLC6A26.44AC50360nMCHEMBL_ACT_25144971
SLC6A36.3Ki502nMCHEMBL_ACT_7813777
SLC6A36.2IC50632nMCHEMBL_ACT_7813776
SLC6A36.12AC50750nMCHEMBL_ACT_25123921
ADRA2C6.12AC50758.5nMCHEMBL_ACT_25148599
HTR2A5.99AC501020nMCHEMBL_ACT_25173605
ADRA2B5.96Ki1091nMCHEMBL_ACT_7811695
SLC6A45.96Ki1108nMCHEMBL_ACT_7815936
SLC6A45.92AC501200nMCHEMBL_ACT_25150306
SLC6A45.68IC502085nMCHEMBL_ACT_7815935
ADRA2A5.67AC502138nMCHEMBL_ACT_25156124
ADRA2B5.62IC502390nMCHEMBL_ACT_7811694
ADRA2C5.42AC503800nMCHEMBL_ACT_25147847
ADRA2B5.37AC504300nMCHEMBL_ACT_25143671
OPRK15.32AC504825nMCHEMBL_ACT_25129398
SLC6A25.25IC505665nMCHEMBL_ACT_7811704
SLC6A25.25Ki5619nMCHEMBL_ACT_7811705
KCNH25.08AC508341nMCHEMBL_ACT_25117823

Target pathways

Aggregated over 5 target gene(s): CYP2B6, KCND3, SLC6A2, SLC6A3, SLC6A4.

Top Reactome pathways

24 total, by targets touching each:

PathwayTargetsGenes
Neuronal System3KCND3, SLC6A3, SLC6A4
SLC-mediated transport of neurotransmitters3SLC6A2, SLC6A3, SLC6A4
Neurotransmitter clearance2SLC6A3, SLC6A4
Transmission across Chemical Synapses2SLC6A3, SLC6A4
Disease2SLC6A2, SLC6A3
Transport of small molecules2SLC6A2, SLC6A3
R-HSA-4253662SLC6A2, SLC6A3
SLC-mediated transmembrane transport2SLC6A2, SLC6A3
SLC transporter disorders2SLC6A2, SLC6A3
Disorders of transmembrane transporters2SLC6A2, SLC6A3
Potassium Channels1KCND3
Voltage gated Potassium channels1KCND3
Fatty acids1CYP2B6
Phase I - Functionalization of compounds1CYP2B6
Xenobiotics1CYP2B6
CYP2E1 reactions1CYP2B6
Dopamine clearance from the synaptic cleft1SLC6A3
Serotonin clearance from the synaptic cleft1SLC6A4
Muscle contraction1KCND3
Cardiac conduction1KCND3
Phase 1 - inactivation of fast Na+ channels1KCND3
Defective neurotransmitter clearance by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)1SLC6A3
Defective SLC6A2 causes orthostatic intolerance (OI)1SLC6A2
Defective transport of neurotransmitters by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)1SLC6A3

Dominant GO biological processes

GO termTargets
transmembrane transport4
neurotransmitter transport3
amino acid transport3
response to xenobiotic stimulus3
obsolete monoamine transport3
sodium ion transmembrane transport3
chemical synaptic transmission2
dopamine uptake involved in synaptic transmission2
norepinephrine uptake2
neurotransmitter reuptake2
xenobiotic metabolic process1
steroid metabolic process1
epoxygenase P450 pathway1
xenobiotic catabolic process1
ketone metabolic process1

Indications & clinical

Indications

1 indication (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
obesity disorder4MONDO:0011122EFO:0001073

Clinical trials

Total trials: 28.

