Chemistry:Seproxetine
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| Elimination half-life | 4–16 days |
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| Formula | C16H16F3NO |
| Molar mass | 295.305 g·mol−1 |
Seproxetine, also known as (S)-norfluoxetine, is a selective serotonin reuptake inhibitor (SSRI).[1][2] It is the S enantiomer of norfluoxetine, the main active metabolite of the widely used antidepressant fluoxetine;[3] it is nearly 4 times more selective for stimulating neurosteroid synthesis relative to serotonin reuptake inhibition than fluoxetine.[4] It is formed through the demethylation, or removal of a methyl group, of norfluoxetine.[5] Seproxetine is both an inhibitor of serotonin and dopamine transporters, 5-HT2A and 5-HT2C receptors.[6] It was being investigated by Eli Lilly and Company as an antidepressant; however, it inhibited the KvLQT1 protein, which is responsible for the management of the QT interval. This is the time it takes for the heart to contract and recover. Due to the inhibition, the QT interval was prolonged, which could lead to significant cardiac side complications.[7] Due to this, development of the medication was discontinued.[1] Tests on its efficacy found that it was equivalent to fluoxetine, but sixteen times more powerful than the R enantiomer of norfluoxetine.[8]
References
- ↑ 1.0 1.1 "Seproxetine" (in en). DrugBank. University of Alberta. http://www.drugbank.ca/drugs/DB06731.
- ↑ "Drug Interaction of Fluvoxamine and Fluoxetine with Nevirapine in HIV-1-Infected Individuals". Clinical Drug Investigation 23 (10): 629–637. 2003-10-01. doi:10.2165/00044011-200323100-00002. PMID 17535078.
- ↑ "Guidelines for choice of selective serotonin reuptake inhibitor in depressive illness" (in en). Advances in Psychiatric Treatment 7 (3): 170–180. 2001. doi:10.1192/apt.7.3.170. ISSN 1355-5146.
- ↑ "SSRIs act as selective brain steroidogenic stimulants (SBSSs) at low doses that are inactive on 5-HT reuptake". Current Opinion in Pharmacology 9 (1): 24–30. February 2009. doi:10.1016/j.coph.2008.12.006. PMID 19157982.
- ↑ Alvén Fimmerstad T (2022). Could fluorinated pharmaceuticals have an impact on the EOF amount in human blood? (degree of Bachelor thesis). Örebro University.
- ↑ "Solution, and solid investigations on the charge–transfer complexation between seproxetine as a selective serotonin reuptake inhibitor drug with six kinds of π–electron acceptors". Journal of Molecular Liquids 332: 115831. 2021-06-15. doi:10.1016/j.molliq.2021.115831. ISSN 0167-7322. https://www.sciencedirect.com/science/article/pii/S0167732221005560.
- ↑ "Seproxetine". National Center for Advancing Translational Sciences (NCATS). https://drugs.ncats.io/substance/25CO3X0R31.
- ↑ "An efficient synthesis of S-γ-[(4-trifluoromethyl)-phenoxy]benzenepropanamine-[1-14C] maleate, an important metabolite of fluoxetine hydrochloride" (in en). Journal of Labelled Compounds and Radiopharmaceuticals 31 (2): 119–124. 1992. doi:10.1002/jlcr.2580310207.
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