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

Stem definitionDrug idCAS RN
1230 54739-18-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fluvoxamine
  • fluvoxamine maleate
  • depromel
A selective serotonin reuptake inhibitor that is used in the treatment of DEPRESSION and a variety of ANXIETY DISORDERS. Because of its high affinity at the sigma-1 receptor, the drug was evaluated whether could prevent clinical deterioration in patients with COVID-19. At the moment, there are insufficient data to recommend either for or against use of fluvoxamine for the treatment of COVID-19.
  • Molecular weight: 318.34
  • Formula: C15H21F3N2O2
  • CLOGP: 3.03
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 56.84
  • ALOGS: -4.64
  • ROTB: 10

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.10 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 14.87 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 13.46 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 53 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 23.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 31.95 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.20 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 12.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 5, 1994 FDA

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
Drug interaction 148.42 18.86 149 5371 202945 46477597
Suicide attempt 103.17 18.86 70 5450 54966 46625576
Intentional self-injury 93.31 18.86 49 5471 24117 46656425
Intentional overdose 88.32 18.86 68 5452 64876 46615666
Toxicity to various agents 72.60 18.86 106 5414 211660 46468882
Obsessive-compulsive disorder 67.71 18.86 22 5498 3193 46677349
Serotonin syndrome 65.83 18.86 39 5481 24181 46656361
Suicidal ideation 55.57 18.86 49 5471 56333 46624209
Drug abuse 54.45 18.86 51 5469 63357 46617185
Neuroleptic malignant syndrome 52.96 18.86 26 5494 11096 46669446
Anxiety 50.92 18.86 83 5437 181874 46498668
Somnolence 43.22 18.86 71 5449 156450 46524092
Oscillopsia 41.58 18.86 8 5512 130 46680412
Schizophrenia 40.70 18.86 20 5500 8548 46671994
Completed suicide 40.02 18.86 66 5454 145854 46534688
Mydriasis 36.77 18.86 20 5500 10533 46670009
Electrocardiogram QT prolonged 36.04 18.86 37 5483 51288 46629254
Drug level increased 33.41 18.86 23 5497 18418 46662124
Torsade de pointes 31.52 18.86 19 5501 12135 46668407
Depression 30.37 18.86 64 5456 170040 46510502
Blood creatine phosphokinase increased 29.11 18.86 25 5495 27699 46652843
Tremor 28.62 18.86 50 5470 115589 46564953
Galactorrhoea 27.89 18.86 12 5508 3785 46676757
Overdose 27.75 18.86 46 5474 101933 46578609
Sopor 27.42 18.86 21 5499 19807 46660735
Mental disorder 27.24 18.86 22 5498 22403 46658139
Drug screen false positive 26.88 18.86 8 5512 869 46679673
Personality disorder 26.68 18.86 11 5509 3122 46677420
Delirium 26.42 18.86 27 5493 37201 46643341
Activation syndrome 26.26 18.86 6 5514 230 46680312
Depersonalisation/derealisation disorder 25.76 18.86 8 5512 1002 46679540
Restlessness 24.75 18.86 22 5498 25502 46655040
Alice in wonderland syndrome 23.50 18.86 4 5516 31 46680511
Dysarthria 22.71 18.86 25 5495 37473 46643069
Depressed level of consciousness 22.61 18.86 28 5492 47541 46633001
Agitation 22.24 18.86 30 5490 55385 46625157
Akinesia 21.23 18.86 8 5512 1793 46678749
Anaemia folate deficiency 20.59 18.86 5 5515 250 46680292
Congestive cardiomyopathy 20.38 18.86 11 5509 5702 46674840
Dysphoria 19.69 18.86 10 5510 4579 46675963
Aspiration of gastric residual 19.30 18.86 3 5517 12 46680530
Psychotic disorder 19.01 18.86 18 5502 22603 46657939

