Identification

Name
Flupentixol
Accession Number
DB00875
Description

Flupentixol is an antipsychotic neuroleptic drug. It is a thioxanthene, and therefore closely related to the phenothiazines. Its primary use is as a long acting injection given two or three weekly to people with schizophrenia who have a poor compliance with medication and suffer frequent relapses of illness. It is a D1 and D2 receptor antagonist. It is not approved in the United States.

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Thumb
Weight
Average: 434.52
Monoisotopic: 434.163969096
Chemical Formula
C23H25F3N2OS
Synonyms
  • Flupenthixol
  • Flupenthixole
  • Flupentixol
  • Flupentixolo
  • Flupentixolum
External IDs
  • FX 703
  • LC 44
  • LC-44
  • LU 5-110
  • N 7009
  • N-7009

Pharmacology

Indication

For use in the treatment of schizophrenia and depression

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Flupenthixol is an anxiolytic, antidepressive agent and a mood stabilizer. It inhibits the central monoamine receptors, particularly the dopamine D1 and D2 receptors. Therefore, it increases the amount of serotonin and noradrenaline that control mood and thinking, and improves mood.

Mechanism of action

Flupenthixol is a thioxanthene antipsychotic. The mechanism of action of Flupenthixol is not completely understood. Flupenthixol is a powerful antagonist of both D1 and D2 dopamine receptors, and an alpha-adrenergic receptor antagonist. It's antipsychotic activity is thought to be related to blocks postsynaptic dopamine receptors in the CNS.

TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
A5-hydroxytryptamine receptor 2A
antagonist
Humans
ADopamine D1 receptor
antagonist
Humans
UAlpha-1A adrenergic receptor
antagonist
Humans
UMuscarinic acetylcholine receptor M1
antagonist
Humans
Absorption

Fairly slow and incomplete after oral administration

Volume of distribution
Not Available
Protein binding

Highly bound to plasma proteins (>95%)

Metabolism

Mainly hepatic

Route of elimination
Not Available
Half-life

19 to 39 hours

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

LD50=300 mk/kg (Oral in mice); LD50=791 mg/kg (Oral in rats); LD50=87 mk/kg (IV in mice); LD50=37 mg/kg (IV in rats)

Affected organisms
  • Humans and other mammals
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
AcebutololThe risk or severity of QTc prolongation can be increased when Acebutolol is combined with Flupentixol.
AceclofenacThe risk or severity of hypertension can be increased when Flupentixol is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Flupentixol is combined with Acemetacin.
AcenocoumarolThe risk or severity of adverse effects can be increased when Flupentixol is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Flupentixol.
AcetophenazineThe risk or severity of adverse effects can be increased when Flupentixol is combined with Acetophenazine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Flupentixol is combined with Acetylsalicylic acid.
AclidiniumThe risk or severity of adverse effects can be increased when Flupentixol is combined with Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Flupentixol.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Flupentixol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Avoid alcohol.
  • Take with food. Food reduces irritation.

Products

Product Ingredients
IngredientUNIICASInChI Key
Flupentixol decanoate3B2FE28C1W30909-51-4UIKWDDSLMBHIFT-UHFFFAOYSA-N
Flupentixol dihydrochloride96L0Z069N151529-01-2IOVDQEIIMOZNNA-MHKBYHAFSA-N
International/Other Brands
Depixol (Lundbeck A/S) / Fluanxol (Lundbeck A/S) / Jexit (Johnson)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Fluanxol 0.5mg - TabTabletOralLundbeck Inc.1995-12-31Not applicableCanada flag
Fluanxol 3mg - TabTabletOralLundbeck Inc.1995-12-31Not applicableCanada flag
Fluanxol Depot 10%- Liq Im 100mg/mlSolutionIntramuscularLundbeck Inc.1995-12-31Not applicableCanada flag
Fluanxol Depot 2% -liq Im 20mg/mlSolutionIntramuscularLundbeck Inc.1995-12-31Not applicableCanada flag
Fluanxol Depot Inj 100mg/mlLiquidIntramuscularMerrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc1981-12-311996-09-09Canada flag
Fluanxol Depot Inj 20mg/mlLiquidIntramuscularMerrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc1981-12-311996-09-09Canada flag
Fluanxol Tab 0.5mgTabletOralMerrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc1986-12-311996-09-09Canada flag
Fluanxol Tab 3mgTabletOralMerrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc1986-12-311996-09-09Canada flag
Flupentixol Decanoate Injection BPSolutionIntramuscularSandoz Canada Incorporated2009-08-27Not applicableCanada flag
Flupentixol Decanoate Injection BPSolutionIntramuscularSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more

Categories

ATC Codes
N05AF01 — Flupentixol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiopyrans
Sub Class
1-benzothiopyrans
Direct Parent
Thioxanthenes
Alternative Parents
Diarylthioethers / N-alkylpiperazines / Benzenoids / Trialkylamines / 1,2-aminoalcohols / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives
show 1 more
Substituents
1,2-aminoalcohol / 1,4-diazinane / Alcohol / Alkanolamine / Alkyl fluoride / Alkyl halide / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
thioxanthenes (CHEBI:10454)

