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Details

Stereochemistry ACHIRAL
Molecular Formula C24H25F4NOS
Molecular Weight 451.52
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PIFLUTIXOL

SMILES

OCCC1CCN(CCC=C2C3=CC=C(F)C=C3SC4=C2C=C(C=C4)C(F)(F)F)CC1

InChI

InChIKey=CCUOZZURYIZOKX-FQJNFEMKSA-N
InChI=1S/C24H25F4NOS/c25-18-4-5-20-19(2-1-10-29-11-7-16(8-12-29)9-13-30)21-14-17(24(26,27)28)3-6-22(21)31-23(20)15-18/h2-6,14-16,30H,1,7-13H2/b19-2+

HIDE SMILES / InChI

Molecular Formula C24H25F4NOS
Molecular Weight 451.52
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Piflutixol is a thioxanthene neuroleptic which combines a very potent dopamine antagonistic effect with a potent effect in tests for sedative properties. It was found to have a very strong antagonistic effect against stereotypies induced by dopamine agonists in mice, rats and dogs as well as against apomorphine induced vomiting in dogs. This indicates that piflutixol must be considered as one of the most potent dopamine receptor blocking agents. Piflutixol seems to be the hitherto most potent inhibitor of dopamine-stimulated adenylate cyclase. There was a linear relationship between D-1 dopamine receptor occupation by [3H]piflutixol and inhibition of dopamine sensitive adenylate cyclase. Piflutixol markedly antagonizes the effect of noradrenaline, 5-HT and to some extent histamine, whereas the affinity for muscarinic receptors was rather weak. Piflutixol has a high affinity for dopamine structures within the brain. It is a compound with a very long duration of action.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition of conditional avoidance response by neuroleptics upon repeated administration.
1976 Dec 21
Effect of piflutixol on turnover of catecholamines in mouse brain and rat corpus striatum.
1977 Nov
The pharmacology of a new potent, long acting neuroleptic, piflutixol.
1977 Oct
Selective and stereospecific interactions of R-SK & F 38393 with [3H]piflutixol but not [3H]spiperone binding to striatal D1 and D2 dopamine receptors: comparisons with SCH 23390.
1984 Mar 2
Loss of rat striatal dopamine receptors with ageing is selective for D-2 but not D-1 sites: association with increased non-specific binding of the D-1 ligand [3H]piflutixol.
1984 Oct 1
Characterization of the binding of 3H-SCH 23390, a selective D-1 receptor antagonist ligand, in rat striatum.
1984 Oct 29
Repeated treatment with imipramine decreased the number of [3H]piflutixol binding sites in the rat striatum.
1985 Feb 12
Specific [3H]piflutixol binding to CHAPS-solubilised rat striatal preparations involves dopamine D-2 but not D-1 binding sites.
1986 Feb
Characterization of binding of 3H-SCH 23390 to dopamine D-1 receptors. Correlation to other D-1 and D-2 measures and effect of selective lesions.
1987
Pharmacological characterisation of the dopamine-sensitive adenylate cyclase in cockroach brain: evidence for a distinct dopamine receptor.
1987 Dec 21
Biochemical and pharmacological characterization of [3H]GBR 12935 binding in vitro to rat striatal membranes: labeling of the dopamine uptake complex.
1987 Jun
The hypothermic response of mice to delta-9-tetrahydrocannabinol is enhanced by chlorpromazine, thioxanthenes, alpha-adrenoceptor antagonists and pentolinium but not by SCH 23390 or sulpiride.
1988 Feb
Ontogeny of dopamine D1 receptors in rat striatum.
1988 Mar
The relationship between the occupation of the D-1 dopamine receptor by [3H]piflutixol and the activity of dopamine-sensitive adenylate cyclase in rat striatal membranes.
1991 Jul 5
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:42:50 GMT 2023
Edited
by admin
on Fri Dec 15 15:42:50 GMT 2023
Record UNII
F52O5YF6CA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIFLUTIXOL
INN  
INN  
Official Name English
1-(3-(6-FLUORO-2-(TRIFLUOROMETHYL)THIOXANTHEN-9-YLIDENE)PROPYL)-4-PIPERIDINEETHANOL
Systematic Name English
piflutixol [INN]
Common Name English
Code System Code Type Description
NCI_THESAURUS
C170318
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107162
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
INN
3861
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
CAS
54341-02-5
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
EVMPD
SUB09830MIG
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID20202721
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
MESH
C015448
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
SMS_ID
100000081927
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
PUBCHEM
68714
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
FDA UNII
F52O5YF6CA
Created by admin on Fri Dec 15 15:42:50 GMT 2023 , Edited by admin on Fri Dec 15 15:42:50 GMT 2023
PRIMARY
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