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H3041

Sigma-Aldrich

Halopemide

≥98% (HPLC)

Synonym(s):

N-(2-(4-(5-Chloro-2-oxo-1-benzimidazolinyl)piperidino)ethyl)-p-fluorobenzamide

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About This Item

Empirical Formula (Hill Notation):
C21H22ClFN4O2
CAS Number:
59831-65-1
Molecular Weight:
416.88
MDL number:
MFCD00866684
UNSPSC Code:
12352204
PubChem Substance ID:
329815189
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

Fc1ccc(cc1)C(=O)NCCN2CCC(CC2)N3C(=O)Nc4cc(Cl)ccc34

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)

InChI key

NBHPRWLFLUBAIE-UHFFFAOYSA-N

Application

Halopemide, a non-specific phospholipase D (PLD) antagonist, may be used with selective PLD antagonists (CAY10593, a PLD1 antagonist; CAY10594 or ML298, selective PLD2 antagonist) to help define the role and physiological effects regulated by phospholipase D enzymes. Halopemide may be used as the basis of the design and development of more selective PLD antagonists.

Biochem/physiol Actions

Halopemide is a dopamine receptor antagonist and a phospholipase D2 inhibitor. 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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A J Loonen et al.
Archives internationales de pharmacodynamie et de therapie, 247(1), 43-58 (1980-09-01)
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
Effects of halopemide on GABA receptor binding, uptake and release.
A J Loonen et al.
Brain research, 210(1-2), 485-492 (1981-04-06)
R Neale et al.
Psychopharmacology, 75(3), 254-257 (1981-01-01)
Oxiperomide and tiapride are dopamine receptor antagonists claimed to have "antidyskinetic" properties in animal models and the clinic. Halopemide and mezilamine are other dopamine antagonists predicted to lack extrapyramidal side effects in man on the basis of animal studies. Acute
A J Loonen et al.
Archives internationales de pharmacodynamie et de therapie, 258(1), 51-59 (1982-07-01)
Halopemide inhibits 3H-BZ binding to crude and washed rat forebrain membranes with IC50 values of 16-25 microM. Its putative metabolites are considerably less active. The actions of halopemide are probably not directly related to its ability to interfere with high-affinity
Sarah A. Scott et al.
Probe Reports from the NIH Molecular Libraries Program (2013-06-14)
A diversity-oriented synthesis approach of the neuroleptic drug halopemide, reported to be a phospholipase D2 (PLD2) inhibitor (but later shown to be a dual PLD1/2 inhibitor) afforded ML298 (CID 53393915), a potent, >53-fold PLD2 selective allosteric inhibitor (cellular PLD1, IC
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