Details of the Drug

General Information of Drug (ID: DMBQPA5)

Drug Name
Vanoxerine
Synonyms
Vanoxerina; Vanoxerinum; Vanoxerine [INN]; D-052; Vanoxerina [INN-Spanish]; Vanoxerinum [INN-Latin]; Piperazine, 1-(2-(bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)-, dihydrochloride; 1-(2 (Bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine di-hcl; 1-(2-(Bis(p-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine; 1-(2-bis-[4-FLUOROPHENYL]-METHOXYETHYL)-4-(3-PHENYL-2-PROPYL)PIPERAZINE; 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
Indication
Disease Entry ICD 11 Status REF
Cocaine addiction 6C45.2 Discontinued in Phase 1 [1]
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 450.6
Logarithm of the Partition Coefficient (xlogp) 5.6
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C28H32F2N2O
IUPAC Name
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
Canonical SMILES
C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
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
InChIKey
NAUWTFJOPJWYOT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3455
ChEBI ID
CHEMBL281594
CAS Number
67469-69-6
UNII
90X28IKH43
DrugBank ID
DB03701
TTD ID
D0N2HF
VARIDT ID
DR00939
INTEDE ID
DR1670
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine transporter (DAT) TTVBI8W SC6A3_HUMAN Blocker [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Sodium-dependent dopamine transporter (SLC6A3) OT39XG28 SC6A3_HUMAN Protein Interaction/Cellular Processes [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Cocaine addiction
ICD Disease Classification 6C45.2
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine transporter (DAT) DTT SLC6A3 1.08E-03 -3.08 -1.99
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.76E-01 1.26E-01 8.27E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Emerging pharmacological strategies in the fight against cocaine addiction. Expert Opin Emerg Drugs. 2006 Mar;11(1):91-8.
2 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.
3 Vanoxerine National Institute on Drug Abuse. Curr Opin Investig Drugs. 2000 Oct;1(2):241-51.