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Details

Stereochemistry ACHIRAL
Molecular Formula C21H22ClFN4O2
Molecular Weight 416.876
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALOPEMIDE

SMILES

FC1=CC=C(C=C1)C(=O)NCCN2CCC(CC2)N3C(=O)NC4=C3C=CC(Cl)=C4

InChI

InChIKey=NBHPRWLFLUBAIE-UHFFFAOYSA-N
InChI=1S/C21H22ClFN4O2/c22-15-3-6-19-18(13-15)25-21(29)27(19)17-7-10-26(11-8-17)12-9-24-20(28)14-1-4-16(23)5-2-14/h1-6,13,17H,7-12H2,(H,24,28)(H,25,29)

HIDE SMILES / InChI
Molecular Formula C21H22ClFN4O2
Molecular Weight 416.876
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Halopemide is a new psychotropic agent, a structural analog of the neuroleptics of the butyrophenone type but with different pharmacological and clinical properties. Preliminary clinical findings indicate that halopemide lacks the ability to induce parkinsonism and may be an effective drug in the treatment of psychosis characterized by autism, emotional withdrawal or apathy. However, the results from of the double-blind study showed no significant difference between the placebo phase and halopemide phase. Halopemide is phospholipase D2 inhibitor: PLD1 and PLD2. Halopemide may be used as a screen to identify inhibitors of human PLD2 using an in vitro biochemical assay. It is also inhibitory at benzodiazepine binding sites.

CNS Activity

CNS Active
4002
Curator's Comment: Known to be CNS active in rats. Human data not available

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Phospholipase D1
1
Target ID: Q13393
Gene ID: 5337.0
Gene Symbol: PLD1
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 21.0 nM [IC50]
Phospholipase D2
1
Target ID: O14939
Gene ID: 5338.0
Gene Symbol: PLD2
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 300.0 nM [IC50]
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
5-Fluoro-2-indolyl des-chlorohalopemide (FIPI), a phospholipase D pharmacological inhibitor that alters cell spreading and inhibits chemotaxis.
2009-03
Optimization of halopemide for phospholipase D2 inhibition.
2007-04-15
Possible individual and gender differences in the small increases in plasma prolactin levels seen during clozapine treatment.
2004-10
Regional distribution of halopemide, a new psychotropic agent, in the rat brain at different time intervals and after chronic administration.
1979-02-12
Effects of halopemide, a new psychotropic agent, on the uptake of serotonin by blood platelets.
1979-02
Regional localization of halopemide, a new psychotropic agent, in the rat brain.
1978-08-15
Patents

Patents

US4031226
1
US5955459
8

Sample Use Guides

In Vivo Use Guide
(2 X 10 mg/day) and the double (2 X 20 mg/day) dose
Route of Administration: Oral
In Vitro Use Guide
The effects of halopemide on the release of 3H-serotonin, 3H-noradrenaline, 3H-acetylcholine and 3H-GABA from rat frontal cortical slices in vitro were studied and compared to those of its neuroleptic congener R29800, spiperone and haloperidol. Spontaneous 3H-serotonin and to a lesser extend 3H-noradrenaline outflow were augmented by the agents, while the effects on basal 3H-acetylcholine and 3H-GABA release were small or absent.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:58:57 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:57 GMT 2025
Record UNII
65Q28TV0ZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-354856
Preferred Name English
HALOPEMIDE
INN   USAN  
INN   USAN  
Official Name English
BENZAMIDE, N-(2-(4-(5-CHLORO-2,3-DIHYDRO-2-OXO-1H-BENZIMIDAZOL-1-YL)-1-PIPERIDINYL)ETHYL)-4-FLUORO-
Systematic Name English
halopemide [INN]
Common Name English
HALOPEMIDE [USAN]
Common Name English
R 34,301
Code English
N-(2-(4-(5-CHLORO-2-OXO-1-BENZIMIDAZOLINYL)PIPERIDINO)ETHYL)-P-FLUOROBENZAMIDE
Common Name English
R-34301
Code English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
Code System Code Type Description
NSC
354856
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
EVMPD
SUB08003MIG
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
NCI_THESAURUS
C65840
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
MESH
C017357
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
FDA UNII
65Q28TV0ZY
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
CAS
59831-65-1
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
SMS_ID
100000083924
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
INN
4253
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
ChEMBL
CHEMBL245621
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
PUBCHEM
65490
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
EPA CompTox
DTXSID20208561
Created by admin on Mon Mar 31 17:58:57 GMT 2025 , Edited by admin on Mon Mar 31 17:58:57 GMT 2025
PRIMARY
Related Record Type Details
Structure of HALOPEMIDE
ACTIVE MOIETY
NIH
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