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

Details

Stereochemistry RACEMIC
Molecular Formula C15H22N2O
Molecular Weight 246.348
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MILNACIPRAN

SMILES

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

InChI

InChIKey=GJJFMKBJSRMPLA-HIFRSBDPSA-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+/m1/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

Description
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022256s013lbl.pdf

Milnacipran is the only marketed serotonin/norepinephrine (5-HT/NE) reuptake inhibitor (SNRI) reported to have greater relative potency at NET than SERT in vitro and is the first SNRI to report equal occupancy of both transporters at clinical doses. Milnacipran is a racemic mixture of the 1S, 2R (F2695/levomilnacipran) and 1R, 2S (F2696/dextromilnacipran) enantiomers. Savella® (Milnacipran) is indicated for the management of fibromyalgia.

CNS Activity

Originator

Fabre, P.
12
Curator's Comment: Milnacipran was synthesised as a racemic mixture at the PIERRE FABRE MEDICAMENT Research Centre (Castres, France).

Approval Year

2009
334
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 290.0 nM [Ki]
Inhibitor
8228
 16.9 nM [Ki]
Inhibitor
8228
 139.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
SAVELLA

Approved Use

Savella is indicated for the management of fibromyalgia. Savella is not approved for use in pediatric patients [see Use in Specific Populations (8.4)

Launch Date

1.2318912E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
132 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26663198/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
150 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8923123/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1316.9 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26663198/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26663198/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8923123/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
6 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022256s023lbl.pdf
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
87%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8923123/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
87%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022256s023lbl.pdf
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILNACIPRAN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
unhealthy, 48.6
n = 181
Health Status: unhealthy
Condition: Fibromyalgia
Age Group: 48.6
Sex: M+F
Population Size: 181
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
Disc. AE: Nausea, Blood pressure increased...
AEs leading to
discontinuation/dose reduction:
Nausea (2.4%)
Blood pressure increased (1.4%)
Heart rate increased (1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Disc. AE: Suicidal ideation, Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Serotonin syndrome
Neuroleptic malignant syndrome
Blood pressure increased
Heart rate increased
Seizures
Hepatotoxicity
ALT increased (mild)
Aspartate aminotransferase increase (mild)
Hepatitis fulminant (rare)
Bleeding
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Disc. AE: Nausea, Palpitations...
AEs leading to
discontinuation/dose reduction:
Nausea (6%)
Palpitations (3%)
Headache (2%)
Constipation (1%)
Heart rate increased (1%)
Hyperhidrosis (1%)
Vomiting (1%)
Dizziness (1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.5
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.5
Disc. AE: Suicidal ideation...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation (1.3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.5
AEs

AEs

AESignificanceDosePopulation
Heart rate increased 1%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
unhealthy, 48.6
n = 181
Health Status: unhealthy
Condition: Fibromyalgia
Age Group: 48.6
Sex: M+F
Population Size: 181
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
Blood pressure increased 1.4%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
unhealthy, 48.6
n = 181
Health Status: unhealthy
Condition: Fibromyalgia
Age Group: 48.6
Sex: M+F
Population Size: 181
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
Nausea 2.4%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
unhealthy, 48.6
n = 181
Health Status: unhealthy
Condition: Fibromyalgia
Age Group: 48.6
Sex: M+F
Population Size: 181
Sources:
https://pubmed.ncbi.nlm.nih.gov/24188161
Page: p.593
Bleeding Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Blood pressure increased Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Heart rate increased Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Hepatotoxicity Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Neuroleptic malignant syndrome Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Seizures Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Serotonin syndrome Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Suicidal ideation Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
ALT increased mild
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Aspartate aminotransferase increase mild
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Hepatitis fulminant rare
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.1
Constipation 1%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Dizziness 1%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Heart rate increased 1%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Hyperhidrosis 1%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Vomiting 1%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Headache 2%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Palpitations 3%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Nausea 6%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.11
Suicidal ideation 1.3%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.5
unhealthy
Health Status: unhealthy
Condition: Fibromyalgia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022256s011lbl.pdf
Page: p.5
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1579

