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Viloxazine

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Title: Viloxazine  
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Subject: Thozalinone, Ciclazindol, Mazindol, Cimoxatone, Metfendrazine
Collection: Bicyclic Antidepressants, Heterocyclic Compounds, Morpholines, Phenol Ethers
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Viloxazine

Viloxazine
Systematic (IUPAC) name
(RS)-2-[(2-ethoxyphenoxy)methyl]morpholine
Clinical data
Legal status
  • Not a controlled substance
Routes Oral, intravenous (infusion)
Pharmacokinetic data
Half-life 2-5 hours
Excretion Renal
Identifiers
CAS number  N 46817-91-8
35604-67-2 (HCl salt)
ATC code N06
PubChem
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEMBL  YesY
Chemical data
Formula C13H19NO3 
Mol. mass 237.295 g/mol
 N   

Viloxazine (Vivalan, Emovit, Vivarint, Vicilan) is a bicyclic antidepressant morpholine derivative that acts as a selective norepinephrine reuptake inhibitor (NRI). It produces a marked stimulant effect that is similar to the amphetamines, except without any signs of dependence.[1] It is a racemic compound with two stereoisomers, the (S)-(–)-isomer being five times as pharmacologically active as the (R)-(+)-isomer.

Contents

  • Uses 1
    • Approved 1.1
    • Unapproved/off-Label/investigational 1.2
  • Mechanism of action 2
  • Side effects 3
  • Drug interactions 4
  • See also 5
  • References 6

Uses

Approved

Viloxazine hydrochloride was approved in Italy, Belgium, England, Ireland, Germany, Portugal, Spain, the former Yugoslavia, France, Slovakia, for the treatment of clinical depression.

Unapproved/off-Label/investigational

Viloxazine has undergone two randomized controlled trials for nocturnal enuresis (bedwetting) in children, both of those times versus imipramine., By 1990, it was seen as a less cardiotoxic alternative to imipramine, and to be especially effective in heavy sleepers.

In narcolepsy, viloxazine has been shown to suppress auxiliary symptoms such as cataplexy and also abnormal sleep-onset REM without really improving daytime somnolence.

In a cross-over trial (56 participants) viloxazine significantly reduced EDS and cataplexy. {ref Vignatelli L, D'Alessandro R, Candelise L. Antidepressant drugs for narcolepsy. Cochrane Database of Systematic Reviews 2007, Issue 4. Art. No.: CD003724. doi:10.1002/14651858.CD003724.pub3}

Viloxazine has also been studied for the treatment of alcoholism, with some success.

While viloxazine may be effective in clinical depression, it did relatively poorly in a double-blind randomized controlled trial versus amisulpride in the treatment of dysthymia, according to Leon and colleagues at the University of Valle in Colombia.

Mechanism of action

In 1976, Lippman and Pugsley reported that viloxazine, like imipramine, inhibited norepinephrine reuptake in the hearts of rats and mice; unlike imipramine, (or desipramine or amitriptyline, for that matter) it did not block reuptake of norepinephrine in either the medullae or the hypothalami of rats. As for serotonin, while its reuptake inhibition was comparable to that of desipramine (i.e., very weak), viloxazine did potentiate serotonin-mediated brain functions in a manner similar to amitriptyline and imipramine, which are relatively potent inhibitors of serotonin reuptake. Unlike any of the other drugs tested, it did not exhibit any anticholinergic effects.

It is also known to up-regulate GABAB receptors in the frontal cortex.

Side effects

Side effects include nausea, vomiting, insomnia, loss of appetite, increased erythrocyte sedimentation, EKG and EEG anomalies, epigastric pain, diarrhea, constipation, vertigo, orthostatic hypotension, edema of the lower extremities, dysarthria, tremor, psychomotor agitation, mental confusion, inappropriate secretion of antidiuretic hormone, increased transaminases, seizure, (there were three cases worldwide, and most animal studies (and clinical trials that included epilepsy patients) indicated the presence of anticonvulsant properties, so is not completely contraindicated in epilepsy,) and increased libido.

Drug interactions

Viloxazine is known to increase plasma levels of phenytoin by an average of 37%. It is also known to significantly increase plasma levels of theophylline and decrease its clearance from the body, sometimes resulting in accidental overdose of theophylline.

See also

References

  1. ^ Pinder, RM; Brogden, RN; Speight, TM; Avery, GS (June 1977). "Viloxazine: a review of its pharmacological properties and therapeutic efficacy in depressive illness.". Drugs 13 (6): 401–21.  
  1. ^ "SID 180462-- PubChem Substance Summary". Retrieved 5 November 2005. 
  2. ^ "MEDLINE subject headings for Viloxazine". Retrieved 5 November 2005. 
  3. ^ Case DE, Reeves PR (February 1975). "The disposition and metabolism of I.C.I. 58,834 (viloxazine) in humans". Xenobiotica 5 (2): 113–29.  
  4. ^ Bouchard JM, Strub N, Nil R (October 1997). "Citalopram and viloxazine in the treatment of depression by means of slow drop infusion. A double-blind comparative trial". Journal of Affective Disorders 46 (1): 51–8.  
  5. ^ 【合法】個人輸入代行薬【未認可】 (The relevant section is English)
  6. ^ Müller-Oerlinghausen B, Rüther E (July 1979). "Clinical profile and serum concentration of viloxazine as compared to amitriptyline". Pharmakopsychiatrie, Neuro-Psychopharmakologie 12 (4): 321–37.  
  7. ^ Danchev ND, Rozhanets VV, Zhmurenko LA, Glozman OM, Zagorevskiĭ VA (May 1984). "Behavioral and radioreceptor analysis of viloxazine stereoisomers" [Behavioral and radioreceptor analysis of viloxazine stereoisomers]. Biulleten' Eksperimental'noĭ Biologii i Meditsiny (in Russian) 97 (5): 576–8.  
  8. ^ AstraZeneca Slovensko (2000). "VIVALAN tbl obd". Retrieved 2005-11-05. 
  9. ^ AstraZeneca International (2003). "Vivalan (viloxazine hydrochloride)". Retrieved 2005-11-06. 
  10. ^ Attenburrow AA, Stanley TV, Holland RP (January 1984). "Nocturnal enuresis: a study". The Practitioner 228 (1387): 99–102.  
  11. ^ Yurdakök M, Kinik E, Güvenç H, Bedük Y (1987). "Viloxazine versus imipramine in the treatment of enuresis".  
  12. ^ Libert MH (1990). "The use of viloxazine in the treatment of primary enuresis" [The use of viloxazine in the treatment of primary enuresis]. Acta Urologica Belgica (in French) 58 (1): 117–22.  
  13. ^ Guilleminault C, Mancuso J, Salva MA, et al. (1986). "Viloxazine hydrochloride in narcolepsy: a preliminary report". Sleep 9 (1 Pt 2): 275–9.  
  14. ^ Mitler MM, Hajdukovic R, Erman M, Koziol JA (January 1990). "Narcolepsy". Journal of Clinical Neurophysiology 7 (1): 93–118.  
  15. ^ Altamura AC, Mauri MC, Girardi T, Panetta B (1990). "Alcoholism and depression: a placebo controlled study with viloxazine". International Journal of Clinical Pharmacology Research 10 (5): 293–8.  
  16. ^ León CA, Vigoya J, Conde S, Campo G, Castrillón E, León A (March 1994). "Comparison of the effect of amisulpride and viloxazine in the treatment of dysthymia" [Comparison of the effect of amisulpride and viloxazine in the treatment of dysthymia]. Acta Psiquiátrica Y Psicológica de América Latina (in Spanish) 40 (1): 41–9.  
  17. ^ Lippman W, Pugsley TA (August 1976). "Effects of viloxazine, an antidepressant agent, on biogenic amine uptake mechanisms and related activities". Canadian Journal of Physiology and Pharmacology 54 (4): 494–509.  
  18. ^ Lippman and Pugsley, 1976.see
  19. ^ Lloyd KG, Thuret F, Pilc A (October 1985). "Upregulation of gamma-aminobutyric acid (GABA) B binding sites in rat frontal cortex: a common action of repeated administration of different classes of antidepressants and electroshock". The Journal of Pharmacology and Experimental Therapeutics 235 (1): 191–9.  
  20. ^ Edwards JG, Glen-Bott M (September 1984). "Does viloxazine have epileptogenic properties?". Journal of Neurology, Neurosurgery, and Psychiatry 47 (9): 960–4.  
  21. ^ Chebili S, Abaoub A, Mezouane B, Le Goff JF (1998). "Antidepressants and sexual stimulation: the correlation" [Antidepressants and sexual stimulation: the correlation]. L'Encéphale (in French) 24 (3): 180–4.  
  22. ^ Pisani F, Fazio A, Artesi C, et al. (February 1992). "Elevation of plasma phenytoin by viloxazine in epileptic patients: a clinically significant drug interaction". Journal of Neurology, Neurosurgery, and Psychiatry 55 (2): 126–7.  
  23. ^ Perault MC, Griesemann E, Bouquet S, Lavoisy J, Vandel B (September 1989). "A study of the interaction of viloxazine with theophylline". Therapeutic Drug Monitoring 11 (5): 520–2.  
  24. ^ Laaban JP, Dupeyron JP, Lafay M, Sofeir M, Rochemaure J, Fabiani P (1986). "Theophylline intoxication following viloxazine induced decrease in clearance". European Journal of Clinical Pharmacology 30 (3): 351–3.  
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