Levomilnacipran

Identification

Summary

Levomilnacipran is a selective serotonin and norepinephrine reuptake inhibitor (SNRI) used to treat major depressive disorder (MDD) in adults.

Brand Names
Fetzima
Generic Name
Levomilnacipran
DrugBank Accession Number
DB08918
Background

Levomilnacipran is a selective serotonin and norepinephrine reuptake inhibitor (SNRI), although it is a more potent inhibitor of norepinephrine reuptake than serotonin reuptake.2,3 Levomilnacipran is the more active 1S,2R-enantiomer in the racemate milnacipran.2,6 Once administered, interconversion between levomilnacipran and its stereoisomer does not occur in humans.4 First approved by the FDA on July 25, 2013, levomilnacipran is used to treat major depressive disorder in adults.6 While levomilnacipran was previously investigated and proposed as a potential treatment for stroke in Europe, the EMA decided against this use.7

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 246.348
Monoisotopic: 246.173213336
Chemical Formula
C15H22N2O
Synonyms
  • (1S,2R)-milnacipran
  • CYCLOPROPANECARBOXAMIDE, 2-(AMINOMETHYL)-N,N-DIETHYL-1-PHENYL-, (1S,2R)-
  • Levomilnacipran
  • MILNACIPRAN, (1S,2R)-
External IDs
  • F 2695
  • F-2695
  • F2695

Pharmacology

Indication

Levomilnacipran is a serotonin and norepinephrine reuptake inhibitor indicated for the treatment of major depressive disorder (MDD) in adults.4

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofMajor depressive disorder•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Levomilnacipran is an antidepressant that binds with high affinity to human serotonin (5-HT) and norepinephrine (NE) transporters (Ki = 11 and 91 nM, respectively). It potently inhibits 5-HT and NE reuptake (IC50 = 16 - 19 and 11 nM, respectively).4 Levomilnacipran does not bind to any other receptors, ion channels, or transporters, including serotonergic (5HT1-7), α- and β adrenergic, muscarinic, or histaminergic receptors and Ca2+, Na+, K+ or Cl- channels to a significant degree.1,3,4 Levomilnacipran did not inhibit monoamine oxidase (MAO). Furthermore, levomilnacipran does not prolong the QTc interval to a clinically relevant extent.4

Mechanism of action

Levomilnacipran is a potent and selective selective serotonin and norepinephrine reuptake inhibitor (SNRI). The exact mechanism of the antidepressant action of levomilnacipran is unknown but is thought to be related to the potentiation of serotonin and norepinephrine in the central nervous system through inhibition of reuptake at serotonin and norepinephrine transporters.4 Like milnacipran, levomilnacipran is a more potent inhibitor of the norepinephrine transporter than the serotonin transporter:3 it exhibits over a 15-fold higher selectivity for norepinephrine versus serotonin reuptake inhibition.1

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
ASodium-dependent noradrenaline transporter
inhibitor
Humans
Absorption

The steady-state concentration of levomilnacipran was dose-proportional when administered at a dose ranging from 25 mg to 300 mg (2.5 times the maximum recommended dosage of levomilnacipran) once daily. After daily dosing of 120 mg levomilnacipran, the mean Cmax value was 341 ng/mL, and the mean steady-state AUC value was 5196 ng x h/mL.4

The relative bioavailability of oral levomilnacipran extended-release capsules was 92% when compared to oral solution. The median time to peak concentration (Tmax) of levomilnacipran ranges from six to eight hours after oral administration. Levomilnacipran concentration was not significantly affected when it was administered with food.4

Volume of distribution

Levomilnacipran is widely distributed, with an apparent volume of distribution ranging from 387 to 473 L.4

Protein binding

Levomilnacipran is 22% bound to plasma proteins over the concentration range of 10 to 1000 ng/mL.4

Metabolism

Levomilnacipran undergoes desethylation to form desethyl levomilnacipran (or N-desethyl levomilnacipran) and hydroxylation to form p-hydroxy-levomilnacipran, which are pharmacologically inactive. Both oxidative metabolites can undergo further glucuronidation. Desethylation is primarily catalyzed by CYP3A4 with minor contributions by CYP2C8, 2C19, 2D6, and 2J2.3,4

Hover over products below to view reaction partners

Route of elimination

Levomilnacipran and its metabolites are eliminated primarily by renal excretion. Following oral administration of 14C-levomilnacipran solution, approximately 58% of the dose is excreted in urine as unchanged levomilnacipran. N-desethyl levomilnacipran was the major metabolite excreted in the urine, accounting for approximately 18% of the dose. Other identifiable metabolites excreted in the urine were levomilnacipran glucuronide (4%), desethyl levomilnacipran glucuronide (3%), p-hydroxy levomilnacipran glucuronide (1%), and p-hydroxy levomilnacipran (1%).4

