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]
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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: CHEBI:64089
CAS Number: 67469-69-6
DrugBank ID: DB03701
TTD ID: D0N2HF
VARIDT ID: DR00939
INTEDE ID: DR1670

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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 2C8 (CYP2C8)	OTHCWT42	CP2C8_HUMAN	Regulation of Drug Effects	[2]
Cytochrome P450 2E1 (CYP2E1)	OTHQ17JG	CP2E1_HUMAN	Regulation of Drug Effects	[2]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Regulation of Drug Effects	[2]
Sodium-dependent dopamine transporter (SLC6A3)	OT39XG28	SC6A3_HUMAN	Protein Interaction/Cellular Processes	[3]
Synaptic vesicular amine transporter (SLC18A2)	OTUOMMM6	VMAT2_HUMAN	Protein Interaction/Cellular Processes	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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.
4	Synaptic vesicular monoamine transporter expression: distribution and pharmacologic profile. Brain Res Mol Brain Res. 1994 Mar;22(1-4):219-26. doi: 10.1016/0169-328x(94)90050-7.