U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry UNKNOWN
Molecular Formula C21H23ClFNO2.C3H6O3
Molecular Weight 465.942
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALOPERIDOL LACTATE

SMILES

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

InChI

InChIKey=BVUSNQJCSYDJJG-UHFFFAOYSA-N
InChI=1S/C21H23ClFNO2.C3H6O3/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;1-2(4)3(5)6/h3-10,26H,1-2,11-15H2;2,4H,1H3,(H,5,6)

HIDE SMILES / InChI

Molecular Formula C3H6O3
Molecular Weight 90.0779
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C21H23ClFNO2
Molecular Weight 375.864
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/015923s079lbl.pdf

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.

Originator

Curator's Comment: Haloperidol was synthesized on the 11th of February 1958 at the Janssen Laboratories, in Belgium.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
17.0 nM [EC50]
53.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HALDOL

Approved Use

HALDOL (haloperidol) is indicated for use in the treatment of schizophrenia. HALDOL is indicated for the control of tics and vocal utterances of Tourette’s Disorder.

Launch Date

1986
Primary
HALDOL

Approved Use

HALDOL (haloperidol) is indicated for use in the treatment of schizophrenia. HALDOL is indicated for the control of tics and vocal utterances of Tourette’s Disorder.

Launch Date

1986
Doses

Doses

DosePopulationAdverse events​
0.9 mg single, oral
Overdose
Dose: 0.9 mg
Route: oral
Route: single
Dose: 0.9 mg
Sources:
unknown, 11 years
n = 1
Health Status: unknown
Age Group: 11 years
Sex: M
Population Size: 1
Sources:
Other AEs: Drowsiness...
Other AEs:
Drowsiness (1 patient)
Sources:
2 mg 4 times / day multiple, intramuscular
Recommended
Dose: 2 mg, 4 times / day
Route: intramuscular
Route: multiple
Dose: 2 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: dementia-related psychosis
Age Group: adult
Sources:
5 mg 3 times / day multiple, oral
Recommended
Dose: 5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 5 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: dementia-related psychosis
Age Group: adult
Sources:
10 mg 2 times / day steady, intravenous
Dose: 10 mg, 2 times / day
Route: intravenous
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 192
Health Status: unhealthy
Condition: Delirium
Population Size: 192
Sources:
Other AEs: Torsades de pointes, Electrocardiogram QTc interval prolonged...
Other AEs:
Torsades de pointes (serious, 2 patients)
Electrocardiogram QTc interval prolonged (below serious, 13 patients)
Sources:
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Other AEs: Cheilitis, Constipation...
Other AEs:
Cheilitis (below serious, 1 patient)
Constipation (below serious, 2 patients)
Salivary hypersecretion (below serious, 1 patient)
Vomiting (below serious, 1 patient)
Malaise (below serious, 2 patients)
Thirst (below serious, 1 patient)
Fall (below serious, 1 patient)
Blood pressure decreased (below serious, 1 patient)
Weight increased (below serious, 1 patient)
Increased appetite (below serious, 1 patient)
Arthralgia (below serious, 1 patient)
Osteoarthritis (below serious, 1 patient)
Akathisia (below serious, 3 patients)
Dystonia (below serious, 3 patients)
Headache (below serious, 1 patient)
Sedation (below serious, 1 patient)
Tremor (below serious, 2 patients)
Depressive symptom (below serious, 1 patient)
Insomnia (below serious, 1 patient)
Mania (below serious, 1 patient)
Pruritus (below serious, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Drowsiness 1 patient
0.9 mg single, oral
Overdose
Dose: 0.9 mg
Route: oral
Route: single
Dose: 0.9 mg
Sources:
unknown, 11 years
n = 1
Health Status: unknown
Age Group: 11 years
Sex: M
Population Size: 1
Sources:
Electrocardiogram QTc interval prolonged below serious, 13 patients
10 mg 2 times / day steady, intravenous
Dose: 10 mg, 2 times / day
Route: intravenous
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 192
Health Status: unhealthy
Condition: Delirium
Population Size: 192
Sources:
Torsades de pointes serious, 2 patients
10 mg 2 times / day steady, intravenous
Dose: 10 mg, 2 times / day
Route: intravenous
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 192
Health Status: unhealthy
Condition: Delirium
Population Size: 192
Sources:
Arthralgia below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Blood pressure decreased below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Cheilitis below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Depressive symptom below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Fall below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Headache below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Increased appetite below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Insomnia below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Mania below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Osteoarthritis below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Pruritus below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Salivary hypersecretion below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Sedation below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Thirst below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Vomiting below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Weight increased below serious, 1 patient
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Constipation below serious, 2 patients
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Malaise below serious, 2 patients
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Tremor below serious, 2 patients
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Akathisia below serious, 3 patients
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
Dystonia below serious, 3 patients
10 mg 2 times / day steady, oral
Dose: 10 mg, 2 times / day
Route: oral
Route: steady
Dose: 10 mg, 2 times / day
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: Bipolar I Disorder
Population Size: 20
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
moderate [Ki 7.2 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >30 uM]
no [IC50 >50 uM]
no
yes [Activation 31.6228 uM]
yes [IC50 10.7 uM]
yes [IC50 141.9 uM]
yes [IC50 2.87 uM]
yes [IC50 25.3 uM]
yes [IC50 25.4 uM]
yes [IC50 3.6 uM]
yes [IC50 4.69 uM]
yes [IC50 8.2 uM]
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely [Km 33 uM]
major
major
major
major
minor
minor
minor
no
no
no
no
yes
yes
yes
yes
yes
yes
yes
Tox targets
PubMed