Half-life

The apparent terminal elimination half-life of extended-release levomilnacipran is approximately 12 hours.4

Clearance

Following oral administration, the mean apparent total clearance of levomilnacipran is 21-29 L/h.4

Adverse Effects
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Toxicity

The oral LD50 in rats was 238 mg/kg.5

There is limited clinical experience with levomilnacipran overdose in humans. In clinical studies, cases of ingestions up to 360 mg daily were reported with none being fatal. As there is no known specific antidote, levomilnacipran overdose should be managed with supportive measures, including close medical supervision and monitoring, with the consideration of possible multiple drug involvement. The high volume of distribution of levomilnacipran suggests that dialysis will not be effective in reducing levomilnacipran plasma concentrations.4

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Levomilnacipran which could result in a higher serum level.
AbametapirThe serum concentration of Levomilnacipran can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Levomilnacipran.
AcarboseThe risk or severity of hypoglycemia can be increased when Levomilnacipran is combined with Acarbose.
AceclofenacLevomilnacipran may increase the antiplatelet activities of Aceclofenac.
Food Interactions
  • Avoid alcohol. Ingesting alcohol may compromise the extended-release dosage form of levomilnacipran, causing an accelerated release of the drug and increasing its serum concentration.
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Taking herbs with antiplatelet or anticoagulant activity may increase the risk of bleeding.
  • Exercise caution with grapefruit products. Grapefruit is a moderate to strong CYP3A4 inhibitor. Do not exceed a maximum levomilnacipran dose of 80mg daily when taking strong CYP3A4 inhibitors.
  • Exercise caution with St. John's Wort. Administering levomilnacipran with St. John's Wort may increase the risk of serotonin syndrome.
  • Take with or without food. Food does not affect drug absorption and exposure to a clinically significant extent.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Levomilnacipran hydrochloride371U2ZK31U175131-60-9XNCDYJFPRPDERF-NQQJLSKUSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FetzimaCapsule, extended release80 mgOralAbbvie2016-04-22Not applicableCanada flag
FetzimaCapsule, extended release40 mg/1OralAvera McKennan Hospital2015-03-092017-05-24US flag
FetzimaCapsule, extended release40 mg/1OralAllergan, Inc.2013-07-25Not applicableUS flag
FetzimaCapsule, extended release40 mgOralAbbvie2015-11-19Not applicableCanada flag
FetzimaCapsule, extended release120 mg/1OralAllergan, Inc.2013-07-25Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LevomilnacipranCapsule, extended release40 mg/1OralAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
LevomilnacipranCapsule, extended release120 mg/1OralAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
LevomilnacipranCapsule, extended release20 mg/1OralAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
LevomilnacipranCapsule, extended release80 mg/1OralAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FetzimaLevomilnacipran hydrochloride (20 mg/1) + Levomilnacipran hydrochloride (40 mg/1)KitOralAllergan, Inc.2013-07-25Not applicableUS flag
FetzimaLevomilnacipran hydrochloride (20 mg/1) + Levomilnacipran hydrochloride (40 mg/1)KitOralAllergan, Inc.2023-03-24Not applicableUS flag
FetzimaLevomilnacipran hydrochloride (20 mg/1) + Levomilnacipran hydrochloride (40 mg/1)KitOralAllergan, Inc.2013-07-25Not applicableUS flag
FetzimaLevomilnacipran hydrochloride (20 mg/1) + Levomilnacipran hydrochloride (40 mg/1)KitOralAllergan, Inc.2023-03-24Not applicableUS flag

Categories

ATC Codes
N06AX28 — Levomilnacipran
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylacetamides
Direct Parent
Phenylacetamides
Alternative Parents
Aralkylamines / Cyclopropanecarboxylic acids and derivatives / Tertiary carboxylic acid amides / Amino acids and derivatives / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Amine / Amino acid or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclopropanecarboxylic acid or derivatives / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
UGM0326TXX
CAS number
96847-54-0
InChI Key
GJJFMKBJSRMPLA-DZGCQCFKSA-N
InChI
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
IUPAC Name
(1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide
SMILES
CCN(CC)C(=O)[C@]1(C[C@H]1CN)C1=CC=CC=C1

