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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

Targets

Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Which bioequivalence study for a racemic drug? Application to milnacipran.
1998 Apr-Jun
Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors.
2008 Jun 1
28th Annual JPMorgan Healthcare Conference--Forest Laboratories and Icagen.
2010 Mar
Levomilnacipran (F2695), a norepinephrine-preferring SNRI: profile in vitro and in models of depression and anxiety.
2013 Jul
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?
2013 Nov
Levomilnacipran extended release: first global approval.
2013 Sep
Patents

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
Name Type Language
LEVOMILNACIPRAN
INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
(1S,2R)-MILNACIPRAN
Common Name English
F2695
Code English
F 2695
Code English
LEVOMILNACIPRAN [WHO-DD]
Common Name English
MILNACIPRAN, (1S,2R)-
Common Name English
F-2695
Code English
LEVOMILNACIPRAN [VANDF]
Common Name English
LEVOMILNACIPRAN [INN]
Common Name English
LEVOMILNACIPRAN [USAN]
Common Name English
CYCLOPROPANECARBOXAMIDE, 2-(AMINOMETHYL)-N,N-DIETHYL-1-PHENYL-, (1S,2R)-
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175749
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
Code System Code Type Description
WIKIPEDIA
LEVOMILNACIPRAN
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY
RXCUI
1433212
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL99946
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY
EVMPD
SUB40892
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY
IUPHAR
7435
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY
CAS
96847-54-0
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY
INN
8740
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY
LactMed
96847-54-0
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY
PUBCHEM
6917779
Created by admin on Mon Oct 21 23:54:23 UTC 2019 , Edited by admin on Mon Oct 21 23:54:23 UTC 2019
PRIMARY