substrate
1709
inhibitor
1752

inducer
383
inhibitor
1837

substrate
1193
inhibitor
1599

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1509

CYP2A6
704

CYP2C19
1463

CYP2E1
876
P-gp
1527

CYP2C19
985

CYP1A2
1032
CYP1A2
689

CYP2B6
538

CYP2C8
168

CYP2C19
290

CYP3A4/5
120
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1673
 no
CYP1A2
1673
 no
CYP2A6
736
 no
CYP2B6
985
 no
CYP2C19
1537
 no
CYP2C19
1537
 no
CYP2C8
955
 no
CYP2C9
1803
 no
CYP2C9
1803
 no
CYP2D6
1875
 no
CYP2E1
964
 no
CYP3A4
1909
 no
CYP3A4/5
330
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1527
 no
CYP2C19
985
 no
no (co-administration study)
Comment: no changes in PK of warfarin or milnacipran were observed
Page: 55.0
CYP1A2
1032
 no
unlikely (co-administration study)
Comment: when coadministered with carbamazepine, exposure (Cmax and AUC) to milnacipran decreased by 18% and 19%, respectively;
Page: 55.0
CYP2D6
1193
 no
unlikely (co-administration study)
Comment: At steady state, Cmax and AUC for milnacipran increased by only 10% and 20% when coadministered with levomepromazine; no changes in PK of warfarin or milnacipran were observed
Page: 55.0
CYP3A4
1709
 no
unlikely (co-administration study)
Comment: when coadministered with carbamazepine, exposure (Cmax and AUC) to milnacipran decreased by 18% and 19%, respectively;
Page: 55.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1632
Sourcing

Sourcing

Vendor/AggregatorIDURL
3B Scientific (Wuhan) Corp
3B2-6287
http://www.3bsc.com/index/pro_info.php?id=116365
AK Scientific, Inc. (AKSCI)
R211
http://www.aksci.com/item_detail.php?cat=R211
Acorn PharmaTech
ACN-035533
http://www.acornpharmatech.com/
Ambinter
Amb22801750
http://www.ambinter.com/reference/22801750
BLD Pharm
BD631023
http://www.bldpharm.com/products/92623-85-3.html
BLD Pharm
BD00756442
http://www.bldpharm.com/products/96847-55-1.html
BioCrick
BCC4194
http://www.biocrick.com/Milnacipran-BCC4194.html
CSNpharm
CSN18592
https://www.csnpharm.com/products/milnacipran.html
Chem Scene
CS-2009
http://www.chemscene.com/92623-85-3.html
ChemMol
99177637
http://www.chemmol.com/chemmol/99177637.html
ChemMol
99185159
http://www.chemmol.com/chemmol/99185159.html
Clearsynth
CS-P-00447
http://www.clearsynth.com/en/CSP00447.html
Hairui
HR143593
http://www.hairuichem.com/en/product/92623-85-3.html
Lab Network
LN01343162
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343162
MedChem Express
HY-B0168
https://www.medchemexpress.com/milnacipran.html
MuseChem
I012513
https://www.musechem.com/product/I012513.html
OChem
10310
http://www.ocheminc.com/index.php?act=psearch&pid=623M853
Sigma-Aldrich
CDS022174_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/cds022174?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S006221
http://www.smolecule.com/products/s006221
Smolecule
S535456
http://www.smolecule.com/products/s535456
THE BioTek
bt-255210
https://www.thebiotek.com/product/inhibitors/bt-255210
THE BioTek
bt-276385
https://www.thebiotek.com/product/inhibitors/bt-276385
iChemical
EBD2321826
http://www.ichemical.com/products/92623-85-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
PubMed

PubMed

TitleDatePubMed
Which bioequivalence study for a racemic drug? Application to milnacipran.
1998 Apr-Jun
High-performance liquid chromatographic method to screen and quantitate seven selective serotonin reuptake inhibitors in human serum.
2001 Sep 25
Remarkable effect of milnacipran in the treatment of Japanese major depressive patients.
2002 Jun
Clinical utility of milnacipran in comparison with other antidepressants.
2002 Jun
Pharmacology and pharmacokinetics of milnacipran.
2002 Jun
Silent thyroiditis associated with short-term lithium therapy.
2002 Nov-Dec
[Experience with ixel (milnacipran hydrochloride) use in the treatment of patients with post-stroke depression].
2003
[Pharmacokinetics and drug interaction of antidepressants and anti-manic drugs].
2003
Milnacipran and pindolol: a randomized trial of reduction of antidepressant latency.
2003 Dec
Comparison of effects of dual transporter inhibitors on monoamine transporters and extracellular levels in rats.
2003 Dec
Parkinsonism associated with a serotonin and noradrenaline reuptake inhibitor, milnacipran.
2003 Jan
Favorable effect of milnacipran on depression induced by interferon-alpha.
2003 Spring
Milnacipran treatment of a terminally ill cancer patient with major depressive disorder.
2004 Aug
Differential effects of fluvoxamine, paroxetine and milnacipran for depression, especially with regard to age.
2004 Aug
Prevalence of induced mania in patients treated with milnacipran: a comparison with paroxetine.
2004 Aug
Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity.
2004 Feb 1
Reboxetine: a norepinephrine selective reuptake pump inhibitor.
2004 Jan
A case of temporo-mandibular disorder with fibromyalgia treated with the antidepressant, milnacipran.
2004 Jul
Subjective and polysomnographic effects of milnacipran on sleep in depressed patients.
2004 Jul
Efficacy of duloxetine, a potent and balanced serotonin-norepinephrine reuptake inhibitor in persistent pain models in rats.
2004 Nov
Serotonin and noradrenaline reuptake inhibitors in animal models of pain.
2004 Oct
A double-blind placebo-controlled trial of milnacipran in the treatment of fibromyalgia.
2004 Oct
Prediction of antidepressant response to milnacipran by norepinephrine transporter gene polymorphisms.
2004 Sep
Effectiveness of milnacipran for the treatment of chronic pain: a case series.
2004 Sep-Oct
[Effects of milnacipran on neuronal excitability and synaptic transmission in neurons of the rat locus coeruleus].
2005 Jan
Anxiolytic-like effect of milnacipran in the four-plate test in mice: mechanism of action.
2005 Jul
Patents

