milnacipran   Click here for help

GtoPdb Ligand ID: 7436

Synonyms: Savella®
Approved drug
milnacipran is an approved drug (FDA (2009))
Compound class: Synthetic organic
Comment: Milnacipran is approved as a racemic mixture of enantiomers. We show the non-isomeric structure to represent the mixture.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: milnacipran

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 NCC1CC1(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
1. Arnold LM, Gendreau RM, Palmer RH, Gendreau JF, Wang Y. (2010)
Efficacy and safety of milnacipran 100 mg/day in patients with fibromyalgia: results of a randomized, double-blind, placebo-controlled trial.
Arthritis Rheum, 62 (9): 2745-56. [PMID:20496365]
2. Moret C, Briley M. (2006)
Antidepressants in the treatment of fibromyalgia.
Neuropsychiatr Dis Treat, 2 (4): 537-48. [PMID:19412502]
3. Van Orden LJ, Van Dyke PM, Saito DR, Church TJ, Chang R, Smith JA, Martin WJ, Jaw-Tsai S, Stangeland EL. (2013)
A novel class of 3-(phenoxy-phenyl-methyl)-pyrrolidines as potent and balanced norepinephrine and serotonin reuptake inhibitors: synthesis and structure-activity relationships.
Bioorg Med Chem Lett, 23 (5): 1456-61. [PMID:23347683]