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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22N2O
Molecular Weight 246.348
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMILNACIPRAN

SMILES

CCN(CC)C(=O)[C@]1(C[C@H]1CN)C2=CC=CC=C2

InChI

InChIKey=GJJFMKBJSRMPLA-DZGCQCFKSA-N
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

HIDE SMILES / InChI

Description

Levomilnacipran (1S, 2R/F2695) is an enantiomer of milnacipran, a serotonin/norepinephrine (5-HT/NE) reuptake inhibitor. Levomilnacipran is pharmacologically more active as compared with racemic mixture and dextromilnacipran (1R, 2S/F2696). The safety of the drug is also higher than the safety of a racemate, resulting in a beneficial impact on the therapeutic effect. Pierre Fabre and Forest Laboratories are developing levomilnacipran extended release (ER) [FETZIMA™], an enantiomer of milnacipran, for the treatment of major depressive disorder (MDD). In addition, Pierre Fabre (the originator of the compound) is developing the drug to improve recovery in patients with ischaemic stroke.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.2 nM [Ki]
92.2 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FETZIMA
Primary
FETZIMA

Cmax

ValueDoseCo-administeredAnalytePopulation
341 ng/mL
120 mg 1 times / day steady-state, oral
LEVOMILNACIPRAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
5196 ng × h/mL
120 mg 1 times / day steady-state, oral
LEVOMILNACIPRAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
12 h
120 mg 1 times / day steady-state, oral
LEVOMILNACIPRAN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
78%
120 mg 1 times / day steady-state, oral
LEVOMILNACIPRAN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Initial Treatment of Major Depressive Disorder: The recommended dose range for FETZIMA (levomilnacipran extended-release capsules) is 40 mg to 120 mg once daily. FETZIMA should be initiated at 20 mg once daily for 2 days and then increased to 40 mg once daily.
Route of Administration: Oral
In Vitro Use Guide
Levomilnacipran inhibits norepinephrine and serotonin reuptake in rat hypothalamic synaptosomes with IC50 values of 15 and 46 nM, respectively