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20-September-2008 09:55:56 - Vanoxerine Vanoxerine Systematic IUPAC name 1-2-bis4-fluorophenylmethoxyethyl-4-3-phenylpropylpiperazine Identifiers CAS number 67469-78-7 ATC code ? PubChem 3455 Chemical data Formula C28H33F2N2O Mol. mass 450.563 g/mol freebase; 523.494 g/mol dihydrochloride Pharmacokinetic data Bioavailability ? Metabolism ? Half life 6 hours approx Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Investigational New Medicine Routes ? Vanoxerine, also known as GBR-12909, is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor. GBR-12909 binds to the target site on the dopamine reuptake transporter around 500 times more strongly than cocaine, but has only mild stimulant effects, because as well as inhibiting the reuptake of dopamine, GBR-12909 inhibits dopamine release, and so produces only a slight elevation of dopamine levels.1 Vanoxerine has been researched for use in treating cocaine dependence both as a substitute for cocaine and to block the rewarding effects. This strategy of using a competing agonist with a longer half-life has been successfully used to treat addiction to opiates such as heroin by substituting with methadone. It is hoped that vanoxerine will be of similar use in treating cocaine addiction.23 Research also indicates that vanoxerine may have additional mechanisms of action including antagonist action at nicotinic acetylcholine receptors,4 and it has also been shown to reduce the consumption of alcohol in animal models of alcohol abuse.5 Vanoxerine has been through human trials up to Phase 2, but has not been developed for clinical use, although it is still being researched.678 A decanoate ester of vanoxerine, DBL-583, has also been developed, which slowly breaks down in the body and lasts for up to a month after a single injection.910 DBL-583 DBL-583 References ^ Singh S. Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists. Chemistry Reviews, 2000. 1003: 925-1024. ^ Vetulani J. Drug addiction. Part III. Pharmacotherapy of addiction. Polish Journal of Pharmacology. 2001 Sep-Oct;535:415-34. ^ Preti A. New developments in the pharmacotherapy of cocaine abuse. Addiction Biology. 2007 Jun;122:133-51. ^ Szasz BK, Vizi ES, Kiss JP. Nicotinic acetylcholine receptor antagonistic property of the selective dopamine uptake inhibitor, GBR-12909 in rat hippocampal slices. Neuroscience. 2007 Mar 2;1451:344-9. ^ Kamdar NK, Miller SA, Syed YM, Bhayana R, Gupta T, Rhodes JS. Acute effects of naltrexone and GBR 12909 on ethanol drinking-in-the-dark in C57BL/6J mice. Psychopharmacology Berlin. 2007 Jun;1922:207-17. ^ Søgaard U, Michalow J, Butler B, et al 1990. A tolerance study of single and multiple dosing of the selective dopamine uptake inhibitor GBR 12909 in healthy subjects. International clinical psychopharmacology 5 4: 237-51. PMID 2150527. ^ Preti A. Vanoxerine National Institute on Drug Abuse. Current Opinion in Investigational Drugs. 2000 Oct;12:241-51. ^ Gorelick DA, Gardner EL, Xi ZX. Agents in development for the management of cocaine abuse. Drugs. 2004;6414:1547-73. ^ Baumann MH, Ayestas MA, Sharpe LG, Lewis DB, Rice KC, Rothman RB. Persistent antagonism of methamphetamine-induced dopamine release in rats pretreated with GBR12909 decanoate. Journal of Pharmacology and Experimental Therapeutics. 2002 Jun;3013:1190-7. ^ Baumann MH, Phillips JM, Ayestas MA, Ali SF, Rice KC, Rothman RB. Preclinical evaluation of GBR12909 decanoate as a long-acting medication for methamphetamine dependence. Annals of the New York Academy of Sciences. 2002 Jun;965:92-108. v d e Stimulants Alkylamines Cyclopentamine Geranamine Isometheptene Octodrine Propylhexedrine Tuamine Alphapyrrolidinylalkiophenones α-PPP MDPPP MDPV MPBP MPHP MPPP MOPPP Pyrovalerone Cholinergics ABT-089 ABT-418 Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine Rivanicline Tebanicline Varenicline Convulsants Bicuculline DMCM Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil Carphedon Modafinil Phenethylamines 4-Bromomethcathinone 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone 4-Methylmethcathinone 4-MTA Aletamine Amfepentorex Amphechloral Amphetamine Dextroamphetamine, Adderall Amphetaminil Benzphetamine Bupropion Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Diethylpropion Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Ephedrine Epinephrine Ethcathinone Ethylamphetamine Fenethylline Fenfluramine Fenproporex Fludorex Furfenorex Levomethamphetamine Lisdexamfetamine MDMA Mefenorex Methamphetamine Methcathinone Methoxyphedrine Methylone Octopamine Ortetamine Parahydroxyamphetamine PCA PIA PMA PMEA PMMA PPAP Phendimetrazine Phenmetrazine Phentermine Phenylephrine Phenylpropanolamine Propylamphetamine Pseudoephedrine Selegiline Synephrine Tiflorex Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex Aminorex Clominorex Fenozolone Fluminorex Pemoline Thozalinone Piperazines 2C-B-BZP BZP GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine Piperidines 2-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate HDMP-28 --Methyl-1-methyl-4β-2-naphthylpiperidine-3β-carboxylate Methylphenidate Dexmethylphenidate Nocaine Phacetoperane Pipradrol Tropanes 3α-Bis-4-fluorophenylmethoxytropane 3α-4-Chlorophenylphenylmethoxytropane 3-Pseudotropyl-4-fluorobenzoate Altropane IACFT Brasofensine CFT WIN 35,428 β-CIT RTI-55 Cocaethylene Cocaine β-CPPIT Dichloropane RTI-111 Difluoropine FE-β-CPPIT FP-β-CPPIT PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 IPCIT RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 Tesofensine Troparil β-CPT, WIN 35,065-2 WF-23 WF-33 WF-60 Xanthines Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline Others Amineptine Bemegride Benzydamine BPAP Bromantane BTQ Clofenciclan Cypenamine Cyprodenate Diclofensine Dimethocaine Diphenyl prolinol Ethamivan Fencamfamine Feprosidnine Gilutensin GYKI-52895 Hexacyclonate Indanorex Indatraline LR-5182 Mazindol Mesocarb Naphthylisopropylamine Nikethamide Nomifensine Phthalimidopropiophenone Prolintane Sibutramine Yohimbine Zylofuramine See also Sympathomimetic amines Retrieved from http://en..org/wiki/Vanoxerine Categories: Dopamine reuptake inhibitors | Piperazines Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch This page was last modified on 28 May 2008, at 20:06
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