levomilnacipran 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
40 mg O

ADMET properties:

PropertyValueReference
fu (Fraction unbound in plasma) 0.68 % Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K
BA (Bioavailability) 0.88 % Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT1,AKT2,AKT3,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK3,MAP3K7,MAPK12,MAPK7,MET,NTRK2,PDK2,PDK4,PIM2,PRKDC,SIK2,SIK3,TEK,TGFBR1 33
kinase-selectivity-class PDK4 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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
Blepharospasm 511.79 45.66 257 22107 55188 90550895
Taste disorder 458.26 45.66 247 22117 61299 90544784
Epilepsy 357.08 45.66 233 22131 81973 90524110
Infusion site reaction 310.03 45.66 131 22233 18908 90587175
Gastrooesophageal reflux disease 307.71 45.66 284 22080 166053 90440030
Back injury 247.12 45.66 150 22214 46472 90559611
Memory impairment 215.28 45.66 254 22110 196990 90409093
Onychomadesis 201.09 45.66 131 22233 45867 90560216
Breast cancer stage III 193.57 45.66 163 22201 84284 90521799
Peripheral venous disease 192.40 45.66 162 22202 83759 90522324
Product quality issue 187.79 45.66 156 22208 79169 90526914
Paraesthesia 173.45 45.66 258 22106 250068 90356015
Overlap syndrome 170.38 45.66 68 22296 8480 90597603
Facet joint syndrome 155.15 45.66 154 22210 98235 90507848
Live birth 145.88 45.66 135 22229 78972 90527111
Hypercholesterolaemia 141.04 45.66 148 22216 100744 90505339
Nail disorder 127.10 45.66 110 22254 58957 90547126
Neck pain 124.56 45.66 147 22217 113816 90492267
Hypoaesthesia 120.88 45.66 250 22114 313960 90292123
Night sweats 118.01 45.66 152 22212 128614 90477469
Abdominal pain upper 117.93 45.66 256 22108 332418 90273665
Liver function test increased 117.73 45.66 124 22240 84731 90521352
Wound infection 117.53 45.66 138 22226 106264 90499819
Migraine 117.35 45.66 186 22178 190206 90415877
Bursitis 116.90 45.66 153 22211 131501 90474582
Joint range of motion decreased 113.31 45.66 153 22211 135490 90470593
Lip dry 108.29 45.66 129 22235 100826 90505257
Gait inability 104.23 45.66 153 22211 146303 90459780
Dry mouth 100.14 45.66 170 22194 183889 90422194
Lung disorder 94.49 45.66 148 22216 149735 90456348
Obesity 91.13 45.66 121 22243 105386 90500697
Fatigue 90.81 45.66 91 22273 1153932 89452151
C-reactive protein increased 86.33 45.66 158 22206 181231 90424852
Exostosis 83.38 45.66 83 22281 53051 90553032
Breast cancer stage II 82.53 45.66 69 22295 35265 90570818
Rheumatic fever 81.38 45.66 140 22224 152981 90453102
Inflammation 80.52 45.66 152 22212 178440 90427643
Irritable bowel syndrome 78.42 45.66 164 22200 207284 90398799
Sleep disorder 77.73 45.66 159 22205 197871 90408212
Musculoskeletal pain 73.81 45.66 143 22221 171108 90434975
Cough 68.89 45.66 6 22358 368956 90237127
Hypotension 67.57 45.66 3 22361 325394 90280689
Folliculitis 66.37 45.66 152 22212 204201 90401882
Maternal exposure during pregnancy 63.31 45.66 214 22150 359849 90246234
Urinary tract infection 62.86 45.66 3 22361 305629 90300454
Psoriatic arthropathy 62.53 45.66 159 22205 228176 90377907
Blood cholesterol increased 62.40 45.66 150 22214 207862 90398221
Drug tolerance 61.56 45.66 44 22320 17872 90588211
Muscle injury 60.25 45.66 134 22230 176520 90429563
Dyspnoea 59.88 45.66 78 22286 880877 89725206
Osteoarthritis 59.63 45.66 142 22222 195588 90410495
Therapeutic product effect incomplete 59.43 45.66 141 22223 193755 90412328
Dislocation of vertebra 57.49 45.66 70 22294 55898 90550185
Back pain 56.98 45.66 6 22358 317169 90288914
Red blood cell sedimentation rate increased 56.86 45.66 85 22279 82510 90523573
Hypocholesterolaemia 56.79 45.66 29 22335 6420 90599663
Muscular weakness 56.67 45.66 144 22220 206522 90399561
Duodenal ulcer perforation 56.38 45.66 150 22214 221138 90384945
Fibromyalgia 55.81 45.66 143 22221 206126 90399957
Drug intolerance 54.76 45.66 237 22127 447354 90158729
Muscle spasms 54.61 45.66 161 22203 251722 90354361
Impaired healing 53.95 45.66 153 22211 234046 90372037
Blister 53.40 45.66 161 22203 254837 90351246
Type 2 diabetes mellitus 53.03 45.66 139 22225 203105 90402978
Persistent genital arousal disorder 52.14 45.66 15 22349 685 90605398
Laryngitis 51.36 45.66 63 22301 50690 90555393
Bone erosion 50.74 45.66 64 22300 52957 90553126
Stomatitis 50.68 45.66 166 22198 274532 90331551
Fall 50.59 45.66 28 22336 481782 90124301
Toxicity to various agents 50.30 45.66 6 22358 287840 90318243
Product use in unapproved indication 49.82 45.66 189 22175 336047 90270036
Ear pain 49.52 45.66 66 22298 57636 90548447
Injury 49.48 45.66 133 22231 197216 90408867
Product dose omission issue 48.76 45.66 7 22357 291680 90314403
Depression 47.05 45.66 172 22192 300429 90305654