Chemical Identifiers

UNII
FA0UYH6QUO
CAS number
2709-56-0
InChI Key
NJMYODHXAKYRHW-DVZOWYKESA-N
InChI
InChI=1S/C23H25F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,29H,3,9-15H2/b18-5-
IUPAC Name
2-(4-{3-[(9Z)-2-(trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol
SMILES
[H]\C(CCN1CCN(CCO)CC1)=C1/C2=CC=CC=C2SC2=C1C=C(C=C2)C(F)(F)F

References

Synthesis Reference

Smith Kline & French Laboratories; British Patent 925,538; May 8, 1963. Craig, P.N. and Zirkle, C.L.; U.S. Patent 3,282,930; November 1, 1966; assigned to Smith Kline & French Laboratories.

General References
Not Available
KEGG Drug
D01044
KEGG Compound
C11191
PubChem Compound
5281881
PubChem Substance
46507816
ChemSpider
4445173
BindingDB
79172
RxNav
4495
ChEBI
10454
ChEMBL
CHEMBL54661
ZINC
ZINC000029489118
Therapeutic Targets Database
DAP000026
PharmGKB
PA10268
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Flupenthixol
AHFS Codes
  • 28:16.08.32 — Thioxanthenes

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCompliance / Depression / Dyspepsia1
4CompletedTreatmentSchizophrenia1
4CompletedTreatmentTinnitus1
3CompletedTreatmentGlobus1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia1
3Unknown StatusTreatmentPsychosis Nos/Other1
2CompletedTreatmentCocaine-Related Disorders2
2CompletedTreatmentCocaine-Related Disorders / Substance-Related Disorders1
2CompletedTreatmentSubstance-Related Disorders1
1CompletedTreatmentBioequivalence Study in Healthy Subjects1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral500 mcg
Tablet0.5 mg
Tablet3 mg
Tablet, coatedOral3 mg
TabletOral0.25 mg
Tablet, sugar coatedOral0.5 MG
TabletOral
Tablet
Tablet, film coatedOral
Tablet, film coatedOral1 MG
TabletOral1 mg
Tablet, sugar coatedOral
Tablet, coated3 mg
Tablet, film coatedOral5 MG
Injection, solution100 mg/1mL
Injection, solution20 mg/1mL
Injection, suspension, extended release20 mg/1mL
Injection, solutionParenteral100 mg
SolutionIntramuscular
Injection, solutionParenteral100 MG/ML
Injection, solutionParenteral20 mg
Injection, solutionParenteral20 MG/1ML
SolutionIntramuscular20 mg/ml
LiquidIntramuscular
Injection, solutionParenteral100 MG/1ML
Injection, solutionParenteral10 MG/0.5ML
Injection, solutionParenteral
Tablet, film coatedOral0.5 mg
Injection, solutionParenteral200 MG
Injection, solutionParenteral20 MG/ML
Injection, solutionParenteral40 MG/ML
Prices
Unit descriptionCostUnit
Fluanxol Depot 100 mg/ml39.79USD ml
Fluanxol Depot 20 mg/ml7.96USD ml
Fluanxol 3 mg Tablet0.59USD tablet
Fluanxol 0.5 mg Tablet0.27USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility0.000346 mg/mlNot Available
logP4.51HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00399 mg/mLALOGPS
logP4.56ALOGPS
logP4.5ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.71 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity128.17 m3·mol-1ChemAxon
Polarizability44.79 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9825
Blood Brain Barrier+0.9778
Caco-2 permeable-0.5438
P-glycoprotein substrateSubstrate0.8762
P-glycoprotein inhibitor IInhibitor0.92
P-glycoprotein inhibitor IIInhibitor0.859
Renal organic cation transporterInhibitor0.5065
CYP450 2C9 substrateNon-substrate0.8084
CYP450 2D6 substrateSubstrate0.804
CYP450 3A4 substrateNon-substrate0.6921
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8933
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.5657
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7748
Ames testNon AMES toxic0.828
CarcinogenicityNon-carcinogens0.8985
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8385 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6624
hERG inhibition (predictor II)Inhibitor0.7962
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706]
  3. Ogren SO, Hall H, Kohler C, Magnusson O, Lindbom LO, Angeby K, Florvall L: Remoxipride, a new potential antipsychotic compound with selective antidopaminergic actions in the rat brain. Eur J Pharmacol. 1984 Jul 20;102(3-4):459-74. [PubMed:6149133]
  4. Arnt J: Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine. Eur J Pharmacol. 1995 Sep 5;283(1-3):55-62. [PubMed:7498321]
  5. Huettl P, Gerhardt GA, Browning MD, Masserano JM: Effects of dopamine receptor agonists and antagonists on catecholamine release in bovine chromaffin cells. J Pharmacol Exp Ther. 1991 May;257(2):567-74. [PubMed:1674528]
