levomilnacipran Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
4864 96847-54-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • levomilnacipran
  • levomilnacipran hydrochloride
  • fetzima
  • levomilnacipran HCl
a selective serotonin and norepinephrine reuptake inhibitor (SNRI), 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
  • Molecular weight: 246.35
  • Formula: C15H22N2O
  • CLOGP: 1.91
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 46.33
  • ALOGS: -2.30
  • ROTB: 5

  • Status: ONP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
40 mg O

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
July 25, 2013 FDA FOREST LABS INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Persistent genital arousal disorder 101.67 33.25 15 1044 304 53347703
Suicidal ideation 71.40 33.25 31 1028 60480 53287527
Blepharospasm 58.35 33.25 13 1046 2723 53345284
Serotonin syndrome 49.90 33.25 19 1040 26387 53321620
Taste disorder 44.55 33.25 13 1046 7955 53340052
Memory impairment 33.87 33.25 21 1038 84736 53263271

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC N06AX28 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Other antidepressants
FDA MoA N0000000102 Norepinephrine Uptake Inhibitors
FDA MoA N0000000109 Serotonin Uptake Inhibitors
MeSH PA D000928 Antidepressive Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D000068760 Serotonin and Noradrenaline Reuptake Inhibitors
FDA EPC N0000175749 Serotonin and Norepinephrine Reuptake Inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Major depressive disorder indication 370143000
Angle-closure glaucoma contraindication 392291006 DOID:13550

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.64 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 120MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 20MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 40MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 80MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 120MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL 8481598 March 2, 2031 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 20MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL 8481598 March 2, 2031 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 40MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL 8481598 March 2, 2031 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 80MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL 8481598 March 2, 2031 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 120MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL Oct. 7, 2022 INFORMATION ADDED TO THE LABELING TO DESCRIBE STUDY LVM-MD-15 TO FULFILL POSTMARKETING COMMITMENT 1943-4
EQ 20MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL Oct. 7, 2022 INFORMATION ADDED TO THE LABELING TO DESCRIBE STUDY LVM-MD-15 TO FULFILL POSTMARKETING COMMITMENT 1943-4
EQ 40MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL Oct. 7, 2022 INFORMATION ADDED TO THE LABELING TO DESCRIBE STUDY LVM-MD-15 TO FULFILL POSTMARKETING COMMITMENT 1943-4
EQ 80MG BASE FETZIMA ALLERGAN N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL Oct. 7, 2022 INFORMATION ADDED TO THE LABELING TO DESCRIBE STUDY LVM-MD-15 TO FULFILL POSTMARKETING COMMITMENT 1943-4

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent serotonin transporter Transporter INHIBITOR Ki 7.95 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Ki 7.04 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Sodium-dependent dopamine transporter Transporter IC50 5.49 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 8.07 CHEMBL
Glutamate NMDA receptor Ion channel IC50 5.20 CHEMBL

External reference:

IDSource
D10072 KEGG_DRUG
4032886 VUID
N0000189503 NUI
175131-60-9 SECONDARY_CAS_RN
4032886 VANDF
CHEBI:136040 CHEBI
CHEMBL99946 ChEMBL_ID
CHEMBL2105732 ChEMBL_ID
7435 IUPHAR_LIGAND_ID
8740 INN_ID
DB08918 DRUGBANK_ID
UGM0326TXX UNII
65833 PUBCHEM_CID
1433211 RXNORM
204684 MMSL
29577 MMSL
31358 MMSL
d08114 MMSL
015223 NDDF
015224 NDDF
D000078862 MESH_DESCRIPTOR_UI
C3541367 UMLSCUI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fetzima HUMAN PRESCRIPTION DRUG LABEL 1 0456-2212 CAPSULE, EXTENDED RELEASE 120 mg ORAL NDA 35 sections
Fetzima HUMAN PRESCRIPTION DRUG LABEL 1 0456-2220 CAPSULE, EXTENDED RELEASE 20 mg ORAL NDA 35 sections
Fetzima HUMAN PRESCRIPTION DRUG LABEL 1 0456-2240 CAPSULE, EXTENDED RELEASE 40 mg ORAL NDA 35 sections
Fetzima HUMAN PRESCRIPTION DRUG LABEL 1 0456-2280 CAPSULE, EXTENDED RELEASE 80 mg ORAL NDA 35 sections
Levomilnacipran HUMAN PRESCRIPTION DRUG LABEL 1 65162-411 CAPSULE, EXTENDED RELEASE 20 mg ORAL ANDA 29 sections
Levomilnacipran HUMAN PRESCRIPTION DRUG LABEL 1 65162-437 CAPSULE, EXTENDED RELEASE 80 mg ORAL ANDA 29 sections
Levomilnacipran HUMAN PRESCRIPTION DRUG LABEL 1 65162-455 CAPSULE, EXTENDED RELEASE 120 mg ORAL ANDA 29 sections
Levomilnacipran HUMAN PRESCRIPTION DRUG LABEL 1 65162-960 CAPSULE, EXTENDED RELEASE 40 mg ORAL ANDA 29 sections