U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22N2O.ClH
Molecular Weight 282.809
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMILNACIPRAN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=XNCDYJFPRPDERF-NQQJLSKUSA-N
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/t13-,15+;/m0./s1

HIDE SMILES / InChI
Molecular Formula C15H22N2O
Molecular Weight 246.348
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24000002 | https://www.ncbi.nlm.nih.gov/pubmed/27180420

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

2009
364
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 11.2 nM [Ki]
Inhibitor
8504
 92.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
FETZIMA

Approved Use

FETZIMA (levomilnacipran) extended-release capsules is a serotonin and norepinephrine reuptake inhibitor (SNRI) indicated for the treatment of Major Depressive Disorder (MDD) in adults. FETZIMA is not approved for the management of fibromyalgia, and its efficacy and safety have not been established for that use.

Launch Date

2013
Primary
Phase III
665
FETZIMA

Approved Use

FETZIMA (levomilnacipran) extended-release capsules is a serotonin and norepinephrine reuptake inhibitor (SNRI) indicated for the treatment of Major Depressive Disorder (MDD) in adults. FETZIMA is not approved for the management of fibromyalgia, and its efficacy and safety have not been established for that use.

Launch Date

2013
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
341 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204168s000lbl.pdf
120 mg 1 times / day steady-state, oral
dose: 120 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LEVOMILNACIPRAN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5196 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204168s000lbl.pdf
120 mg 1 times / day steady-state, oral
dose: 120 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LEVOMILNACIPRAN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204168s000lbl.pdf
120 mg 1 times / day steady-state, oral
dose: 120 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LEVOMILNACIPRAN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
78%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204168s000lbl.pdf
120 mg 1 times / day steady-state, oral
dose: 120 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LEVOMILNACIPRAN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Disc. AE: Angina pectoris, Extrasystoles supraventricular...
AEs leading to
discontinuation/dose reduction:
Angina pectoris (0.12%)
Extrasystoles supraventricular (0.12%)
Encephalopathy (0.12%)
Mania (0.12%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Disc. AE: Tachycardia, Nausea...
AEs leading to
discontinuation/dose reduction:
Tachycardia
Nausea
Insomnia
Agitation
Constipation
Hypertension
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Disc. AE: Suicidal ideation, Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Serotonin syndrome
Blood pressure increased
Heart rate increased
Bleeding
Angle closure glaucoma
Urinary hesitation
Urinary retention
Mania
Hypomania
Hyponatremia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea (1.5%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Angina pectoris 0.12%
Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Encephalopathy 0.12%
Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Extrasystoles supraventricular 0.12%
Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Mania 0.12%
Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Agitation Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Constipation Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Hypertension Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Insomnia Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Nausea Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Tachycardia Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
unhealthy, 18-80
Health Status: unhealthy
Age Group: 18-80
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Angle closure glaucoma Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Bleeding Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Blood pressure increased Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Heart rate increased Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Hypomania Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Hyponatremia Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Mania Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Serotonin syndrome Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Suicidal ideation Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Urinary hesitation Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Urinary retention Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Nausea 1.5%
Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252

