Milnacipran hydrochlorideProduct ingredient for Milnacipran

Name
Milnacipran hydrochloride
Drug Entry
Milnacipran

Milnacipran is a selective serotonin and norepinephrine reuptake inhibitor (SNRI) and like many agents in this category was originally developed for and continues to be approved and indicated for the treatment of depression 27,28,15,21. Furthermore, in 2009 the US FDA approved milnacipran for the additional indication of treating fibromyalgia 26, although other regional regulatory authorities like the EMA, among others, have not yet approved the agent for such treatment, citing lack of robust evidence of efficacy, insufficient demonstration of maintenance of effect, and other concerns 27,28. Nevertheless, milnacipran demonstrates a somewhat unique characteristic among SNRIs to elicit a relatively balanced reuptake inhibition of both serotonin and noradrenaline, with a somewhat increased preference for noradrenaline reuptake inhibition - which is potentially a point of interest given the plausible proposal that noradrenaline plays an important role in the mitigation of pain signals in the descending inhibitory pain pathways in the brain and spinal cord 14,18,19.

Moreover, recent research has shown that the levorotatory enantiomer of milnacipran, levomilnacipran, may have the capacity to inhibit the activity of beta-site amyloid precursor protein cleaving enzyme-1 (BACE-1), which has investigationally been associated with β-amyloid plaque formation - making the agent a possible course of treatment for Alzheimer's disease 22.

Accession Number
DBSALT000119
Structure
Synonyms
Milnacipran HCl
UNII
RNZ43O5WW5
CAS Number
101152-94-7
Weight
Average: 282.81
Monoisotopic: 282.1498911
Chemical Formula
C15H23ClN2O
InChI Key
XNCDYJFPRPDERF-UHFFFAOYSA-N
InChI
InChI=1S/C15H22N2O.ClH/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;1H
IUPAC Name
2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide hydrochloride
SMILES
Cl.CCN(CC)C(=O)C1(CC1CN)C1=CC=CC=C1
PubChem Compound
55480
ChemSpider
10771177
ChEBI
31854
ChEMBL
CHEMBL4297064
Wikipedia
Milnacipran
Predicted Properties
PropertyValueSource
Water Solubility1.23 mg/mLALOGPS
logP1.72ALOGPS
logP1.42Chemaxon
logS-2.3ALOGPS
pKa (Strongest Basic)9.83Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area46.33 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity73.81 m3·mol-1Chemaxon
Polarizability28.25 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon