Synthesis of Tetrabenazine and Its Derivatives, Pursuing Efficiency and Selectivity

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Seung-Mann Paek

Abstract

Tetrabenazine is a US Food and Drug Administration (FDA)-approved drug that exhibits a dopamine depleting effect and is used for the treatment of chorea in Huntington's disease. Mechanistically, tetrabenazine binds and inhibits vesicular monoamine transporter type 2, which is responsible for importing neurotransmitters from the cytosol to the vesicles in neuronal cells. This transportation contributes to the release of neurotransmitters inside the cell to the synaptic cleft, resulting in dopaminergic signal transmission. The highly potent inhibitory activity of tetrabenazine has led to its advanced applications and in-depth investigation of prodrug design and metabolite drug discovery. In addition, the synthesis of enantiomerically pure tetrabenazine has been pursued. After a series of research studies, tetrabenazine derivatives such as valbenazine and deutetrabenazine have been approved by the US FDA. In addition, radioisotopically labeled tetrabenazine permits the early diagnosis of Parkinson's disease, which is difficult to treat during the later stages of this disease. These applications were made possible by the synthetic efforts aimed toward the efficient and asymmetric synthesis of tetrabenazine. In this review, various ...Continue Reading

References

May 1, 1966·Biochemical Pharmacology·D E SchwartzA Brossi
Apr 1, 1993·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·J N DaSilvaT J Mangner
Feb 1, 1997·Nuclear Medicine and Biology·D M JewettL C Lee
Sep 15, 2004·Angewandte Chemie·Pablo Espinet, Antonio M Echavarren
Nov 5, 2005·The Journal of Organic Chemistry·Michael E LimmertJohn F Hartwig
Feb 10, 2006·Expert Review of Neurotherapeutics·Christopher Kenney, Joseph Jankovic
Oct 26, 2006·Journal of the American Chemical Society·Naoki SasamotoMikiko Sodeoka
Aug 8, 2007·Archives of Pharmacal Research·Jin-Kyung InJae-Kyung Jung
Mar 19, 2009·Angewandte Chemie·Noah Z BurnsReinhard W Hoffmann
Apr 21, 2009·The Journal of Organic Chemistry·Michael J RishelBruce F Johnson
Mar 18, 2010·Chemistry : a European Journal·Seung-Mann PaekYoung-Ger Suh
Aug 10, 2010·ACS Medicinal Chemistry Letters·Qian-Sheng YuNigel H Greig
Aug 11, 2010·Drug News & Perspectives·Liming Shao, Michael C Hewitt
Sep 28, 2010·The American Journal of Geriatric Pharmacotherapy·David R P Guay
Oct 22, 2011·Expert Review of Neurotherapeutics·Joseph Jankovic, Kathleen Clarence-Smith
Mar 17, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Seung-Mann Paek
Jun 20, 2012·Angewandte Chemie·Jun Xuan, Wen-Jing Xiao
Jun 30, 2012·Organic Letters·Manuel Johannes, Karl-Heinz Altmann
Jul 1, 2014·Proceedings of the National Academy of Sciences of the United States of America·Kelly M LohrGary W Miller
Nov 7, 2015·The Journal of Organic Chemistry·Lindsey R OrgrenChristopher Carl Marvin
Oct 11, 2016·Annals of Neurosciences·Navneet KaurVinod Gauttam
Apr 14, 2017·The Journal of Pharmacology and Experimental Therapeutics·Dimitri E GrigoriadisHaig Bozigian
Nov 17, 2017·Nature Reviews. Neuroscience·Nora D VolkowRuben Baler
Mar 3, 2018·Drug Design, Development and Therapy·Marissa Dean, Victor W Sung
Feb 1, 2019·Neurodegenerative Disease Management·Nicki Niemann, Joohi Jimenez-Shahed
Jun 18, 2019·Therapeutic Advances in Psychopharmacology·Rikinkumar S PatelMuhammad Khalid Zafar
Jan 1, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bo Reum SongSeung-Mann Paek

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Citations

Jun 24, 2021·Medicine·Qiaoqi Li, Hong Zhu
Jul 3, 2021·The Journal of Organic Chemistry·Yusuke SatoJason E Hein

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Methods Mentioned

BETA
acetylation
X-ray
amidation
γ-ray

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