halopemide

Names

[ Name ]:
halopemide

[Synonym ]:
halopemide ( N-<2-<4-(5-chloro-2-oxo-1-benzimidazolinyl)piperidino>ethyl>-p-fluorobenzamide )
Halopemidum
Halopemida
N-{2-[4-(5-Chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-4-fluorobenzamide
N-(2-(4-(5-Chloro-2-oxo-1-benzimidazolinyl)piperidino)ethyl)-p-fluorobenzamide
5-chloro-1-{1-[2-(4-fluoro-benzoylamino)-ethyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one
N-2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl-4-fluoro benzamide
N-{2-[4-(5-Chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]ethyl}-4-fluorobenzamide
R 34,301
Benzamide, N-[2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl]-4-fluoro-
halopemide
Halopemide (USAN/INN)
N-[2-[4-(5-Chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl]-4-fluorobenzamide

Biological Activity

[Description]:

Halopemide is a potent phospholipase D (PLD) inhibitor, with IC50s of 220 and 310 nM for human PLD1 and PLD2, respectively. Halopemid is a dopamine receptors antagonist, and acts a psychotropic agent[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

[Target]

PLD1:220 nM (IC50)

PLD2:310 nM (IC50)

dopamine receptors

[In Vitro]

Halopemide (1-2 μM; 21 day) affects calcification in transdifferentiated MOVAS cells[3].

[In Vivo]

Halopemide (10 mg/kg; p.o.) induces dyskinesias in the majority of monkeys tested[2].

[References]

[1]. Scott SA, et al. Design of isoform-selective phospholipase D inhibitors that modulate cancer cell invasiveness. Nat Chem Biol. 2009 Feb;5(2):108-17.

[2]. Neale R, et al. Acute dyskinesias in monkeys elicited by halopemide, mezilamine and the "antidyskinetic" drugs, oxiperomide and tiapride. Psychopharmacology (Berl). 1981;75(3):254-7.

[3]. Skafi N, et al. Phospholipase D: A new mediator during high phosphate-induced vascular calcification associated with chronic kidney disease. J Cell Physiol. 2019 Apr;234(4):4825-4839.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Molecular Formula ]:
C₂₁H₂₂ClFN₄O₂

[ Molecular Weight ]:
416.876

[ Exact Mass ]:
416.141541

[ PSA ]:
70.13000

[ LogP ]:
4.47

[ Index of Refraction ]:
1.612

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

Articles

CAY10593 inhibits the human P2X7 receptor independently of phospholipase D1 stimulation.

Purinergic Signal. 9(4) , 609-19, (2013)

The P2X7 receptor is a trimeric ATP-gated cation channel important in health and disease. We have observed that the specific phospholipase D (PLD)1 antagonist, CAY10593 impairs P2X7-induced shedding o...

Halopemide, a new psychotropic agent. Cerebral distribution and receptor interactions.

Pharm. Weekbl. Sci. 7(1) , 1-9, (1985)

Halopemide is a new psychotropic agent, a structural analogue of the neuroleptics of the butyrophenone type but with different pharmacological and clinical properties. Preliminary clinical findings in...

Dynamic cation-exchange systems for the separation of drugs derived from butyrophenone and diphenylpiperidine by high-performance liquid chromatography and applied in the determination of halopemide in plasma.

J. Chromatogr. A. 164(2) , 177-85, (1979)

Dynamic (solvent generated) cation-exchange systems for the separation of drugs and main metabolites derived from butyrophenone and diphenylpiperidine (haloperidol, pimozide, halopemide) were investig...