IUPAC_name = 1- [2- [bis(4-fluorophenyl)methoxy] ethyl] -4-(3-phenylpropyl)piperazine

width = 250
CAS_number= 67469-78-7
C=28 | H=33 | F=2 | N=2 | O=1
molecular_weight = 450.563 g/mol (freebase); 523.494 g/mol (dihydrochloride)
metabolism =
elimination_half-life= 6 hours approx
excretion =
pregnancy_category =
legal_status = Investigational New Medicine

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. [Singh S. Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists. "Chemistry Reviews", 2000. 100(3): 925-1024.]

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. [Vetulani J. Drug addiction. Part III. Pharmacotherapy of addiction. "Polish Journal of Pharmacology". 2001 Sep-Oct;53(5):415-34.] [Preti A. New developments in the pharmacotherapy of cocaine abuse. "Addiction Biology". 2007 Jun;12(2):133-51.]

Research also indicates that vanoxerine may have additional mechanisms of action including antagonist action at nicotinic acetylcholine receptors, [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;145(1):344-9.] and it has also been shown to reduce the consumption of alcohol in animal models of alcohol abuse. [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;192(2):207-17.]

Vanoxerine has been through human trials up to Phase 2, but has not been developed for clinical use, although it is still being researched. [cite journal |author=Søgaard U, Michalow J, Butler B, "et al" |title=A tolerance study of single and multiple dosing of the selective dopamine uptake inhibitor GBR 12909 in healthy subjects |journal=International clinical psychopharmacology |volume=5 |issue=4 |pages=237–51 |year=1990 |pmid=2150527 |doi=] [Preti A. Vanoxerine National Institute on Drug Abuse. "Current Opinion in Investigational Drugs". 2000 Oct;1(2):241-51.] [Gorelick DA, Gardner EL, Xi ZX. Agents in development for the management of cocaine abuse. "Drugs". 2004;64(14):1547-73.]

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. [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;301(3):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.]


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