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
Dissociation 140.04 57.16 24 278 3774 42617259

FDA Adverse Event Reporting System (Geriatric)

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
Blepharospasm 482.55 60.07 222 19453 54629 110514995
Taste disorder 407.32 60.07 209 19466 65178 110504446
Epilepsy 290.11 60.07 195 19480 100014 110469610
Infusion site reaction 287.99 60.07 111 19564 17571 110552053
Gastrooesophageal reflux disease 284.69 60.07 244 19431 179732 110389892
Back injury 262.21 60.07 140 19535 47259 110522365
Onychomadesis 230.65 60.07 127 19548 45536 110524088
Memory impairment 216.41 60.07 218 19457 196726 110372898
Breast cancer stage III 198.39 60.07 141 19534 78976 110490648
Peripheral venous disease 195.15 60.07 143 19532 83974 110485650
Overlap syndrome 191.95 60.07 69 19606 8990 110560634
Hypercholesterolaemia 187.54 60.07 144 19531 90693 110478931
Product quality issue 185.19 60.07 134 19541 77165 110492459
Paraesthesia 171.66 60.07 228 19447 276293 110293331
Live birth 156.36 60.07 116 19559 69368 110500256
Facet joint syndrome 152.32 60.07 131 19544 96697 110472927
Nail disorder 151.58 60.07 106 19569 57829 110511795
Neck pain 145.68 60.07 142 19533 122988 110446636
Wound infection 144.66 60.07 127 19548 96338 110473286
Night sweats 144.65 60.07 147 19528 133836 110435788
Maternal exposure during pregnancy 142.76 60.07 200 19475 254683 110314941
Liver function test increased 133.61 60.07 117 19558 88431 110481193
Joint range of motion decreased 130.28 60.07 133 19542 121699 110447925
Abdominal pain upper 123.54 60.07 222 19453 348889 110220735
Migraine 121.25 60.07 151 19524 171501 110398123
Bursitis 119.67 60.07 131 19544 129787 110439837
Hypoaesthesia 119.15 60.07 206 19469 314017 110255607
Rheumatic fever 118.85 60.07 127 19548 122452 110447172
Irritable bowel syndrome 115.25 60.07 144 19531 164071 110405553
Gait inability 112.77 60.07 130 19545 136246 110433378
Obesity 110.88 60.07 118 19557 113233 110456391
Folliculitis 106.61 60.07 140 19535 167513 110402111
Lip dry 106.51 60.07 109 19566 99974 110469650
Impaired healing 102.18 60.07 149 19526 196568 110373056
Muscle injury 101.23 60.07 125 19550 140682 110428942
Dry mouth 97.46 60.07 147 19528 199801 110369823
Lung disorder 97.34 60.07 139 19536 179908 110389716
Osteoarthritis 95.82 60.07 139 19536 182484 110387140
Musculoskeletal pain 95.59 60.07 139 19536 182884 110386740
Sleep disorder 95.34 60.07 145 19530 198499 110371125
Glossodynia 91.31 60.07 151 19524 221853 110347771
Psoriatic arthropathy 89.35 60.07 140 19535 196621 110373003
Helicobacter infection 89.03 60.07 134 19541 181743 110387881
Anti-cyclic citrullinated peptide antibody positive 88.97 60.07 134 19541 181850 110387774
Inflammation 82.93 60.07 134 19541 193104 110376520
Type 2 diabetes mellitus 81.70 60.07 127 19548 177105 110392519
Duodenal ulcer perforation 81.45 60.07 127 19548 177573 110392051
Hypotension 80.10 60.07 3 19672 523846 110045778
Synovitis 79.19 60.07 160 19515 273932 110295692
Blood cholesterol increased 79.10 60.07 128 19547 184657 110384967
Fibromyalgia 76.73 60.07 121 19554 170788 110398836
Pericarditis 74.42 60.07 137 19538 218977 110350647
C-reactive protein increased 73.69 60.07 136 19539 217783 110351841
Blister 73.27 60.07 139 19536 227237 110342387
Stomatitis 72.47 60.07 153 19522 270089 110299535
Drug intolerance 71.12 60.07 195 19480 406317 110163307
Fatigue 67.90 60.07 70 19605 1215888 109353736
Dyspnoea 67.30 60.07 59 19616 1106813 109462811
Muscular weakness 66.99 60.07 141 19534 248327 110321297
Hand deformity 66.02 60.07 130 19545 218376 110351248
Hypocholesterolaemia 65.95 60.07 29 19646 6392 110563232
Exostosis 65.85 60.07 59 19616 45897 110523727
Breast cancer stage II 64.46 60.07 47 19628 27328 110542296
Injury 64.20 60.07 114 19561 177151 110392473
Muscle spasms 63.87 60.07 148 19527 278009 110291615
Toxicity to various agents 63.72 60.07 6 19669 480549 110089075
Wound 63.15 60.07 133 19542 234304 110335320
Lupus vulgaris 61.86 60.07 50 19625 33833 110535791
Dislocation of vertebra 60.41 60.07 55 19620 43666 110525958

