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

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
359
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 11.2 nM [Ki]
Inhibitor
8297
 92.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
656
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 (max)
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
Page: p.766
unhealthy, 18-80
n = 825
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 825
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Page: p.766
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
Page: p.766
120 mg 1 times / day multiple, oral (max)
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
Page: p.52
unhealthy, 18-80
n = 217
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 217
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
Disc. AE: Tachycardia, Nausea...
AEs leading to
discontinuation/dose reduction:
Tachycardia
Nausea
Insomnia
Agitation
Constipation
Hypertension
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
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
Page: p.22
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.22
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.22
120 mg 1 times / day multiple, oral (max)
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
Page: p.12
unhealthy
n = 1583
Health Status: unhealthy
Condition: Major Depressive Disorder
Population Size: 1583
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.12
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea (1.5%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.12
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
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
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Angina pectoris 0.12%
Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.766
unhealthy, 18-80
n = 825
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 825
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Page: p.766
Encephalopathy 0.12%
Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.766
unhealthy, 18-80
n = 825
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 825
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Page: p.766
Extrasystoles supraventricular 0.12%
Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.766
unhealthy, 18-80
n = 825
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 825
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Page: p.766
Mania 0.12%
Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.766
unhealthy, 18-80
n = 825
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 825
Sources:
https://pubmed.ncbi.nlm.nih.gov/23999912
Page: p.766
Agitation Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.52
unhealthy, 18-80
n = 217
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 217
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
Constipation Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.52
unhealthy, 18-80
n = 217
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 217
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
Hypertension Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.52
unhealthy, 18-80
n = 217
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 217
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
Insomnia Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.52
unhealthy, 18-80
n = 217
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 217
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
Nausea Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.52
unhealthy, 18-80
n = 217
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 217
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
Tachycardia Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.52
unhealthy, 18-80
n = 217
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: 18-80
Sex: M+F
Population Size: 217
Sources:
https://pubmed.ncbi.nlm.nih.gov/24172209
Page: p.52
Nausea 1.5%
Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.12
unhealthy
n = 1583
Health Status: unhealthy
Condition: Major Depressive Disorder
Population Size: 1583
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.12
Angle closure glaucoma Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Bleeding Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Blood pressure increased Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Heart rate increased Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Hypomania Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Hyponatremia Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Mania Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Serotonin syndrome Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Suicidal ideation Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Urinary hesitation Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Urinary retention Disc. AE
120 mg 1 times / day multiple, oral (max)
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major Depressive Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/204168s004lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587

inducer
781
substrate
1037

inhibitor
1767

inducer
389
substrate
1217

inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
1478

CYP1A2
1524

CYP2A6
707

CYP2C8
911

CYP2E1
882

CYP3A5
73

P-gp
1461

BCRP
699

OAT1
599

OAT3
642

OATP1B1
788

OATP1B3
706

OCT2
647
CYP2C8
693

CYP2C19
991

CYP2J2
56

CYP1A2
1054

CYP2A6
543

CYP2B6
664

CYP2E1
667

P-gp
1537

BCRP
561

OAT1
326

OAT3
339

OATP1B1
406

OATP1B3
350

OCT2
355
CYP1A2
701

CYP2C19
293

CYP3A5
76

UGT1A6
34
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no
CYP1A2
1692
 no
CYP2A6
739
 no
CYP2C19
1553
 no
CYP2C19
1553
 no
CYP2C8
965
 no
CYP2C9
1819
 no
CYP2C9
1819
 no
CYP2D6
1891
 no
CYP2E1
970
 no
CYP3A4
1925
 no
CYP3A4
1925
 no
CYP3A5
130
 no
CYP3A5
130
 no
UGT1A6
141
 no
BCRP
773
 not significant
OAT1
603
 not significant
OAT3
644
 not significant
OATP1B1
803
 not significant
OATP1B3
715
 not significant
OCT2
648
 not significant
P-gp
1650
 weak [IC50 423 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1054
 low
CYP2A6
543
 low
CYP2B6
664
 low
CYP2C9
1037
 low
CYP2E1
667
 low
CYP3A4
1737
 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
991
 minor
CYP2C8
693
 minor
CYP2D6
1217
 minor
CYP2J2
56
 minor
BCRP
561
 no
OAT1
326
 no
OAT3
339
 no
OATP1B1
406
 no
OATP1B3
350
 no
OCT2
355
 no
P-gp
1537
 weak
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0004BY
1PlusChem LLC
1P0020LY
A2B Chem
AA04814
AA Blocks
AA0003SI
ABI Chem
AC1OCEN8
AChemBlock
L14973
AK Scientific
G420
AK Scientific
J10386
AbovChem LLC
HY-B0168B
Achemtek
0102-013376
http://www.achemtek.com/96847-55-1
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
Fluorochem
506367
Hairui
HR101536
Hairui
HR143593
Hangzhou APIChem Technology
AC-1532
KeyOrganics
AS-12868
Lab Network
LN01300009
Lan Pharmatech
LQT-A00044
MedChem Express
HY-B0168B
MolPort
MolPort-006-666-270
MolPort
MolPort-019-939-251
MolPort
MolPort-042-676-060
Molcore
MC106953
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
SynQuest
1040335
SynQuest
80573
Synblock Inc
SB17447
http://www.synblock.com/product/96847-54-0.html
THE BioTek
bt-272644
https://www.thebiotek.com/product/inhibitors/bt-272644
TargetMol
T1189
TargetMol
T2594
Tetrahedron
TS34485
Toronto Research Chemicals
KIT0185
Toronto Research Chemicals
M344595
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.
PH-5139AP
ZINC
ZINC000000000506
http://zinc15.docking.org/substances/ZINC000000000506
eMolecules
300422252
eMolecules
300424416
eMolecules
31706396
eMolecules
44838574
eMolecules
89941005
eNovation Chemicals
D546565
http://www.enovationchem.com/productDetails.asp?productID=D546565
mcule
MCULE-1343334533
mcule
MCULE-1701139308
mcule
MCULE-3183239121
mcule
MCULE-7769814944
mcule
MCULE-9803369943
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

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
Name Type Language
LEVOMILNACIPRAN HYDROCHLORIDE
ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
LEVOMILNACIPRAN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
F-2695 HYDROCHLORIDE
Code English
FETZIMA
Brand Name 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 Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL99946
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
NCI_THESAURUS
C166646
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
EVMPD
SUB130559
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
DRUG BANK
DBSALT000107
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
DAILYMED
371U2ZK31U
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID801026201
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
PUBCHEM
6917778
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
SMS_ID
100000156651
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
CAS
175131-60-9
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
USAN
YY-41
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
FDA UNII
371U2ZK31U
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of LEVOMILNACIPRAN
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
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