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CHEBI:64089 - vanoxerine

Default Structure
ChEBI IDCHEBI:64089
ChEBI Namevanoxerine
Stars
DefinitionAn 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.
Last Modified25 February 2016
SubmitterSteve
DownloadsMolfile
FormulaC28H32F2N2O
Net Charge0
Average Mass450.573
Monoisotopic Mass450.24827
SMILESFc1ccc(C(OCCN2CCN(CCCc3ccccc3)CC2)c2ccc(F)cc2)cc1
InChIInChI=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
InChIKeyNAUWTFJOPJWYOT-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
dopamine uptake inhibitor  A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
Applications:
dopamine uptake inhibitor  A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
anti-arrhythmia drug  A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
ChEBI Ontology
Outgoing Relation(s)
vanoxerine (CHEBI:64089) has role anti-arrhythmia drug (CHEBI:38070)
vanoxerine (CHEBI:64089) has role dopamine uptake inhibitor (CHEBI:51039)
vanoxerine (CHEBI:64089) is a N-alkylpiperazine (CHEBI:46845)
vanoxerine (CHEBI:64089) is a ether (CHEBI:25698)
vanoxerine (CHEBI:64089) is a organofluorine compound (CHEBI:37143)
vanoxerine (CHEBI:64089) is a tertiary amino compound (CHEBI:50996)
vanoxerine (CHEBI:64089) is conjugate base of vanoxerine(2+) (CHEBI:64087)
Incoming Relation(s)
vanoxerine(2+) (CHEBI:64087) is conjugate acid of vanoxerine (CHEBI:64089)
IUPAC Name 
1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine
INNs  Source
vanoxerinaChemIDplus
vanoxerineChemIDplus
vanoxerinumChemIDplus
Synonyms  Source
GBR 12909ChEBI
GBR-12909ChEMBL
GBR12909ChEBI
Manual XrefsDatabases
LSM-2703LINCS
VanoxerineWikipedia
Registry NumbersSources
Reaxys:587912Reaxys
CAS:67469-69-6ChemIDplus
Citations