PubMed

TitleDatePubMed
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs.
1976 Aug
Effect of drugs influencing central serotonergic mechanisms on haloperidol-induced catalepsy.
1979 Mar 29
Modulatory effects of PLG and its peptidomimetics on haloperidol-induced catalepsy in rats.
1999
Antipsychotic profile of alstonine: ethnopharmacology of a traditional Nigerian botanical remedy.
1999
Neurotransmitter-mediated open-field behavioral action of CGRP.
1999
Impaired extrapyramidal function caused by the targeted disruption of retinoid X receptor RXRgamma1 isoform.
1999 Apr
Synergistic interactions between ampakines and antipsychotic drugs.
1999 Apr
Haloperidol-induced within-session response decrement patterns and catalepsy in rats: behavioural dissociation.
1999 Feb
Evidence of sex related differences in the effects of calcium channel blockers on neuroleptic-induced catalepsy in mice.
1999 Feb
Effects of local application of 5-hydroxytryptamine into the dorsal or median raphe nuclei on haloperidol-induced catalepsy in the rat.
1999 Jan
GlycineB antagonists and partial agonists in rodent models of Parkinson's disease--comparison with uncompetitive N-methyl-D-aspartate receptor antagonist.
1999 Jan
Safety of amisulpride (Solian): a review of 11 clinical studies.
1999 Jul
Atrophic and static (neurodevelopmental) schizophrenic psychoses: premorbid functioning, symptoms and neuroleptic response.
1999 Jul
New and old antipsychotics versus clozapine in a monkey model: adverse effects and antiamphetamine effects.
1999 Jun
The effects of dopamine D2 and D3 antagonists on spontaneous motor activity and morphine-induced hyperactivity in male mice.
1999 Mar
Molecular and behavioral effects mediated by Gs-coupled adenosine A2a, but not serotonin 5-Ht4 or 5-Ht6 receptors following antipsychotic administration.
1999 Mar
Behavioral effects following single and combined maternal exposure to PCB 77 (3,4,3',4'-tetrachlorobiphenyl) and PCB 47 (2,4,2',4'-tetrachlorobiphenyl) in rats.
1999 Mar-Apr
Quinpirole, 8-OH-DPAT and ketanserin modulate catalepsy induced by high doses of atypical antipsychotics.
1999 Nov
Actions of adenosine A2A receptor antagonist KW-6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP.
1999 Nov
[The neurochemical mechanisms of the formation and consolidation of haloperidol-induced catalepsy].
1999 Nov-Dec
Inhibition of haloperidol-induced catalepsy in rats by root extracts from Piper methysticum F.
1999 Oct
Two additional uses for sildenafil in psychiatric patients.
1999 Oct-Dec
A case of leukocytoclastic vasculitis associated with haloperidol.
1999 Sep
Identification of quantitative trait loci for haloperidol-induced catalepsy on mouse chromosome 14.
1999 Sep
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
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
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
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
Effects of atypical neuroleptics on sustained attention deficits in schizophrenia: a trial of risperidone versus haloperidol.
2000 Mar
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
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
Haloperidol-induced impotence improved by switching to olanzapine.
2000 Sep-Oct
Neurotensin gene expression and behavioral responses following administration of psychostimulants and antipsychotic drugs in dopamine D(3) receptor deficient mice.
2001 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: can also be taken orally https://www.drugs.com/ppa/haloperidol.html
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
10 uM Haloperidol induced a 54% decrease in the mRNA expression of ABCA1 in murineperitoneal macrophages.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:21:28 GMT 2023
Edited
by admin
on Fri Dec 15 16:21:28 GMT 2023
Record UNII
6387S86PK3
Record Status Validated (UNII)
Record Version
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Name Type Language
HALOPERIDOL LACTATE
ORANGE BOOK   VANDF   WHO-DD  
Common Name English
(±)-HALOPERIDOL LACTATE
Common Name English
HALOPERIDOL LACTATE [VANDF]
Common Name English
Haloperidol lactate [WHO-DD]
Common Name English
HALOPERIDOL LACTATE, (±)-
Common Name English
PROPANOIC ACID, 2-HYDROXY-, COMPD. WITH 4-(4-(4-CHLOROPHENYL)-4-HYDROXY-1-PIPERIDINYL)-1-(4-FLUOROPHENYL)-1-BUTANONE (1:1)
Common Name English
HALOPERIDOL INTENSOL
Brand Name English
1-BUTANONE, 4-(4-(4-CHLOROPHENYL)-4-HYDROXY-1-PIPERIDINYL)-1-(4-FLUOROPHENYL)-, 2-HYDROXYPROPANOATE (SALT)
Common Name English
HALOPERIDOL LACTATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 16:21:28 GMT 2023 , Edited by admin on Fri Dec 15 16:21:28 GMT 2023
Code System Code Type Description
PUBCHEM
16051968
Created by admin on Fri Dec 15 16:21:28 GMT 2023 , Edited by admin on Fri Dec 15 16:21:28 GMT 2023
PRIMARY
RXCUI
217483
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PRIMARY RxNorm
SMS_ID
100000086697
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PRIMARY
DAILYMED
6387S86PK3
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PRIMARY
NCI_THESAURUS
C78110
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PRIMARY
DRUG BANK
DBSALT001232
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PRIMARY
EVMPD
SUB02453MIG
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PRIMARY
EPA CompTox
DTXSID801026594
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PRIMARY
ChEMBL
CHEMBL54
Created by admin on Fri Dec 15 16:21:28 GMT 2023 , Edited by admin on Fri Dec 15 16:21:28 GMT 2023
PRIMARY
CAS
53515-91-6
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PRIMARY
FDA UNII
6387S86PK3
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PRIMARY
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