Citizendia

Vanoxerine
Systematic (IUPAC) name
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
Identifiers
CAS number67469-78-7
ATC code ?
PubChem3455
Chemical data
FormulaC28H33F2N2O 
Mol. mass450. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Fluorine, fluorum meaning "to flow" is the Chemical element with the symbol F and Atomic number 9 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 563 g/mol (freebase); 523. 494 g/mol (dihydrochloride)
Pharmacokinetic data
Bioavailability ?
Metabolism ?
Half life6 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. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction In Pharmacology and Toxicology, a route Piperazine is an Organic compound that consists of a six-membered ring containing two opposing nitrogen atoms Dopamine Reuptake Inhibitors ( DARI) Dopamine Uptake Inhibitors, Dopamine Transporter Inhibitors are compounds that inhibit the Reuptake of extracellular 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. Dopamine is a Hormone and Neurotransmitter occurring in a wide variety of animals including both vertebrates and invertebrates Reuptake, or re-uptake, is the reabsorption of a Neurotransmitter by the Neurotransmitter transporter of a pre-synaptic Neuron after Cocaine ( benzoylmethyl ecgonine) is a Crystalline Tropane Alkaloid that is obtained from the leaves of the Coca plant [1]

Vanoxerine has been researched for use in treating cocaine dependence both as a substitute for cocaine and to block the rewarding effects. Cocaine dependence (or addiction) is physical and psychological dependency on the regular use of Cocaine. 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. An agonist is a term used to describe a type of ligand or drug that binds and alters the activity of a receptor. Heroin ( INN: diacetylmorphine, BAN: diamorphine) is a semi-synthetic opioid synthesized from Morphine, a derivative Methadone ( Dolophine Amidone Methadose Physeptone Heptadon and many others is a synthetic Opioid, used medically as an Analgesic, Antitussive It is hoped that vanoxerine will be of similar use in treating cocaine addiction. [2][3]

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. Structure Nicotinic receptors with a molecular mass of 290 kDa, are made up of five subunits arranged symmetrically around the central pore. [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. [6][7][8]

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. Decanoic acid is a type of Carboxylic acid.Its formula is CH3(CH28COOH Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least [9][10]

DBL-583
DBL-583

References

  1. ^ Singh S. Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists. Chemistry Reviews, 2000. 100(3): 925-1024.
  2. ^ Vetulani J. Drug addiction. Part III. Pharmacotherapy of addiction. Polish Journal of Pharmacology. 2001 Sep-Oct;53(5):415-34.
  3. ^ Preti A. New developments in the pharmacotherapy of cocaine abuse. Addiction Biology. 2007 Jun;12(2):133-51.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.  
  7. ^ Preti A. Vanoxerine National Institute on Drug Abuse. Current Opinion in Investigational Drugs. 2000 Oct;1(2):241-51.
  8. ^ Gorelick DA, Gardner EL, Xi ZX. Agents in development for the management of cocaine abuse. Drugs. 2004;64(14):1547-73.
  9. ^ 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.
  10. ^ 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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