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Seproxetine

From Wikipedia, the free encyclopedia
(Redirected fromNorfluoxetine)
SSRI drug and metabolite of fluoxetine
Pharmaceutical compound
Seproxetine
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
Eliminationhalf-life4–16 days
Identifiers
  • (S)-3-Phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC16H16F3NO
Molar mass295.305 g·mol−1

Seproxetine, also known as(S)-norfluoxetine, is aselective serotonin reuptake inhibitor (SSRI).[1][2] It is theSenantiomer of norfluoxetine, the mainactive metabolite of the widely usedantidepressantfluoxetine;[3] it is nearly 4 times more selective for stimulatingneurosteroid synthesis relative to serotonin reuptake inhibition than fluoxetine.[4] It is formed through thedemethylation, or removal of amethyl group, of fluoxetine.[5] Seproxetine is both an inhibitor ofserotonin anddopamine transporters,5-HT2A and5-HT2C receptors.[6] It was being investigated byEli Lilly and Company as an antidepressant; however, it inhibited theKvLQT1 protein, which is responsible for the management of theQT 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 theR enantiomer of norfluoxetine.[8]

References

[edit]
  1. ^ab"Seproxetine".DrugBank. University of Alberta. Archived fromthe original on 31 October 2020. Retrieved10 August 2016.
  2. ^de Maat MM, Huitema AD, Mulder JW, Meenhorst PL, van Gorp EC, Mairuhu AT, Beijnen JH (1 October 2003). "Drug Interaction of Fluvoxamine and Fluoxetine with Nevirapine in HIV-1-Infected Individuals".Clinical Drug Investigation.23 (10):629–637.doi:10.2165/00044011-200323100-00002.PMID 17535078.S2CID 25958396.
  3. ^Anderson IM, Edwards JG (2001)."Guidelines for choice of selective serotonin reuptake inhibitor in depressive illness".Advances in Psychiatric Treatment.7 (3):170–180.doi:10.1192/apt.7.3.170.ISSN 1355-5146.
  4. ^Pinna G, Costa E, Guidotti A (February 2009)."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.doi:10.1016/j.coph.2008.12.006.PMC 2670606.PMID 19157982.
  5. ^Alvén Fimmerstad T (2022).Could fluorinated pharmaceuticals have an impact on the EOF amount in human blood? (degree of Bachelor thesis). Örebro University.
  6. ^Al-Humaidi JY, Refat MS (15 June 2021)."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.doi:10.1016/j.molliq.2021.115831.ISSN 0167-7322.S2CID 233773168.
  7. ^"Seproxetine".Inxight Drugs. National Center for Advancing Translational Sciences (NCATS).Archived from the original on 20 April 2023. Retrieved20 April 2023.
  8. ^Wheeler WJ (1992). "An efficient synthesis of S-γ-[(4-trifluoromethyl)-phenoxy]benzenepropanamine-[1-14C] maleate, an important metabolite of fluoxetine hydrochloride".Journal of Labelled Compounds and Radiopharmaceuticals.31 (2):119–124.doi:10.1002/jlcr.2580310207.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
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TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
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Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
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5-HT1ARTooltip 5-HT1A receptoragonists
GABAARTooltip GABAA receptorPAMsTooltip positive allosteric modulators
Gabapentinoids
(α2δVDCCblockers)
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(Antiadrenergics)
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
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