Phase distribution

PhaseTrials
PHASE49
PHASE36
Not specified6
PHASE24
PHASE12
PHASE2/PHASE31

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00044187PHASE4COMPLETEDThe Assessment of a Weight-Gain Agent for the Treatment of Olanzapine-Associated Anti-Obesity Agent in Patients With Schizophrenia, Schizophreniform Disorder, Schizoaffective Disorder, and Bipolar I Disorder
NCT00115063PHASE4TERMINATEDLOSS- Louisiana Obese Subjects Study
NCT00433641PHASE4COMPLETEDWeight Loss in Response to Sibutramine (MERIDIA) is Influenced by the Inherited Genes
NCT00463112PHASE4COMPLETEDEffect of Diet Plus Sibutramine on Hormonal and Metabolic Features in Overweight and Obese Women With PCOS
NCT00537810PHASE4COMPLETEDTreatment of Binge Eating in Obese Patients in Primary Care
NCT00729963PHASE4COMPLETEDSibutramine Versus Continuous Positive Airway Pressure (CPAP)in Obstructive Sleep Apnea (OSA) Patients
NCT01170364PHASE4TERMINATEDStudying the Effects of Sibutramine on Eating Behavior
NCT01475019PHASE4UNKNOWNThe Effect of Weight Loss on Anti-Müllerian Hormone Levels in Women With Polycystic Ovary Syndrome (PCOS)
NCT05821543PHASE4COMPLETEDEfficacy and Safety of Sibutramin-containing Drugs in Patient With Alimentary Obesity
NCT00134199PHASE2/PHASE3COMPLETEDA Study Of 6-Month Duration To Evaluate The Weight Loss Effect Of Various Doses Of CP-945,598 In Obese Subjects
NCT00261911PHASE3COMPLETEDA Study of Sibutramine in Overweight Adolescents to Assess Weight Loss and Safety.
NCT00402584PHASE3COMPLETEDA Study to Examine the Efficacy and Safety of Meridia® (Sibutramine Hydrochloride) in Binge-Eating Disorder
NCT00677391PHASE3COMPLETEDEfficacy and Safety Study of Sibutramine in Overweight Non-Diabetic Malaysian Population
NCT00679653PHASE3COMPLETEDBlood Pressure and Weight Trajectory on a Dual Antihypertensive Combination Plus Sibutramine Versus Placebo in Obese Hypertensives
NCT00941382PHASE3UNKNOWNSibutramine-metformin Combination Versus Sibutramine and Metformin Monotherapy in Obese Patients
NCT01047657PHASE3COMPLETEDEffects of Weight Loss in Obese Difficult-to-treat Asthmatics
NCT00330525PHASE2COMPLETEDPharmacodynamic Effects of Sibutramine on Gastric Function in Obesity
NCT00402077PHASE2COMPLETEDA Study to Examine the Safety, Tolerability, and Body Weight Effect of Pramlintide Alone and in Combination With Oral Antiobesity Agents in Overweight and Obese Subjects
NCT00537420PHASE2COMPLETEDA Study of Nasal PYY3-36 and Placebo for Weight Loss in Obese Subjects
NCT00993421PHASE2TERMINATEDA Weight Loss Study in Overweight Men and Women
NCT00914212PHASE1COMPLETEDA Functional Magnetic Resonance Imaging (fMRI) Study in Overweight and Obese Men (0000-103)
NCT01597609PHASE1COMPLETEDA Study to Characterise the Physiology of Weight Loss and Regain Under Dietary, Behavioural and Pharmacological Interventions in Healthy Obese Subjects
NCT07588750Not specifiedNOT_YET_RECRUITINGRetrospective Evaluation of Sibutramine-Topiramate Therapy for Obesity in Real-World Outpatient Practice
NCT00037752Not specifiedCOMPLETEDSibutramine to Reduce Weight Gain and Improve Smoking Cessation Rates
NCT00212173Not specifiedCOMPLETEDAdolescent Weight Management Study
NCT00829283Not specifiedCOMPLETEDTreatment of Obesity and Binge Eating: Behavioral Weight Loss Versus Stepped Care
NCT01023139Not specifiedUNKNOWNEfficacy in Adolescents of Continued Behavior Modification Following a Six Month Sibutramine-based Weight Management Intervention
NCT01184560Not specifiedCOMPLETEDAssess the Additional Weight Loss Effect of Orlistat Used in Combination With Sibutramine

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

707 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DesvenlafaxineChEMBL + PubChemPhase 4 (approved)KCND3, SLC6A2, SLC6A3, SLC6A4
DULOXETINEChEMBL + PubChemPhase 4 (approved)KCND3, SLC6A2, SLC6A3, SLC6A4
NEBIVOLOLChEMBL + PubChemPhase 4 (approved)KCND3, SLC6A2, SLC6A3, SLC6A4
PimozideChEMBL + PubChemPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3, SLC6A4
PropafenoneChEMBL + PubChemPhase 4 (approved)KCND3, SLC6A2, SLC6A3, SLC6A4
RIFAMPINChEMBL + PubChemPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3, SLC6A4
SUNITINIBChEMBL + PubChemPhase 4 (approved)KCND3, SLC6A2, SLC6A3, SLC6A4
TadalafilChEMBL + PubChemPhase 4 (approved)KCND3, SLC6A2, SLC6A3, SLC6A4
VorapaxarChEMBL + PubChemPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3, SLC6A4
ETHINYL ESTRADIOLChEMBLPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3, SLC6A4
SERTRALINEChEMBLPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3, SLC6A4
TAMOXIFENChEMBLPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3, SLC6A4
THIOTEPAChEMBLPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3, SLC6A4
PHENCYCLIDINEChEMBLPhase 2CYP2B6, SLC6A2, SLC6A3, SLC6A4
saxagliptinPubChemApprovedCYP2B6, SLC6A2, SLC6A3, SLC6A4
AfatinibChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AMITRIPTYLINEChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ClozapineChEMBL + PubChemPhase 4 (approved)CYP2B6, SLC6A2, SLC6A4
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
IdelalisibChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
NelfinavirChEMBL + PubChemPhase 4 (approved)KCND3, SLC6A2, SLC6A3
OlodaterolChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
PIMAVANSERINChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
REGORAFENIBChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
TAFENOQUINEChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
UMECLIDINIUMChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ACETOPHENAZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AMIODARONEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AMOXAPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ARIPIPRAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ASENAPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ASTEMIZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ATOMOXETINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AZELASTINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BAZEDOXIFENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENFLUOREXChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENZPHETAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENZTROPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENZYDAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BEPRIDILChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BOSUTINIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BREXPIPRAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMHEXINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMODIPHENHYDRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMPERIDOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BUPROPIONChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CABERGOLINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CALCITRIOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CANNABIDIOLChEMBLPhase 4 (approved)CYP2B6, SLC6A2, SLC6A3
CARBINOXAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CARVEDILOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CELECOXIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CETIRIZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORHEXIDINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPHENTERMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPROMAZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPROTHIXENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 29

This page pulls from 29 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot