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Title: Levomilnacipran  
Author: World Heritage Encyclopedia
Language: English
Subject: Cimoxatone, Metfendrazine, Cianopramine, Mebanazine, Octamoxin
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Systematic (IUPAC) name
Clinical data
Trade names Fetzima
Pregnancy cat.
Legal status
  • Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 92%[1]
Protein binding 22%
Metabolism Hepatic (primarily by CYP3A4)
Half-life 12 hours
Excretion Renal
CAS number  YesY
175131-60-9 (hydrochloride)
ATC code None
ChemSpider  N
Chemical data
Formula C15H22N2O 
Mol. mass 246.348 g/mol

Levomilnacipran (brand name Fetzima) is an antidepressant approved for the treatment of major depressive disorder in the United States. It was developed by Forest Laboratories and Pierre Fabre Group, and was approved by the Food and Drug Administration in July 2013.[2] Levomilnacipran is the levo- enantiomer of milnacipran, and has similar effects and pharmacology, acting as a serotonin-norepinephrine reuptake inhibitor (SNRI).[3][4]

The FDA approved levomilnacipran in July 2013 based on the results of one 10-week phase II and four 8-week phase III clinical trials. Four of the five trials demonstrated a statistically significant superiority to placebo as measured by the Montgomery–Åsberg Depression Rating Scale. Superiority to placebo was also demonstrated by improvement in the Sheehan Disability Scale. Side effects seen more often than with placebo included nausea, dizziness, sweating, constipation, insomnia, increased heart rate and blood pressure, urinary hesitancy, erectile dysfunction and delayed ejaculation in males, vomiting, tachycardia, and palpitations.[2][5]

Relative to other SNRIs, levomilnacipran, as well as milnacipran, differ in that they are much more balanced reuptake inhibitors of serotonin and norepinephrine.[6][7][8] To demonstrate, the serotonin:norepinephrine ratios of SNRIs are as follows: venlafaxine = 30:1, duloxetine = 10:1, desvenlafaxine = 10:1, milnacipran = 1:1, and levomilnacipran = 1:2.[6] The clinical implications of more balanced elevations of serotonin and norepinephrine are unclear,[6] but may include improved effectiveness, though also increased side effects.[8][9][7]


  1. ^ "FETZIMA™ (levomilnacipran) extended-release capsules, for oral use. Prescribing Information", Forest Laboratories Inc., 2013. Revised: July 2013. [1]
  2. ^ a b Citrome L (November 2013). "Levomilnacipran for major depressive disorder: a systematic review of the efficacy and safety profile for this newly approved antidepressant--what is the number needed to treat, number needed to harm and likelihood to be helped or harmed?". Int. J. Clin. Pract. 67 (11): 1089–104.  
  3. ^ "Pierre Fabre Medicament and Forest Laboratories to Collaborate on Development and Commercialization of F2695 for Depression - FierceBiotech". 
  4. ^ Deprez D, Chassard D, Baille P, Mignot A, Ung HL, Puozzo C (1998). "Which bioequivalence study for a racemic drug? Application to milnacipran". European Journal of Drug Metabolism and Pharmacokinetics 23 (2): 166–71.  
  5. ^ Sambunaris A, Bose A, Gommoll CP, Chen C, Greenberg WM, Sheehan DV (February 2014). "A phase III, double-blind, placebo-controlled, flexible-dose study of levomilnacipran extended-release in patients with major depressive disorder". J Clin Psychopharmacol 34 (1): 47–56.  
  6. ^ a b c Sansone RA, Sansone LA (March 2014). "Serotonin norepinephrine reuptake inhibitors: a pharmacological comparison". Innov Clin Neurosci 11 (3-4): 37–42.  
  7. ^ a b Saraceni MM, Venci JV, Gandhi MA (December 2013). "Levomilnacipran (Fetzima): A New Serotonin-Norepinephrine Reuptake Inhibitor for the Treatment of Major Depressive Disorder". J Pharm Pract.  
  8. ^ a b Kasper S, Pail G (2010). "Milnacipran: a unique antidepressant?". Neuropsychiatr Dis Treat 6: 23–31.  
  9. ^ Bradley AJ, Lenox-Smith AJ (August 2013). "Does adding noradrenaline reuptake inhibition to selective serotonin reuptake inhibition improve efficacy in patients with depression? A systematic review of meta-analyses and large randomised pragmatic trials". J. Psychopharmacol. (Oxford) 27 (8): 740–58.  

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