FDA Adverse Event Reporting System (Pediatric)

None

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 D000068760 Serotonin and Noradrenaline Reuptake Inhibitors
MeSH PA D000928 Antidepressive Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D049990 Membrane Transport Modulators
FDA EPC N0000175749 Serotonin and Norepinephrine Reuptake Inhibitor
CHEBI has role CHEBI:35469 antidepressant

Related Drugs by ATC class:

N06AX Other antidepressants 28 drugs
agomelatinebifemelanebrexanolonebupropiondesvenlafaxinedextromethorphanduloxetineesketaminegepironemedifoxaminemianserinmilnacipran show all 28 →

Drug Use | Suggest Off label Use Form| |View source of the data|

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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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 ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 20MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 40MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 80MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL RE43879 Jan. 11, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 120MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL 8481598 March 2, 2031 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 20MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL 8481598 March 2, 2031 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 40MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL 8481598 March 2, 2031 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
EQ 80MG BASE FETZIMA ABBVIE 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 ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL March 24, 2026 INFORMATION ADDED TO SECTION 8.4 OF THE LABELING TO DESCRIBE THE RESULTS FROM STUDY LVM-MD-11 AND LVM-MD-14
EQ 20MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL March 24, 2026 INFORMATION ADDED TO SECTION 8.4 OF THE LABELING TO DESCRIBE THE RESULTS FROM STUDY LVM-MD-11 AND LVM-MD-14
EQ 40MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL March 24, 2026 INFORMATION ADDED TO SECTION 8.4 OF THE LABELING TO DESCRIBE THE RESULTS FROM STUDY LVM-MD-11 AND LVM-MD-14
EQ 80MG BASE FETZIMA ABBVIE N204168 July 25, 2013 RX CAPSULE, EXTENDED RELEASE ORAL March 24, 2026 INFORMATION ADDED TO SECTION 8.4 OF THE LABELING TO DESCRIBE THE RESULTS FROM STUDY LVM-MD-11 AND LVM-MD-14

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
4032886 VANDF
CHEBI:136040 CHEBI
CHEMBL99946 ChEMBL_ID
CHEMBL2105732 ChEMBL_ID
7435 IUPHAR_LIGAND_ID
175131-60-9 SECONDARY_CAS_RN
DB08918 DRUGBANK_ID
1433211 RXNORM
204684 MMSL
29577 MMSL
31358 MMSL
d08114 MMSL
015223 NDDF
015224 NDDF
29670611000001104 SNOMEDCT_US
61851000087102 SNOMEDCT_US
C3541367 UMLSCUI
D000078862 MESH_DESCRIPTOR_UI
8740 INN_ID
6917779 PUBCHEM_CID
UGM0326TXX UNII
UGM0326TXX INXIGHT DRUGS

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