Levomilnacipran

Levomilnacipran
Clinical data
Trade names	Fetzima
AHFS/Drugs.com	Monograph
MedlinePlus	a613048
License data	US DailyMed: Levomilnacipran;
Routes of; administration	By mouth
ATC code	N06AX28 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); CA: ℞-only; US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	92%
Protein binding	22%
Metabolism	Liver (primarily by CYP3A4)
Elimination half-life	12 hours
Excretion	Kidney
Identifiers
	IUPAC name (1S,2R)-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide;
CAS Number	96847-54-0 ; HCl: 175131-60-9 ;
PubChem CID	6917779;
IUPHAR/BPS	7435;
DrugBank	DB08918;
ChemSpider	5293005 ;
UNII	UGM0326TXX; HCl: 371U2ZK31U ;
KEGG	D10072 ;
CompTox Dashboard (EPA)	DTXSID701025167 ;
Chemical and physical data
Formula	C15H22N2O
Molar mass	246.354 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)[C@]1(C[C@H]1CN)C2=CC=CC=C2;
	InChI 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 ; Key:GJJFMKBJSRMPLA-DZGCQCFKSA-N ;
	(what is this?) (verify)

Levomilnacipran, sold under the brand name Fetzima, is an antidepressant, used for the treatment of major depressive disorder in adults.^[4] It is the levorotatory enantiomer of milnacipran, and has similar effects and pharmacology, acting as a serotonin–norepinephrine reuptake inhibitor.^[7]^[8]

Levomilnacipran was approved for medical use in the United States in July 2013.^[9]

^ Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
^ "Health Canada New Drug Authorizations: 2015 Highlights". Health Canada. 4 May 2016. Retrieved 7 April 2024.
^ ^a ^b ^c "Fetzima- levomilnacipran hydrochloride capsule, extended release; Fetzima- levomilnacipran hydrochloride kit". DailyMed. 19 April 2024. Retrieved 17 April 2025.
^ Cite error: The named reference SchatzbergNemeroff2017 was invoked but never defined (see the help page).
^ ^a ^b ^c Cite error: The named reference Stahl2017 was invoked but never defined (see the help page).
^ Myers C (22 December 2008). "Pierre Fabre Medicament and Forest Laboratories to Collaborate on Development and Commercialization of F2695 for Depression". FierceBiotech.
^ 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.
^ "Drug Approval Package: Fetzima (levomilnacipran) Extended-Release Capsules NDA #204168". U.S. Food and Drug Administration (FDA). 14 March 2014. Archived from the original on 29 June 2015. Retrieved 17 April 2025.

[1] Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[2] "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.

[3] "Health Canada New Drug Authorizations: 2015 Highlights". Health Canada. 4 May 2016. Retrieved 7 April 2024.

[Fetzima_FDA_label-4] "Fetzima- levomilnacipran hydrochloride capsule, extended release; Fetzima- levomilnacipran hydrochloride kit". DailyMed. 19 April 2024. Retrieved 17 April 2025.

[SchatzbergNemeroff2017-5] Cite error: The named reference SchatzbergNemeroff2017 was invoked but never defined (see the help page).

[Stahl2017-6] Cite error: The named reference Stahl2017 was invoked but never defined (see the help page).

[urlPierre_Fabre_Medicament_and_Forest_Laboratories_to_Collaborate_on_Development_and_Commercialization_of_F2695_for_Depression_-_FierceBiotech-7] Myers C (22 December 2008). "Pierre Fabre Medicament and Forest Laboratories to Collaborate on Development and Commercialization of F2695 for Depression". FierceBiotech.

[pmid9725476-8] 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.

[Fetzima_Drug_Approval_Package-9] "Drug Approval Package: Fetzima (levomilnacipran) Extended-Release Capsules NDA #204168". U.S. Food and Drug Administration (FDA). 14 March 2014. Archived from the original on 29 June 2015. Retrieved 17 April 2025.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]