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H1512

Sigma-Aldrich

Haloperidol

powder

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Synonym(s):
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone, 4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone, 4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone
Empirical Formula (Hill Notation):
C21H23ClFNO2
CAS Number:
Molecular Weight:
375.86
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

powder

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.39 mg/mL
0.1 M HCl: 3 mg/mL
DMSO: soluble
H2O: insoluble
ethanol: soluble

originator

Johnson & Johnson

SMILES string

OC1(CCN(CCCC(=O)c2ccc(F)cc2)CC1)c3ccc(Cl)cc3

InChI

1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

InChI key

LNEPOXFFQSENCJ-UHFFFAOYSA-N

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Application

Haloperidol has been used:
  • in ethanol to serves as an inhibitor of Erg2p
  • to address the mechanism of haloperidol in ferroptosis using hepatocellular carcinoma cells: Hep G2 and Huh-7 cell lines
  • in receptor internalization assay
  • as an antipsychotic drug in Dulbecco′s Modified Eagle medium

Biochem/physiol Actions

Haloperidol is a butyrophenone antipsychotic. It is also classified as a neuroleptic (powerful tranquilizer). Haloperidol acts as a D2, D3, and D4 dopamine receptor antagonist and thus causes Parkinson′s disorder. It also has a negative effect on the central nervous system.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Haloperidol changes mRNA expression of a QKI splice variant in human astrocytoma cells
Jiang L, et al.
BioMed Central Pharmacology, 9(1), 6-6 (2009)
Cdk5 phosphorylates dopamine D2 receptor and attenuates downstream signaling
Jeong J, et al.
Testing, 8(12), e84482-e84482 (2013)
Haloperidol, a sigma receptor 1 antagonist, promotes ferroptosis in hepatocellular carcinoma cells
Bai T, et al.
Biochemical and Biophysical Research Communications, 491(4), 919-925 (2017)
Yeast sphingolipids do not need to contain very long chain fatty acids
Cerantola V, et al.
The Biochemical Journal, 401(1), 205-216 (2007)
CRC Desk Reference of Clinical Pharmacology null

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