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Vanoxerine

HCID 3455
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Grundinformationen

CAS
67469-69-6
Standard-SMILES
Fc1ccc(C(OCCN2CCN(CCCc3ccccc3)CC2)c2ccc(F)cc2)cc1
InChIKey
NAUWTFJOPJWYOT-UHFFFAOYSA-N
Summenformel
C28H32F2N2O
Durchschnittliche Molmasse
450,6 g/mol
Monoisotopische Masse
450,24827008

Überblick

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+).

Namen und Bezeichner

Bevorzugter Name
Vanoxerine
IUPAC
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
Englischer Name
Vanoxerine
Summenformel
C28H32F2N2O
Molmasse
450.56

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
67469-69-6

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
5,6
Polarare Oberfläche (TPSA)
15,7 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
10
Schwere Atome
33
Formalladung
0
Komplexität
498

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Solubility<5 mM

Physikochemische Eigenschaften

Siedepunkt
542.7 · 542.7±50.0 °C(Predicted)
Dichte
1.135 · 1.135±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
Soluble in DMSO
Aggregatzustand
Powder
pka
7.55 · 7.55±0.10(Predicted)

Chemie und Industrie

Pharmakologische Informationen

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

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 Eintrag

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.

Zugehörige Reaktionen

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PubChem CID
3455
DTXSID
DTXSID8045143
ChEMBL
CHEMBL281594
ChEBI
CHEBI:64089
UNII
90X28IKH43
Nikkaji
J259.982A
Metabolism/Metabolites · 2 Einträge

_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.
Absorption, Distribution and Excretion · 4 Einträge

At doses of 25, 75 or 125 mg, vanoxerine had a corresponding Cmax of 17.9, 81.1 and 236.5 nmol/L and a corresponding AUC of 81, 365 and 1116 h⋅nmol/L when given orally to healthy male volunteers (n=14). In this same set of subjects, tmax was reached at 0.91, 0.93 and 1.13 h at oral doses of 25, 75 or 125 mg, respectively. The oral bioavailability of this drug depends on food intake. Compared with those fasting, the bioavailability of vanoxerine in volunteers taking a low-fat and a high-fat meal was 76% and 255% higher, respectively.

The majority of vanoxerine is excreted in urine, bile and feces.

Vanoxerine is capable of crossing the blood-brain barrier and distributing to several organs such as fat tissue, lungs, liver and the gastrointestinal tract. Vanoxerine has a large volume of distribution.

At 25, 75 and 125 mg/day, vanoxerine had a corresponding oral clearance of 660, 478 and 250 L/h.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Vanoxerine dihydrochloride