Levomilnacipran

Levomilnacipran
Clinical data
Trade namesFetzima
AHFS/Drugs.comMonograph
Routes of
administration		By mouth (capsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability92%[5]
Protein binding22%[6]
MetabolismHepatic (primarily by CYP3A4)[7]
Elimination half-life12 hours[7]
ExcretionKidney[7]
Identifiers
  • (1S,2R)-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@]1(C[C@H]1CN)C2=CC=CC=C2
  • InChI=1S/C15H22N2O/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12/h5-9,13H,3-4,10-11,16H2,1-2H3/t13-,15+/m0/s1 ☒N
  • Key:GJJFMKBJSRMPLA-DZGCQCFKSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Levomilnacipran (brand name Fetzima) is an antidepressant which was approved in the United States in 2013 for the treatment of major depressive disorder (MDD) in adults.[5] It is the levorotatory enantiomer of milnacipran, and has similar effects and pharmacology, acting as a serotonin–norepinephrine reuptake inhibitor (SNRI).[8][9]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
  4. ^ "Health Canada New Drug Authorizations: 2015 Highlights". Health Canada. 4 May 2016. Retrieved 7 April 2024.
  5. ^ a b "Fetzima (levomilnacipran) Extended-Release Capsules, for Oral Use. Full Prescribing Information". Forest Pharmaceuticals, Inc. Subsidiary of Forest Laboratories, Inc. St. Louis, MO 63045 USA. July 2014. Retrieved 2 September 2016.
  6. ^ Cite error: The named reference SchatzbergNemeroff2017 was invoked but never defined (see the help page).
  7. ^ a b c Cite error: The named reference Stahl2017 was invoked but never defined (see the help page).
  8. ^ Myers C (22 December 2008). "Pierre Fabre Medicament and Forest Laboratories to Collaborate on Development and Commercialization of F2695 for Depression". FierceBiotech.
  9. ^ 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): 166–171. doi:10.1007/bf03189334. PMID 9725476. S2CID 24621735.