levomilnacipran   Click here for help

GtoPdb Ligand ID: 7435

Synonyms: F-2695 | Fetzima®
Approved drug
levomilnacipran is an approved drug (FDA (2013))
Compound class: Synthetic organic
Comment: Levomilnacipran is the active enantiomer of milnacipran. [2]. It is a selective serotonin and norepinephrine reuptake inhibitor antidepressant (SNRI).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: levomilnacipran

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 46.33
Molecular weight 246.17
XLogP 1.91
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES NCC1CC1(c1ccccc1)C(=O)N(CC)CC
Isomeric SMILES NC[C@@H]1C[C@]1(c1ccccc1)C(=O)N(CC)CC
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
1. Citrome L. (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. [PMID:24016209]
2. Deprez D, Chassard D, Baille P, Mignot A, Ung HL, Puozzo C. (1998)
Which bioequivalence study for a racemic drug? Application to milnacipran.
Eur J Drug Metab Pharmacokinet, 23 (2): 166-71. [PMID:9725476]
3. Vickers T, Dyck B, Tamiya J, Zhang M, Jovic F, Grey J, Fleck BA, Aparicio A, Johns M, Jin L et al.. (2008)
Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors.
Bioorg Med Chem Lett, 18 (11): 3230-5. [PMID:18468895]