Patents

JP2003523410A
13
JP2007505097A
24
JP2007513956A
15
JP2010070573A
3
JP2010090143A
3
JP2011510954A
142
JP4549442B2
3
USRE43879
3

Sample Use Guides

In Vivo Use Guide
Milnacipran and the L enantiomer were effective in reducing immobility in the forced swim test in rodents (EC50 ~10 mg/kg PO and ~3 mg/kg PO, respectively) compared with D enantiomer (EC50 ≥100 mg/kg PO).
Route of Administration: Oral
In Vitro Use Guide
Dextromilnacipran inhibits norepinephrine and serotonin reuptake in rat hypothalamic synaptosomes with IC50 values of 750 and 600 nM, respectively
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:02:21 UTC 2023
Edited
by admin
on Thu Jul 06 00:02:21 UTC 2023
Record UNII
G56VK1HF36
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MILNACIPRAN
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Milnacipran [WHO-DD]
Common Name English
MILNACIPRAN [MI]
Common Name English
milnacipran [INN]
Common Name English
(1RS,2SR)-2-(AMINOMETHYL)-N,N-DIETHYL-1-PHENYLCYCLOPROPANECARBOXAMIDE
Systematic Name English
MILNACIPRAN [VANDF]
Common Name English
IMPULSOR
Brand Name English
MILNACIPRAN [EMA EPAR]
Common Name English
MILNACIPRAN PIERRE FABRE MEDICAMENT
Brand Name English
CYCLOPROPANECARBOXAMIDE, 2-(AMINOMETHYL)-N,N-DIETHYL-1-PHENYL-, (1R,2S)-REL-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
WHO-VATC QN06AX17
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
EMA ASSESSMENT REPORTS IMPULSOR (REFUSED, FIBROMYALGIA)
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
NDF-RT N0000000109
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
NCI_THESAURUS C265
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
NDF-RT N0000175749
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
NDF-RT N0000000102
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
LIVERTOX NBK547960
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
EMA ASSESSMENT REPORTS MILNACIPRAN PIERRE FABRE MEDICAMENT (REFUSED: FIBROMYALGIA)
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
WHO-ATC N06AX17
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
EMA ASSESSMENT REPORTS IMPULSOR (REFUSED: FIBROMYALGIA)
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
Code System Code Type Description
MESH
C048107
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
RXCUI
588250
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
MILNACIPRAN
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
NCI_THESAURUS
C78021
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
IUPHAR
7436
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL259209
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
FDA UNII
G56VK1HF36
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
SMS_ID
100000080634
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID3048287
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
MERCK INDEX
M7545
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY Merck Index
LACTMED
Milnacipran
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
DRUG BANK
DB04896
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
INN
5701
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
DAILYMED
G56VK1HF36
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
DRUG CENTRAL
1808
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
CAS
92623-85-3
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
EVMPD
SUB08965MIG
Created by admin on Thu Jul 06 00:02:21 UTC 2023 , Edited by admin on Thu Jul 06 00:02:21 UTC 2023
PRIMARY
Related Record Type Details
Structure of MILNACIPRAN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of MILNACIPRAN
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
The plasma protein binding of milnacipran is approximately 13% and is independent of the concentration (Study# M013).
BINDING
Structure of DEXTROMILNACIPRAN
ENANTIOMER -> RACEMATE
Structure of LEVOMILNACIPRAN
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of MILNACIPRAN CARBAMOYL O-GLUCURONIDE, L-
METABOLITE -> PARENT
MAJOR
URINE
Structure of MILNACIPRAN CARBAMOYL O-GLUCURONIDE, D-
METABOLITE -> PARENT
MINOR
URINE
Structure of N-DESETHYL MILNACIPRAN
METABOLITE -> PARENT
Lower than detection limit in plasma
MAJOR
URINE
Related Record Type Details
Structure of CYCLOPROPANECARBOXYLIC ACID, 2-(AMINOMETHYL)-1-PHENYL-, CIS-
IMPURITY -> PARENT
Related Record Type Details
Structure of MILNACIPRAN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Structure of MILNACIPRAN
Absolute Bioavailability PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Structure of MILNACIPRAN
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

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