  6. Nilsson CL, Ekman A, Hellstrand M, Eriksson E: Inverse agonism at dopamine D2 receptors. Haloperidol-induced prolactin release from GH4C1 cells transfected with the human D2 receptor is antagonized by R(-)-n-propylnorapomorphine, raclopride, and phenoxybenzamine. Neuropsychopharmacology. 1996 Jul;15(1):53-61. [PubMed:8797192]
  7. Reimold M, Solbach C, Noda S, Schaefer JE, Bartels M, Beneke M, Machulla HJ, Bares R, Glaser T, Wormstall H: Occupancy of dopamine D(1), D (2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol. Psychopharmacology (Berl). 2007 Feb;190(2):241-9. Epub 2006 Nov 17. [PubMed:17111172]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Reimold M, Solbach C, Noda S, Schaefer JE, Bartels M, Beneke M, Machulla HJ, Bares R, Glaser T, Wormstall H: Occupancy of dopamine D(1), D (2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol. Psychopharmacology (Berl). 2007 Feb;190(2):241-9. Epub 2006 Nov 17. [PubMed:17111172]
Details
3. Dopamine D1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Cai G, Gurdal H, Smith C, Wang HY, Friedman E: Inverse agonist properties of dopaminergic antagonists at the D(1A) dopamine receptor: uncoupling of the D(1A) dopamine receptor from G(s) protein. Mol Pharmacol. 1999 Nov;56(5):989-96. [PubMed:10531405]
  4. Reimold M, Solbach C, Noda S, Schaefer JE, Bartels M, Beneke M, Machulla HJ, Bares R, Glaser T, Wormstall H: Occupancy of dopamine D(1), D (2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol. Psychopharmacology (Berl). 2007 Feb;190(2):241-9. Epub 2006 Nov 17. [PubMed:17111172]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
This is a possible target based on the general actions of drugs in the arylpiperazine drug class.
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Li X, Murray WV, Jolliffe L, Pulito V: Novel arylpiperazines as selective alpha1-adrenergic receptor antagonists. Bioorg Med Chem Lett. 2000 May 15;10(10):1093-6. doi: 10.1016/s0960-894x(00)00169-4. [PubMed:10843225]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Golds PR, Przyslo FR, Strange PG: The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors. Br J Pharmacol. 1980 Mar;68(3):541-9. [PubMed:7052344]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name
DDC
Uniprot ID
P20711
Uniprot Name
Aromatic-L-amino-acid decarboxylase
Molecular Weight
53925.815 Da
References
  1. Zhu MY, Juorio AV, Paterson IA, Boulton AA: Regulation of aromatic L-amino acid decarboxylase in rat striatal synaptosomes: effects of dopamine receptor agonists and antagonists. Br J Pharmacol. 1994 May;112(1):23-30. [PubMed:7913379]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Hait WN, Gesmonde JF, Murren JR, Yang JM, Chen HX, Reiss M: Terfenadine (Seldane): a new drug for restoring sensitivity to multidrug resistant cancer cells. Biochem Pharmacol. 1993 Jan 26;45(2):401-6. [PubMed:8094615]
  2. Dey S, Hafkemeyer P, Pastan I, Gottesman MM: A single amino acid residue contributes to distinct mechanisms of inhibition of the human multidrug transporter by stereoisomers of the dopamine receptor antagonist flupentixol. Biochemistry. 1999 May 18;38(20):6630-9. [PubMed:10350482]
  3. Hafkemeyer P, Licht T, Pastan I, Gottesman MM: Chemoprotection of hematopoietic cells by a mutant P-glycoprotein resistant to a potent chemosensitizer of multidrug-resistant cancers. Hum Gene Ther. 2000 Mar 1;11(4):555-65. [PubMed:10724034]
  4. Yang JM, Vassil A, Hait WN: Involvement of phosphatidylinositol-3-kinase in membrane ruffling induced by P-glycoprotein substrates in multidrug-resistant carcinoma cells. Biochem Pharmacol. 2002 Mar 1;63(5):959-66. [PubMed:11911848]
  5. Ford JM, Bruggemann EP, Pastan I, Gottesman MM, Hait WN: Cellular and biochemical characterization of thioxanthenes for reversal of multidrug resistance in human and murine cell lines. Cancer Res. 1990 Mar 15;50(6):1748-56. [PubMed:1968358]
  6. Ford JM, Yang JM, Hait WN: Effect of buthionine sulfoximine on toxicity of verapamil and doxorubicin to multidrug resistant cells and to mice. Cancer Res. 1991 Jan 1;51(1):67-72. [PubMed:1988108]

Drug created on June 13, 2005 07:24 / Updated on October 26, 2020 22:41

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