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
  • vanoxerina
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
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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Vanoxerine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Vanoxerine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Vanoxerine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Vanoxerine.
5-androstenedioneThe metabolism of Vanoxerine can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Vanoxerine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Vanoxerine.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Vanoxerine.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Vanoxerine.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Vanoxerine.
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 / Symptomatic, recurrent 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 November 02, 2018 08:58