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
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
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
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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. | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE INACTIVE (PARENT)
METABOLITE TOXIC (PARENT)
SALT/SOLVATE (PARENT)
