Identification

Name
Vanoxerine
Accession Number
DB03701  (EXPT03312)
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • 1-(2-(bis(p-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine
External IDs
GBR 12909 / GBR-12909
Product Ingredients
IngredientUNIICASInChI Key
Vanoxerine hydrochlorideMWO1IP03EV67469-78-7MIBSKSYCRFWIRU-UHFFFAOYSA-N
Categories
UNII
90X28IKH43
CAS number
67469-69-6
Weight
Average: 450.574
Monoisotopic: 450.248269984
Chemical Formula
C28H32F2N2O
InChI Key
NAUWTFJOPJWYOT-UHFFFAOYSA-N
InChI
InChI=1S/C28H32F2N2O/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23/h1-3,5-6,8-15,28H,4,7,16-22H2
IUPAC Name
1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine
SMILES
FC1=CC=C(C=C1)C(OCCN1CCN(CCCC2=CC=CC=C2)CC1)C1=CC=C(F)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USodium-dependent dopamine transporterNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AmiodaroneThe metabolism of Vanoxerine can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Vanoxerine can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Vanoxerine can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Vanoxerine can be decreased when combined with Atomoxetine.Approved
BoceprevirThe metabolism of Vanoxerine can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Vanoxerine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Vanoxerine can be decreased when it is combined with Bosentan.Approved, Investigational
CarbamazepineThe metabolism of Vanoxerine can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Vanoxerine can be increased when it is combined with Ceritinib.Approved
ClarithromycinThe metabolism of Vanoxerine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Vanoxerine can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Vanoxerine can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Vanoxerine can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Vanoxerine can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Vanoxerine can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Vanoxerine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Vanoxerine can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Vanoxerine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Vanoxerine can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Vanoxerine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Vanoxerine can be decreased when combined with Delavirdine.Approved
DihydroergotamineThe metabolism of Vanoxerine can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Vanoxerine can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Vanoxerine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Vanoxerine can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Vanoxerine can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Vanoxerine can be decreased when combined with Erythromycin.Approved, Vet Approved
FluconazoleThe metabolism of Vanoxerine can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Vanoxerine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Vanoxerine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Vanoxerine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Vanoxerine can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Vanoxerine can be increased when it is combined with Fusidic Acid.Approved
ImatinibThe metabolism of Vanoxerine can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Vanoxerine can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Vanoxerine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Vanoxerine can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Vanoxerine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Vanoxerine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Vanoxerine can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Vanoxerine can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Vanoxerine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Vanoxerine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Vanoxerine can be increased when combined with Lumacaftor.Approved
MifepristoneThe serum concentration of Vanoxerine can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Vanoxerine can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Vanoxerine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Vanoxerine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Vanoxerine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Vanoxerine can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Vanoxerine can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Vanoxerine can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Vanoxerine can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Vanoxerine can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Vanoxerine can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Vanoxerine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Vanoxerine can be increased when combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Vanoxerine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Vanoxerine can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Vanoxerine can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Vanoxerine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Vanoxerine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Vanoxerine can be increased when combined with Rifapentine.Approved
SaquinavirThe metabolism of Vanoxerine can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Vanoxerine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Vanoxerine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Vanoxerine can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Vanoxerine can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Vanoxerine can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Vanoxerine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Vanoxerine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Vanoxerine can be decreased when combined with Telithromycin.Approved
TiclopidineThe metabolism of Vanoxerine can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Vanoxerine can be decreased when it is combined with Tocilizumab.Approved
VenlafaxineThe metabolism of Vanoxerine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Vanoxerine can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Vanoxerine can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Vanoxerine can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3455
PubChem Substance
46504818
ChemSpider
3337
BindingDB
22165
ChEBI
64089
ChEMBL
CHEMBL281594
Therapeutic Targets Database
DCL001032
Wikipedia
Vanoxerine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentCocaine Abuse / Cocaine-Related Disorders1
1Unknown StatusTreatmentCocaine-Related Disorders3
2CompletedTreatmentAtrial Flutter / Recurrent Symptomatic Atrial Fibrillation1
3TerminatedTreatmentAtrial Fibrillation or Flutter1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00139 mg/mLALOGPS
logP4.9ALOGPS
logP6.24ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)8.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.71 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity130.38 m3·mol-1ChemAxon
Polarizability49.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8735
Blood Brain Barrier+0.8614
Caco-2 permeable+0.5075
P-glycoprotein substrateNon-substrate0.7857
P-glycoprotein inhibitor INon-inhibitor0.7627
P-glycoprotein inhibitor IINon-inhibitor0.9403
Renal organic cation transporterNon-inhibitor0.6987
CYP450 2C9 substrateNon-substrate0.7336
CYP450 2D6 substrateNon-substrate0.8289
CYP450 3A4 substrateSubstrate0.5078
CYP450 1A2 substrateInhibitor0.8849
CYP450 2C9 inhibitorNon-inhibitor0.5778
CYP450 2D6 inhibitorNon-inhibitor0.8997
CYP450 2C19 inhibitorInhibitor0.6866
CYP450 3A4 inhibitorInhibitor0.5496
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6695
Ames testAMES toxic0.7917
CarcinogenicityCarcinogens 0.5931
BiodegradationNot ready biodegradable0.9967
Rat acute toxicity2.7191 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.643
hERG inhibition (predictor II)Non-inhibitor0.8415
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Phenylpropylamines / Benzylethers / N-alkylpiperazines / Fluorobenzenes / Aralkylamines / Aryl fluorides / Trialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
Diphenylmethane / Phenylpropylamine / Benzylether / Fluorobenzene / Halobenzene / Aralkylamine / N-alkylpiperazine / Aryl fluoride / Aryl halide / 1,4-diazinane
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, tertiary amino compound, ether, N-alkylpiperazine (CHEBI:64089)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Preti A: Vanoxerine National Institute on Drug Abuse. Curr Opin Investig Drugs. 2000 Oct;1(2):241-51. [PubMed:11249581]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Cherstniakova SA, Bi D, Fuller DR, Mojsiak JZ, Collins JM, Cantilena LR: Metabolism of vanoxerine, 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine, by human cytochrome P450 enzymes. Drug Metab Dispos. 2001 Sep;29(9):1216-20. [PubMed:11502731]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 17:28