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
Loss of libido 120.05 20.49 33 4714 2009 29945722
Apathy 109.20 20.49 40 4707 6192 29941539
Drug interaction 107.25 20.49 144 4603 199424 29748307
Schizophrenia 104.85 20.49 43 4704 9005 29938726
Psychotic disorder 98.85 20.49 54 4693 21461 29926270
Serotonin syndrome 96.56 20.49 50 4697 17841 29929890
Neuroleptic malignant syndrome 95.08 20.49 48 4699 16247 29931484
Suicidal ideation 84.67 20.49 59 4688 36055 29911676
Obsessive-compulsive disorder 66.72 20.49 25 4722 4116 29943615
Persecutory delusion 53.86 20.49 18 4729 2122 29945609
Toxicity to various agents 51.83 20.49 97 4650 177086 29770645
Depression 50.95 20.49 67 4680 90370 29857361
Weight increased 46.10 20.49 58 4689 74855 29872876
Intentional overdose 42.60 20.49 42 4705 41439 29906292
Catatonia 41.32 20.49 18 4729 4362 29943369
Anxiety 40.75 20.49 60 4687 89811 29857920
Aggression 39.07 20.49 38 4709 36869 29910862
Completed suicide 38.88 20.49 62 4685 99430 29848301
Sopor 38.14 20.49 23 4724 10968 29936763
Salivary hypersecretion 34.73 20.49 19 4728 7547 29940184
Social avoidant behaviour 34.48 20.49 14 4733 2849 29944882
Hanging 34.32 20.49 7 4740 114 29947617
Agitation 33.44 20.49 42 4705 54031 29893700
Suicide attempt 31.94 20.49 34 4713 36663 29911068
Respiratory fatigue 31.61 20.49 6 4741 66 29947665
Obsessive thoughts 31.06 20.49 9 4738 662 29947069
Antipsychotic drug level above therapeutic 30.95 20.49 10 4737 1060 29946671
Akathisia 30.39 20.49 16 4731 5888 29941843
Cyclothymic disorder 30.27 20.49 6 4741 84 29947647
Neonatal behavioural syndrome 28.75 20.49 6 4741 110 29947621
Tic 28.18 20.49 11 4736 2021 29945710
Encephalitis toxic 27.84 20.49 6 4741 129 29947602
Sedation 27.66 20.49 22 4725 16351 29931380
Tremor 26.75 20.49 45 4702 75318 29872413
Heat stroke 24.63 20.49 8 4739 862 29946869
Blood creatine phosphokinase increased 23.88 20.49 32 4715 43816 29903915
Somnolence 23.38 20.49 49 4698 96714 29851017
Drug withdrawal syndrome 22.08 20.49 21 4726 19788 29927943
Impulsive behaviour 21.59 20.49 9 4738 1956 29945775
Mental impairment 21.33 20.49 15 4732 9262 29938469
Cerebellar atrophy 20.87 20.49 6 4741 429 29947302
Inappropriate antidiuretic hormone secretion 20.70 20.49 16 4731 11406 29936325

Pharmacologic Action:

