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Details

Stereochemistry ACHIRAL
Molecular Formula C21H23ClFNO2
Molecular Weight 375.864
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALOPERIDOL

SMILES

OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C3=CC=C(Cl)C=C3

InChI

InChIKey=LNEPOXFFQSENCJ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Haloperidol is a phenyl-piperidinyl-butyrophenone that is used primarily to treat schizophrenia and other psychoses. It is also used in schizoaffective disorder, delusional disorders, ballism, and Tourette syndrome (a drug of choice) and occasionally as adjunctive therapy in mental retardation and the chorea of Huntington disease. It is a potent antiemetic and is used in the treatment of intractable hiccups. Haloperidol also exerts sedative and antiemetic activity. Haloperidol principal pharmacological effects are similar to those of piperazine-derivative phenothiazines. The drug has action at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Haloperidol has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity. The precise mechanism whereby the therapeutic effects of haloperidol are produced is not known, but the drug appears to depress the CNS at the subcortical level of the brain, midbrain, and brain stem reticular formation. Haloperidol seems to inhibit the ascending reticular activating system of the brain stem (possibly through the caudate nucleus), thereby interrupting the impulse between the diencephalon and the cortex. The drug may antagonize the actions of glutamic acid within the extrapyramidal system, and inhibitions of catecholamine receptors may also contribute to haloperidol's mechanism of action. Haloperidol may also inhibit the reuptake of various neurotransmitters in the midbrain, and appears to have a strong central antidopaminergic and weak central anticholinergic activity. The drug produces catalepsy and inhibits spontaneous motor activity and conditioned avoidance behaviours in animals. The exact mechanism of antiemetic action of haloperidol has also not been fully determined, but the drug has been shown to directly affect the chemoreceptor trigger zone (CTZ) through the blocking of dopamine receptors in the CTZ. Haloperidol is marketed under the trade name Haldol among others.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Extrapyramidal reactions and amine metabolites in cerebrospinal fluid during haloperidol and clozapine treatment of schizophrenic patients.
1975
A comparative study of haloperidol and chlorpromazine in terms of clinical effects and therapeutic reversal with benztropine in schizophrenia. Theoretical implications for potency differences among neuroleptics.
1975 Aug 21
Atypical tardive dyskinesia.
1975 May
Drug-induced dystonia.
1975 May
Effect of drugs influencing central serotonergic mechanisms on haloperidol-induced catalepsy.
1979 Mar 29
Haloperidol-induced within-session response decrement patterns and catalepsy in rats: behavioural dissociation.
1999 Feb
Quinpirole, 8-OH-DPAT and ketanserin modulate catalepsy induced by high doses of atypical antipsychotics.
1999 Nov
[The neurochemical mechanisms of the formation and consolidation of haloperidol-induced catalepsy].
1999 Nov-Dec
Detection and mapping of quantitative trait loci for haloperidol-induced catalepsy in a C57BL/6J x DBA/2J F2 intercross.
1999 Sep
The role of metabotropic glutamate receptor (mGluR) ligands in parkinsonian muscle rigidity.
2000
Effect of muscarinic receptor agonists on animal models of psychosis.
2000 Apr
Inhibition by various antipsychotic drugs of the G-protein-activated inwardly rectifying K(+) (GIRK) channels expressed in xenopus oocytes.
2000 Apr
Estrogen priming modulates autoreceptor-mediated potentiation of dopamine uptake.
2000 Aug 11
Effect of genetic cross on the detection of quantitative trait loci and a novel approach to mapping QTLs.
2000 Dec
Sildenafil and erectile dysfunction.
2000 Dec
Risperidone versus haloperidol in psychotic patients with disturbing neuroleptic-induced extrapyramidal symptoms: a double-blind, multi-center trial.
2000 Dec 15
Sub-chronic inhibition of nitric-oxide synthesis modifies haloperidol-induced catalepsy and the number of NADPH-diaphorase neurons in mice.
2000 Jan
