Chemistry:Oxypertine

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Oxypertine, sold under the brand name Oxypertine among others, is an antipsychotic medication of the pertine group which was previously used in the treatment of schizophrenia but is no longer marketed.[1] It was also evaluated for the treatment of anxiety.[2]

Pharmacology

Pharmacodynamics

The drug shows high affinity for the serotonin 5-HT2 and dopamine D2 receptors (Ki = 8.6 nM and 30 nM, respectively).[3] It antagonizes the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.[3][4] Like reserpine and tetrabenazine, oxypertine depletes catecholamines, though not serotonin, possibly contributing to its antipsychotic effectiveness.[5]

Chemistry

Chemically, it is a substituted tryptamine and phenylpiperazine derivative.[6] Its chemical structure is similar to other "pertines" including alpertine, milipertine, and solypertine.[7][8]

History

Oxypertine was first described in the scientific literature by 1962.[9]

Society and culture

Names

Oxypertine is the generic name of the drug and its INN, USAN, BAN, DCF, and JAN.[9][10][11][12] It is also known by its former developmental code name WIN-18501.[9][10][11][12] The drug has been sold under brand names including Equipertine, Forit, Integrin, Lanturil, Lotawin, Opertil, and Oxypertine.[9][10][11][12]

See also

  • Pertine

References

  1. Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8. https://books.google.com/books?id=5S_uhYzKWisC&q=oxypertine%20forit&pg=PA5038. 
  2. "[Clinical evaluation of oxypertine in anxiety conditions]" (in es). Neurologia, Neurocirugia, Psiquiatria 17 (3): 171–180. 1976. PMID 12484. 
  3. 3.0 3.1 Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?. Progress in Medicinal Chemistry. 33. 1996. pp. 185–232. doi:10.1016/s0079-6468(08)70306-0. ISBN 978-0-444-82310-6. PMID 8776944. 
  4. "A systematic study of the pharmacological activities of dopamine antagonists". Life Sciences (Elsevier BV) 24 (24): 2201–2216. June 1979. doi:10.1016/0024-3205(79)90096-1. PMID 388130. 
  5. "Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin". Zeitschrift für Zellforschung und Mikroskopische Anatomie 101 (3): 448–462. 1969. doi:10.1007/BF00335580. PMID 5362847. 
  6. "[Oxypertine, peperazine derivative of tryptophan with neuroleptic and dynamogenic properties]" (in fr). Acta Neurologica et Psychiatrica Belgica 68 (2): 116–127. February 1968. PMID 4972600. 
  7. Progress in Medicinal Chemistry. Elsevier Science. 1996. p. 219. ISBN 978-0-08-086281-1. https://books.google.com/books?id=SDaZ4qcemf8C&pg=PA219. Retrieved 30 October 2024. "Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles." 
  8. The Organic Chemistry of Drug Synthesis, Volume 2. Organic Chemistry Series of Drug Synthesis. Wiley. 1980. pp. 341–343. ISBN 978-0-471-04392-8. https://books.google.com/books?id=r-eqWrMoO18C&pg=PA341. Retrieved 30 October 2024. 
  9. 9.0 9.1 9.2 9.3 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. 2014. p. 924. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA924. Retrieved 2 November 2024. 
  10. 10.0 10.1 10.2 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 779. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA779. Retrieved 2 November 2024. 
  11. 11.0 11.1 11.2 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. 2012. p. 212. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA212. Retrieved 2 November 2024. 
  12. 12.0 12.1 12.2 "List of Antipsychotics". https://drugs.com/international/oxypertine.html.