inducer
1087
substrate
1193

inhibitor
2438

inducer
440
substrate
1388

inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057

CYP1A2
2153

CYP2A6
879

CYP2C8
1057

CYP2E1
1060

CYP3A5
136

P-gp
1741

BCRP
910

OAT1
725

OAT3
747

OATP1B1
1079

OATP1B3
961

OCT2
779
CYP2C8
810

CYP2C19
1119

CYP2J2
71

CYP1A2
1197

CYP2A6
626

CYP2B6
776

CYP2E1
729

P-gp
2052

BCRP
697

OAT1
395

OAT3
391

OATP1B1
503

OATP1B3
435

OCT2
434
CYP1A2
832

CYP2C19
329

CYP3A5
92

UGT1A6
34
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no
CYP1A2
2333
 no
CYP2A6
911
 no
CYP2C19
2141
 no
CYP2C19
2141
 no
CYP2C8
1117
 no
CYP2C9
2497
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP2E1
1146
 no
CYP3A4
2633
 no
CYP3A4
2633
 no
CYP3A5
201
 no
CYP3A5
201
 no
UGT1A6
171
 no
BCRP
985
 not significant
OAT1
730
 not significant
OAT3
749
 not significant
OATP1B1
1095
 not significant
OATP1B3
970
 not significant
OCT2
782
 not significant
P-gp
1932
 weak [IC50 423 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1197
 low
CYP2A6
626
 low
CYP2B6
776
 low
CYP2C9
1193
 low
CYP2E1
729
 low
CYP3A4
1946
 major
yes (co-administration study)
Comment: Ketoconazole (inhibitor) increased levomilnacipran exposure (AUC) by about 50%; dose adjustment of drug not recommeded whe co-administered with CYP3A4 inducers (carbamazepine) and substrate (alprazolam);
Page: 39.0
CYP2C19
1119
 minor
CYP2C8
810
 minor
CYP2D6
1388
 minor
CYP2J2
71
 minor
BCRP
697
 no
OAT1
395
 no
OAT3
391
 no
OATP1B1
503
 no
OATP1B3
435
 no
OCT2
434
 no
P-gp
2052
 weak
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0004BY
1PlusChem LLC
1P0020LY
A2B Chem
AA04814
AA Blocks
AA0003SI
ABI Chem
AC1OCEN8
AbovChem LLC
HY-B0168B
AChemBlock
L14973
Achemtek
0102-013376
http://www.achemtek.com/96847-55-1
AK Scientific
G420
AK Scientific
J10386
Ambeed
A436777
Angene
AGN-PC-00LGPD
ApexBio Technology
B2112
AstaTech
43231
AstaTech
C13985
AstaTech
C73344
AstaTech
Y10009
BLD Pharm
BD01272635
http://www.bldpharm.com/products/96847-54-0.html
BOC Sciences
101152-94-7
BOC Sciences
175131-60-9
BOC Sciences
96847-54-0
Bosche Scientific
M4677
Chem Scene
CS-4972
Chemieliva Pharmaceutical Co., Ltd
PBCM1487292
Combi-Blocks
QA-1133
Combi-Blocks
QM-9767
Combi-Blocks
QV-0092
Compound Cloud
6917778
Compound Cloud
6917779
eMolecules
300422252
eMolecules
300424416
eMolecules
31706396
eMolecules
44838574
eMolecules
89941005
eNovation Chemicals
D546565
http://www.enovationchem.com/productDetails.asp?productID=D546565
Fluorochem
506367
Hairui
HR101536
Hairui
HR143593
Hangzhou APIChem Technology
AC-1532
KeyOrganics
AS-12868
Lab Network
LN01300009
Lan Pharmatech
LQT-A00044
mcule
MCULE-1343334533
mcule
MCULE-1701139308
mcule
MCULE-3183239121
mcule
MCULE-7769814944
mcule
MCULE-9803369943
MedChem Express
HY-B0168B
Molcore
MC106953
MolPort
MolPort-006-666-270
MolPort
MolPort-019-939-251
MolPort
MolPort-042-676-060
MuseChem
I005512
MuseChem
R047491
PI Chemicals
PI-39268
Ryan Scientific
Etonogestrel
Ryan Scientific
Iloperidone
Selleck Chemicals
S3140
Selleck Chemicals
S5693
Smolecule
S532973
http://www.smolecule.com/products/s532973
Synblock Inc
SB17447
http://www.synblock.com/product/96847-54-0.html
SynQuest
1040335
SynQuest
80573
TargetMol
T1189
TargetMol
T2594
Tetrahedron
TS34485
THE BioTek
bt-272644
https://www.thebiotek.com/product/inhibitors/bt-272644
Toronto Research Chemicals
KIT0185
Toronto Research Chemicals
M344595
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.
PH-5139AP
ZINC
ZINC000000000506
http://zinc15.docking.org/substances/ZINC000000000506
PubMed

PubMed

TitleDatePubMed
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?
2013-11
Levomilnacipran extended release: first global approval.
2013-09
Levomilnacipran (F2695), a norepinephrine-preferring SNRI: profile in vitro and in models of depression and anxiety.
2013-07
28th Annual JPMorgan Healthcare Conference--Forest Laboratories and Icagen.
2010-03
Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors.
2008-06-01
Which bioequivalence study for a racemic drug? Application to milnacipran.
1998-09-02
Patents

Patents

US20140343322
2
US20150148424
2
WO2015044962A1
2

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
Substance Class Chemical
Created
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on Mon Mar 31 20:04:24 GMT 2025
Edited
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on Mon Mar 31 20:04:24 GMT 2025
Record UNII
371U2ZK31U
Record Status Validated (UNII)
Record Version
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Name Type Language
FETZIMA
Preferred Name English
LEVOMILNACIPRAN HYDROCHLORIDE
ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
LEVOMILNACIPRAN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
F-2695 HYDROCHLORIDE
Code English
MILNACIPRAN HYDROCHLORIDE, (1S,2R)-
Common Name English
(1S,2R)-MILNACIPRAN HYDROCHLORIDE
Common Name English
Levomilnacipran hydrochloride [WHO-DD]
Common Name English
F 2695 HYDROCHLORIDE
Code English
F2695 HYDROCHLORIDE
Code English
CYCLOPROPANECARBOXAMIDE, 2-(AMINOMETHYL)-N,N-DIETHYL-1-PHENYL-, HYDROCHLORIDE (1:1), (1S,2R)-
Common Name English
LEVOMILNACIPRAN HYDROCHLORIDE [USAN]
Common Name English
Code System Code Type Description
RXCUI
1433211
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL99946
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
NCI_THESAURUS
C166646
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
EVMPD
SUB130559
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
DRUG BANK
DBSALT000107
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
DAILYMED
371U2ZK31U
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID801026201
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
PUBCHEM
6917778
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
SMS_ID
100000156651
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
CAS
175131-60-9
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
USAN
YY-41
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
FDA UNII
371U2ZK31U
Created by admin on Mon Mar 31 20:04:24 GMT 2025 , Edited by admin on Mon Mar 31 20:04:24 GMT 2025
PRIMARY
Related Record Type Details
Structure of LEVOMILNACIPRAN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LEVOMILNACIPRAN
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