SourceCodeDescription
ATC N06AB08 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Selective serotonin reuptake inhibitors
FDA MoA N0000000109 Serotonin Uptake Inhibitors
FDA EPC N0000175696 Serotonin Reuptake Inhibitor
CHEBI has role CHEBI:35469 thymoanaleptics
CHEBI has role CHEBI:35474 minor tranquilisers
CHEBI has role CHEBI:50949 serotonin reuptake inhibitor
MeSH PA D014151 Anti-Anxiety Agents
MeSH PA D000928 Antidepressive Agents
MeSH PA D018687 Antidepressive Agents, Second-Generation
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D065609 Cytochrome P-450 CYP1A2 Inhibitors
MeSH PA D065689 Cytochrome P-450 CYP2C19 Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018490 Serotonin Agents
MeSH PA D017367 Serotonin Uptake Inhibitors
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Social phobia indication 25501002 DOID:11257
Obsessive-compulsive disorder indication 191736004 DOID:10933
Depressive disorder off-label use 35489007
Posttraumatic stress disorder off-label use 47505003 DOID:2055
Bipolar affective disorder, current episode depression off-label use 191627008 DOID:3312
Suicidal thoughts contraindication 6471006
Bipolar disorder contraindication 13746004 DOID:3312
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Upper gastrointestinal hemorrhage contraindication 37372002
Syndrome of inappropriate vasopressin secretion contraindication 55004003 DOID:3401
Blood coagulation disorder contraindication 64779008 DOID:1247
Epilepsy contraindication 84757009 DOID:1826
Hyponatremia contraindication 89627008
Mania contraindication 231494001
Hypomania contraindication 231496004
Disease of liver contraindication 235856003 DOID:409
Serotonin syndrome contraindication 371089000
Breastfeeding (mother) contraindication 413712001
Poor metabolizer due to cytochrome p450 CYP2D6 variant contraindication 423629005
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.36 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent serotonin transporter Transporter INHIBITOR Ki 8.51 WOMBAT-PK CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 8.84 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.44 CHEMBL
Cytochrome P450 1A2 Enzyme Ki 5.07 WOMBAT-PK
Sodium-dependent noradrenaline transporter Transporter Ki 5.95 PDSP
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.44 CHEMBL
Sodium-dependent serotonin transporter Transporter INHIBITOR Ki 8.19 IUPHAR

External reference:

IDSource
4023976 VUID
N0000021981 NUI
D00824 KEGG_DRUG
61718-82-9 SECONDARY_CAS_RN
4020892 VANDF
4023976 VANDF
C0085228 UMLSCUI
CHEBI:5138 CHEBI
FVX PDB_CHEM_ID
CHEMBL814 ChEMBL_ID
CHEMBL1409 ChEMBL_ID
DB00176 DRUGBANK_ID
D016666 MESH_DESCRIPTOR_UI
9560989 PUBCHEM_CID
7189 IUPHAR_LIGAND_ID
3879 INN_ID
O4L1XPO44W UNII
203143 RXNORM
40916 MMSL
4758 MMSL
d03804 MMSL
003633 NDDF
003634 NDDF
116522003 SNOMEDCT_US
372905008 SNOMEDCT_US
96213009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0228-2848 CAPSULE, EXTENDED RELEASE 100 mg ORAL ANDA 21 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0228-2849 CAPSULE, EXTENDED RELEASE 150 mg ORAL ANDA 21 sections
Fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1670 TABLET, FILM COATED 25 mg ORAL ANDA 34 sections
Fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1671 TABLET, FILM COATED 50 mg ORAL ANDA 34 sections
Fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1672 TABLET, FILM COATED 100 mg ORAL ANDA 34 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 10370-175 CAPSULE, EXTENDED RELEASE 100 mg ORAL ANDA 30 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 10370-176 CAPSULE, EXTENDED RELEASE 150 mg ORAL ANDA 30 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 16590-270 TABLET 25 mg ORAL NDA 11 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 33261-683 TABLET, COATED 50 mg ORAL NDA AUTHORIZED GENERIC 31 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 60505-0164 TABLET 25 mg ORAL ANDA 32 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 60505-0165 TABLET 50 mg ORAL ANDA 32 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 60505-0166 TABLET 100 mg ORAL ANDA 32 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 62559-158 TABLET, COATED 25 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 62559-159 TABLET, COATED 50 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 62559-160 TABLET, COATED 100 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 63629-8018 TABLET, COATED 25 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 68071-2337 TABLET, COATED 50 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 68151-0637 TABLET, COATED 50 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 68788-7219 TABLET, COATED 100 mg ORAL NDA authorized generic 31 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 69452-182 CAPSULE, EXTENDED RELEASE 100 mg ORAL ANDA 22 sections
Fluvoxamine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 69452-183 CAPSULE, EXTENDED RELEASE 150 mg ORAL ANDA 22 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 70518-1057 TABLET, COATED 100 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 70518-1643 TABLET, COATED 50 mg ORAL NDA authorized generic 31 sections
fluvoxamine maleate HUMAN PRESCRIPTION DRUG LABEL 1 71335-0264 TABLET, COATED 100 mg ORAL NDA authorized generic 31 sections