Reduced number of striatal neurons expressing preprosomatostatin mRNA in rats with oral dyskinesias after long-term haloperidol administration.
2000 Jan 21
Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex.
2000 Jan 28
Prolactin regulation of tuberoinfundibular dopaminergic neurons: immunoneutralization studies.
2000 Jan 3
Manic episode in an ifosfamide-treated patient.
2000 Jan-Feb
The antidepressive-like effect of oxcarbazepine: possible role of dopaminergic neurotransmission.
2000 Jul
Further evidence that behavioral tests and neuropeptide mRNA and tissue level alterations can differentiate between typical and atypical antipsychotic drugs.
2000 Jul
[Neuropsychiatric symptoms in preventive antimalarial treatment with mefloquine: apropos of 2 cases].
2000 Jul-Aug
Repeated treatment with 8-OH-DPAT induces tolerance to its ability to produce the 5-HT1A behavioural syndrome, but not to its ability to attenuate haloperidol-induced catalepsy.
2000 Jun
Effect of magnesium sulfate on the haloperidol-induced QT prolongation assessed in the canine in vivo model under the monitoring of monophasic action potential.
2000 Jun
Double blind study of tiapride versus haloperidol and placebo in agitation and aggressiveness in elderly patients with cognitive impairment.
2000 Mar
Effect of dopamine agonists and antagonists on the lorazepam withdrawal syndrome in rats.
2000 Mar
Torsades de pointes secondary to intravenous haloperidol after coronary bypass grafting surgery.
2000 Mar
Effects of atypical neuroleptics on sustained attention deficits in schizophrenia: a trial of risperidone versus haloperidol.
2000 Mar
Haloperidol-induced catalepsy is absent in dopamine D(2), but maintained in dopamine D(3) receptor knock-out mice.
2000 Mar 10
Effects of blockade of metabotropic glutamate receptors in the subthalamic nucleus on haloperidol-induced Parkinsonism in rats.
2000 Mar 17
No changes in dopamine D(1) receptor mRNA expressing neurons in the dorsal striatum of rats with oral movements induced by long-term haloperidol administration.
2000 Mar 24
Propiverine-induced Parkinsonism: a case report and a pharmacokinetic/pharmacodynamic study in mice.
2000 May
Doses of olanzapine, risperidone, and haloperidol used in clinical practice: results of a prospective pharmacoepidemiologic study. EFESO Study Group. Estudio Farmacoepidemiologico en la Esquizofrenia con Olanzapina.
2000 May
The safety of olanzapine compared with other antipsychotic drugs: results of an observational prospective study in patients with schizophrenia (EFESO Study). Pharmacoepidemiologic Study of Olanzapine in Schizophrenia.
2000 May
Sex differences in catalepsy: evidence for hormone-dependent postural mechanisms in haloperidol-treated rats.
2000 May
Haloperidol-induced catalepsy is influenced by calcium channel antagonists.
2000 May-Jun
Biperiden hydrochlorate ameliorates dystonia of rats produced by microinjection of sigma ligands into the red nucleus.
2000 Nov
Enhancement of haloperidol-induced catalepsy by nicotine: an investigation of possible mechanisms.
2000 Nov
Role of prolactin in chloro-S-triazine rat mammary tumorigenesis.
2000 Nov
Contrasting patterns and cellular specificity of transcriptional regulation of the nuclear receptor nerve growth factor-inducible B by haloperidol and clozapine in the rat forebrain.
2000 Oct
The effects of olanzapine, risperidone, and haloperidol on plasma prolactin levels in patients with schizophrenia.
2000 Sep
Effects of antipsychotic drugs on cholecystokinin and preprotachykinin (substance P) mRNA expression in the rat hippocampal formation.
2000 Sep
Haloperidol-induced impotence improved by switching to olanzapine.
2000 Sep-Oct
FosB in rat striatum: normal regional distribution and enhanced expression after 6-month haloperidol administration.
2001 Feb
Increased dopamine d(2) receptor occupancy and elevated prolactin level associated with addition of haloperidol to clozapine.
2001 Feb
Neurotensin gene expression and behavioral responses following administration of psychostimulants and antipsychotic drugs in dopamine D(3) receptor deficient mice.
2001 Feb
The role of the D(2) dopamine receptor (D(2)R) in A(2A) adenosine receptor (A(2A)R)-mediated behavioral and cellular responses as revealed by A(2A) and D(2) receptor knockout mice.
