Vanoxerine

HCID 3455CAS 67469-69-6

Basic information

Standard SMILES
Fc1ccc(C(OCCN2CCN(CCCc3ccccc3)CC2)c2ccc(F)cc2)cc1
InChIKey
NAUWTFJOPJWYOT-UHFFFAOYSA-N
Molecular formula
C28H32F2N2O
Average molar mass
450.6 g/mol
Monoisotopic mass
450.24827008

Overview

Vanoxerine is an N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration. It has a role as a dopamine uptake inhibitor. It is an ether, an organofluorine compound, a N-alkylpiperazine and a tertiary amino compound. It is a conjugate base of a vanoxerine(2+).

Names & identifiers

Preferred name
Vanoxerine
IUPAC
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
English name
Vanoxerine
Molecular formula
C28H32F2N2O
Molecular weight
450.56

Names & synonyms

Vanoxerine67469-69-6Gbr 12909VanoxerinaVanoxerinumVanoxeamineGBR-12909GBR129091-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine90X28IKH431-(2-(Bis(p-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine
Show more names
Vanoxerine free base1-(2-(di(4-fluorophenyl)-methoxy)-ethyl)-4-(3-phenylpropyl)piperazinePiperazine, 1-[2-[bis(4-fluorophenyl)Methoxy]ethyl]-4-(3-phenylpropyl)-
DTXSID8045143CHEBI:640891-(2-(bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazineRefChem:193710DTXCID60251431-(2 (bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazineVanoxerine [INN]CHEMBL281594

Database identifiers

CAS
67469-69-6
PubChem CID
3455
DTXSID
DTXSID8045143
ChEMBL
CHEMBL281594
ChEBI
CHEBI:64089
UNII
90X28IKH43
Nikkaji
J259.982A

Properties

Computed structural properties

XLogP
5.6
Topological polar surface area
15.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
10
Heavy atoms
33

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Solubility<5 mM

Physicochemical properties

Boiling point
542.7 · 542.7±50.0 °C(Predicted)
Density
1.135 · 1.135±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
solubility
Soluble in DMSO
form
Powder
pka
7.55 · 7.55±0.10(Predicted)

Chemistry & industry

Pharmacology

Protein BindingThe plasma protein binding of vanoxerine is 99% at 0.1, 0.4 and 1 μM.
Pharmacodynamics · 1 item

Vanoxerine inhibits dopamine reuptake by binding and blocking the dopamine transporter. The use of vanoxerine has been evaluated as a potential substitute of cocaine in the treatment of drug addiction. In primates, the intravenous administration of vanoxerine reduced cocaine self-administration at 1 mg/kg and eliminated it at 3 mg/kg. The stimulant profile of cocaine was not detected in healthy volunteers (n=8) receiving vanoxerine for 2 weeks, suggesting a lack of abuse potential of vanoxerine. However, other studies have found that vanoxerine has at least moderate potential to be abused by humans. The antiarrhythmic potential of vanoxerine has also been assessed. A clinical study evaluating the efficacy of vanoxerine on the conversion of atrial fibrillation (AF) or atrial flutter (AFL) to normal sinus rhythm reported that, within 24 hours, a significant proportion of symptomatic AF/AFL patients treated with 200, 300 and 400 mg of vanoxerine converted to sinus rhythm. In studies that evaluated doses ranging from 25 to 300 mg, vanoxerine was considered to be safe and tolerable.

Mechanism of Action · 1 item

Vanoxerine is a highly selective dopamine transporter antagonist. Due to its ability to inhibit dopamine reuptake, it has been suggested that vanoxerine may be beneficial in treating cocaine addiction. Cocaine increases the amount of dopamine in the synapse by attaching and blocking the dopamine transporter. Compared to cocaine, vanoxerine has a higher affinity for the dopamine transporter and a slower dissociation rate, without the stimulant profile of cocaine. The use of vanoxerine to treat conditions characterized by low levels of dopamine, such as Parkinson's disease and depression, has also been investigated. Vanoxerine is also a potent blocker of the hKV11.1 (hERG) cardiac potassium channel. Even at low concentrations, vanoxerine is capable of blocking calcium and sodium currents without having a significant effect on QT interval, action potential waveforms and transmural dispersion of repolarization. Because of this, the anti-arrhythmic and anti-atrial fibrillatory properties of vanoxerine have been investigated.

Biological Half-LifeThe mean elimination half-life of vanoxerine was 53.5 h at 75 mg/day and 66 h at 125 mg/day.
Metabolism/Metabolites · 2 items

_In vitro_ studies suggest that vanoxerine is mostly metabolized by CYP3A4. CYP2C8 and CYP2E1 may also contribute to the metabolism of this drug. CYP3A4 selective-inhibitors may interact with vanoxerine.

Vanoxerine has known human metabolites that include 1-Phenyl-3-[4-[2-(4,4'-difluorobenzhydryloxy)ethyl]piperazino]-1-propanol and 4-[3-[4-[2-[Bis(4-fluorophenyl)methoxy]ethyl]piperazino]propyl]phenol.

MeSH Pharmacological ClassificationDrugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake.

Applications

UsesVanoxerine (GBR-12909) is a competitive, potent, and highly selective dopamine reuptake inhibitor (Ki=1 nM). Vanoxerine (GBR-12909) binds to the target site on the dopamine transporter (DAT)[1].

Upstream & downstream products

Downstream products

Suppliers10 total

Hangzhou Sage Chemical Co., Ltd.+86057186818502 13588463833 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
斯派螺(武汉)药物研发有限公司[email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Vanoxerine is an N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration. It has a role as a dopamine uptake inhibitor. It is a N-alkylpiperazine, an organofluorine compound, a tertiary amino compound and an ether. It is a conjugate base of a vanoxerine(2+).

Related reactions

8 records

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