References

General References
  1. Asnis GM, Henderson MA: Levomilnacipran for the treatment of major depressive disorder: a review. Neuropsychiatr Dis Treat. 2015 Jan 9;11:125-35. doi: 10.2147/NDT.S54710. eCollection 2015. [Article]
  2. Mago R, Mahajan R, Thase ME: Levomilnacipran: a newly approved drug for treatment of major depressive disorder. Expert Rev Clin Pharmacol. 2014 Mar;7(2):137-45. doi: 10.1586/17512433.2014.889563. [Article]
  3. Bruno A, Morabito P, Spina E, Muscatello MR: The Role of Levomilnacipran in the Management of Major Depressive Disorder: A Comprehensive Review. Curr Neuropharmacol. 2016;14(2):191-9. [Article]
  4. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]
  5. Allergan: FETZIMA (Levomilnacipran) MSDS [Link]
  6. FDA Drug Approval Package: FETZIMA (levomilnacipran) Extended-Release Capsules [Link]
  7. European Medicines Agency decision: P/0128/2015 [Link]
KEGG Drug
D10072
PubChem Compound
6917779
PubChem Substance
175427154
ChemSpider
5293005
BindingDB
50032379
RxNav
1433212
ChEBI
136040
ChEMBL
CHEMBL99946
ZINC
ZINC000000000506
Wikipedia
Levomilnacipran

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceNone (i.e. Healthy Volunteers)1
4CompletedTreatmentMajor Depressive Disorder (MDD)3
3CompletedTreatmentDepression / Major Depressive Disorder (MDD)1
3CompletedTreatmentIschemic Stroke1
3CompletedTreatmentMajor Depressive Disorder (MDD)8

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral20.000 mg
Capsule, extended releaseOral120 mg
Capsule, extended releaseOral20 mg
Capsule, extended releaseOral40 mg
Capsule, extended releaseOral80 mg
KitOral
Capsule, extended releaseOral120 mg/1
Capsule, extended releaseOral20 mg/1
Capsule, extended releaseOral40 mg/1
Capsule, extended releaseOral80 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
USRE43879No2012-12-252023-06-03US flag
US8481598No2013-07-092031-03-02US flag
US8865937No2014-10-212032-05-23US flag

Properties

State
Solid
Experimental Properties
Not Available
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
Polarizability28.34 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9889
Caco-2 permeable+0.5914
P-glycoprotein substrateSubstrate0.5928
P-glycoprotein inhibitor INon-inhibitor0.902
P-glycoprotein inhibitor IINon-inhibitor0.8787
Renal organic cation transporterNon-inhibitor0.8119
CYP450 2C9 substrateNon-substrate0.8494
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6514
CYP450 1A2 substrateNon-inhibitor0.6383
CYP450 2C9 inhibitorNon-inhibitor0.7697
CYP450 2D6 inhibitorNon-inhibitor0.7718
CYP450 2C19 inhibitorNon-inhibitor0.8587
CYP450 3A4 inhibitorNon-inhibitor0.6327
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7004
Ames testNon AMES toxic0.8013
CarcinogenicityNon-carcinogens0.5456
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.6162 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.993
hERG inhibition (predictor II)Non-inhibitor0.6823
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-5910000000-6041b8fa3fe52b885b2c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0690000000-e358699dd4ba3ced536b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-3970000000-6a00667afb142f57e896
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-3390000000-4a22ea8684355b17c232
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-9360000000-32dc0f23bf29a8d2ba83
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00fr-9300000000-77df58f97fce227ecf77
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9700000000-217adea06b61e02741c0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.74638
predicted
DeepCCS 1.0 (2019)
[M+H]+160.10439
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.19753
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Levomilnacipran inhibits the human serotonin transporter with an inhibitory constant (Ki) of 11 nM.
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Levomilnacipran inhibits the human norepinephrine transporter with an inhibitory constant (Ki) of 91 nM.
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Bruno A, Morabito P, Spina E, Muscatello MR: The Role of Levomilnacipran in the Management of Major Depressive Disorder: A Comprehensive Review. Curr Neuropharmacol. 2016;14(2):191-9. [Article]
  2. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Bruno A, Morabito P, Spina E, Muscatello MR: The Role of Levomilnacipran in the Management of Major Depressive Disorder: A Comprehensive Review. Curr Neuropharmacol. 2016;14(2):191-9. [Article]
  2. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Bruno A, Morabito P, Spina E, Muscatello MR: The Role of Levomilnacipran in the Management of Major Depressive Disorder: A Comprehensive Review. Curr Neuropharmacol. 2016;14(2):191-9. [Article]
  2. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
Gene Name
CYP2J2
Uniprot ID
P51589
Uniprot Name
Cytochrome P450 2J2
Molecular Weight
57610.165 Da
References
  1. Bruno A, Morabito P, Spina E, Muscatello MR: The Role of Levomilnacipran in the Management of Major Depressive Disorder: A Comprehensive Review. Curr Neuropharmacol. 2016;14(2):191-9. [Article]
  2. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA Approved Drug Products: FETZIMA (levomilnacipran) extended-release capsules, for oral use (August 2023) [Link]

Drug created at August 01, 2013 20:17 / Updated at January 02, 2024 23:49