2001 Feb 13
Double activity imaging reveals distinct cellular targets of haloperidol, clozapine and dopamine D(3) receptor selective RGH-1756.
2001 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Parenteral medication, administered intramuscularly in doses of 2 to 5 mg, is utilized for prompt control of the acutely agitated schizophrenic patient with moderately severe to very severe symptoms. Depending on the response of the patient, subsequent doses may be given, administered as often as every hour, although 4 to 8 hour intervals may be satisfactory.
Route of Administration: Intramuscular
In Vitro Use Guide
10 uM Haloperidol induced a 54% decrease in the mRNA expression of ABCA1 in murineperitoneal macrophages.
Name Type Language
HALOPERIDOL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
HALOPERIDOL DECANOATE SPECIFIED IMPURITY G [EP]
Common Name English
HALOPERIDOL COMPONENT OF VESALIUM
Brand Name English
EUKYSTOL
Common Name English
VESALIUM COMPONENT HALOPERIDOL
Brand Name English
HALOPERIDOL [HSDB]
Common Name English
HALOPERIDOL [WHO-IP]
Common Name English
SIGAPERIDOL
Common Name English
HALDOL
Brand Name English
KESELAN
Common Name English
ALOPERIDIN
Common Name English
HALOPERIDOL [WHO-DD]
Common Name English
NSC-170973
Code English
MCN-JR-1625
Code English
R-1625
Code English
NSC-615296
Code English
HALOPERIDOLUM [WHO-IP LATIN]
Common Name English
SERENELFI
Common Name English
SERENASE
Common Name English
BIOPERIDOLO
Common Name English
1-BUTANONE, 4-(4-(4-CHLOROPHENYL)-4-HYDROXY-1-PIPERIDINYL)-1-(4-FLUOROPHENYL)-
Systematic Name English
HALOPERIDOL [USP]
Common Name English
HALOPERIDOL [MI]
Common Name English
SERENACE
Common Name English
HALOPERIDOL DECANOATE IMPURITY, HALOPERIDOL- [USP]
Common Name English
HALOPERIDOL [MART.]
Common Name English
NEURODOL
Common Name English
LINTON
Common Name English
HALOPERIDOL [EP]
Common Name English
HALOPERIDOL [ORANGE BOOK]
Common Name English
HALOPERIDOL [USAN]
Common Name English
HALOPERIDOL [INN]
Common Name English
HALOPERIDOL [VANDF]
Common Name English
DOZIC
Common Name English
HALOPERIDOL [USP-RS]
Common Name English
Classification Tree Code System Code
LIVERTOX 476
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
NDF-RT N0000180182
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
WHO-ATC N05AD01
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 24.1
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
WHO-VATC QN05AD01
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
NCI_THESAURUS C323
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
NCI_THESAURUS C66883
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
HALOPERIDOL
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY Description: A white to faintly yellowish, amorphous or microcrystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 50 parts of ethanol (~750 g/l) TS and in 200 parts of ether R. Category: Neuroleptic. Storage: Haloperidol should be kept in a well-closed container, protected from light. Definition: Haloperidol contains not less than 98.0% and not more than 101.0% of C21H23ClFNO2, calculated with reference to the dried substance.
IUPHAR
86
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
DRUG BANK
DB00502
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
HSDB
52-86-8
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
WIKIPEDIA
HALOPERIDOL
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
RXCUI
5093
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY RxNorm
CAS
52-86-8
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
PUBCHEM
3559
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
ChEMBL
CHEMBL54
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
MESH
D006220
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
LactMed
52-86-8
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-155-6
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
MERCK INDEX
M5904
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C537
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
EPA CompTox
52-86-8
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
EVMPD
SUB08005MIG
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY
INN
918
Created by admin on Tue Oct 22 00:45:20 UTC 2019 , Edited by admin on Tue Oct 22 00:45:20 UTC 2019
PRIMARY