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

Stem definitionDrug idCAS RN
1211 2709-56-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • flupentixol hydrochloride
  • flupenthixol
  • fluanxol
  • flupentixol
  • fluxanxol
  • flupentixol dihydrochloride
  • N-7009
  • flupentixol HCl
A thioxanthene neuroleptic that, unlike CHLORPROMAZINE, is claimed to have CNS-activating properties. It is used in the treatment of psychoses although not in excited or manic patients. (From Martindale, The Extra Pharmacopoeia, 30th ed, p595)
  • Molecular weight: 434.52
  • Formula: C23H25F3N2OS
  • CLOGP: 4.34
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 26.71
  • ALOGS: -5.04
  • ROTB: 6

Drug dosage:

DoseUnitRoute
6 mg O
4 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.10 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
CL (Clearance) 4.14 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 34.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1964 YEAR INTRODUCED

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
Blood prolactin abnormal 483.15 38.66 82 2979 1207 46681794
Anosognosia 482.92 38.66 83 2978 1322 46681679
Disturbance in social behaviour 459.00 38.66 82 2979 1649 46681352
Sexual dysfunction 432.15 38.66 82 2979 2321 46680680
Metabolic disorder 382.08 38.66 82 2979 4350 46678651
Personality change 373.63 38.66 83 2978 5175 46677826
Dystonia 296.63 38.66 80 2981 11177 46671824
Suicide attempt 281.77 38.66 113 2948 54923 46628078
Dyskinesia 264.46 38.66 91 2970 28834 46654167
Sedation 256.64 38.66 84 2977 22826 46660175
Schizophrenia 166.43 38.66 48 3013 8520 46674481
Blood glucose increased 163.57 38.66 84 2977 71929 46611072
Insurance issue 93.48 38.66 22 3039 1756 46681245
Extrapyramidal disorder 67.43 38.66 26 3035 11242 46671759
Condition aggravated 60.34 38.66 77 2984 244975 46438026
Drug ineffective 54.10 38.66 129 2932 677709 46005292
Suicidal ideation 52.11 38.66 37 3024 56345 46626656
Hallucination, auditory 44.34 38.66 19 3042 10737 46672264

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
Akathisia 172.31 45.77 48 2474 5856 29944100
Suicide attempt 168.33 45.77 75 2447 36622 29913334
Antipsychotic drug level below therapeutic 165.34 45.77 35 2487 1337 29948619
Therapeutic product effect variable 164.91 45.77 35 2487 1354 29948602
Anosognosia 163.74 45.77 31 2491 663 29949293
Blood prolactin abnormal 161.71 45.77 31 2491 710 29949246
Obsessive-compulsive disorder 159.93 45.77 42 2480 4099 29945857
Disinhibition 152.95 45.77 35 2487 1922 29948034
Disturbance in social behaviour 140.51 45.77 31 2491 1440 29948516
Euphoric mood 130.28 45.77 36 2486 4254 29945702
Increased appetite 125.05 45.77 37 2485 5580 29944376
Metabolic disorder 112.85 45.77 31 2491 3580 29946376
Sexual dysfunction 109.84 45.77 34 2488 5967 29943989
Dyskinesia 104.34 45.77 46 2476 21788 29928168
Dystonia 97.48 45.77 35 2487 9692 29940264
Personality change 88.13 45.77 27 2495 4573 29945383
Weight increased 84.32 45.77 61 2461 74852 29875104
Sedation 83.07 45.77 36 2486 16337 29933619
Hangover 77.37 45.77 18 2504 1060 29948896
Schizophrenia 73.83 45.77 28 2494 9020 29940936
Obesity 64.51 45.77 25 2497 8530 29941426
Drug ineffective 63.86 45.77 107 2415 340280 29609676
Leukopenia 63.72 45.77 46 2476 56113 29893843
Dyslipidaemia 62.62 45.77 22 2500 5705 29944251
Therapeutic product effect incomplete 55.85 45.77 35 2487 33799 29916157
Aggression 50.64 45.77 34 2488 36873 29913083

Pharmacologic Action:

SourceCodeDescription
ATC N05AF01 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Thioxanthene derivatives
CHEBI has role CHEBI:35469 thymoanaleptics
CHEBI has role CHEBI:35474 minor tranquilisers
CHEBI has role CHEBI:37890 alpha-adrenoceptor antagonists
CHEBI has role CHEBI:48561 dopamine blocker
CHEBI has role CHEBI:65190 typical antipsychotic drug
CHEBI has role CHEBI:76779 prolyl oligopeptidase (ec 3.4.21.26) inhibitor
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Schizophrenia indication 58214004 DOID:5419

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.19 Basic
pKa2 4.19 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
D(1A) dopamine receptor GPCR ANTAGONIST Ki 8.40 IUPHAR IUPHAR
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.82 IUPHAR IUPHAR
D(3) dopamine receptor GPCR ANTAGONIST Ki 8.96 IUPHAR
D(1B) dopamine receptor GPCR ANTAGONIST Ki 8.10 IUPHAR
Alpha-1A adrenergic receptor GPCR WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 7.06 PDSP
5-hydroxytryptamine receptor 1A GPCR Ki 5.10 PDSP
Solute carrier family 22 member 1 Transporter IC50 4.05 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor IC50 8.65 CHEMBL
Histamine H1 receptor GPCR Ki 9.07 PDSP
D(4) dopamine receptor GPCR Ki 8.80 PDSP
Dopamine receptor GPCR IC50 8.52 CHEMBL
D(1A) dopamine receptor GPCR IC50 9.52 CHEMBL
D(1A) dopamine receptor GPCR Ki 7.75 CHEMBL

External reference:

IDSource
D01044 KEGG_DRUG
2413-38-9 SECONDARY_CAS_RN
C0016272 UMLSCUI
CHEBI:93235 CHEBI
CHEMBL42055 ChEMBL_ID
CHEMBL54661 ChEMBL_ID
DB00875 DRUGBANK_ID
D005475 MESH_DESCRIPTOR_UI
948 IUPHAR_LIGAND_ID
1745 INN_ID
21HMQ851IS UNII
5281881 PUBCHEM_CID
235742 RXNORM
003477 NDDF
003479 NDDF
387567006 SNOMEDCT_US
442075003 SNOMEDCT_US
96220002 SNOMEDCT_US

Pharmaceutical products:

None