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

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 ( + / - )

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
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
Papaverine, drug-induced stereotypy and catalepsy and biogenic amines in the brain of the rat.
1976 Jul
Effect of angiotensin on the central action of dopamine.
1976 Nov-Dec
Parkinsonism by haloperidol and piribedil.
1978 Oct 31
Effect of drugs influencing central serotonergic mechanisms on haloperidol-induced catalepsy.
1979 Mar 29
Behavioral changes as a result of dotarizine or flunarizine influence on dopaminergic neurotransmission in the striatum.
1998
The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved?
1999
Locomotor activity and accumbens Fos expression driven by ventral hippocampal stimulation require D1 and D2 receptors.
1999
L-701,324, a selective antagonist at the glycine site of the NMDA receptor, counteracts haloperidol-induced muscle rigidity in rats.
1999 Apr
Impaired extrapyramidal function caused by the targeted disruption of retinoid X receptor RXRgamma1 isoform.
1999 Apr
Sexual disturbances during clozapine and haloperidol treatment for schizophrenia.
1999 Apr
Neuroleptic malignant syndrome induced by haloperidol following traumatic brain injury.
1999 Dec
Evidence of sex related differences in the effects of calcium channel blockers on neuroleptic-induced catalepsy in mice.
1999 Feb
Atrophic and static (neurodevelopmental) schizophrenic psychoses: premorbid functioning, symptoms and neuroleptic response.
1999 Jul
Clozapine pretreatment modifies haloperidol-elicited forebrain Fos induction: a regionally-specific double dissociation.
1999 Jun
Interaction between olanzapine and haloperidol.
1999 Jun
The effects of dopamine D2 and D3 antagonists on spontaneous motor activity and morphine-induced hyperactivity in male mice.
1999 Mar
Methamphetamine-associated obsessional symptoms and effective risperidone treatment: a case report.
1999 May
Quinpirole, 8-OH-DPAT and ketanserin modulate catalepsy induced by high doses of atypical antipsychotics.
1999 Nov
The effects of benzamide analogues on cocaine self-administration in rhesus monkeys.
1999 Nov
Actions of adenosine A2A receptor antagonist KW-6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP.
1999 Nov
Efficacy of pramipexole, a new dopamine receptor agonist, to relieve the parkinsonian-like muscle rigidity in rats.
1999 Nov 26
Inhibition of haloperidol-induced catalepsy in rats by root extracts from Piper methysticum F.
1999 Oct
Haloperidol-induced torsade de pointes.
1999 Oct
Enhanced striatal dopamine D(2) receptor-induced [35S]GTPgammaS binding after haloperidol treatment.
1999 Oct 8
Two additional uses for sildenafil in psychiatric patients.
1999 Oct-Dec
A case of leukocytoclastic vasculitis associated with haloperidol.
1999 Sep
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice.
1999 Sep
Risperidone in treatment-refractory schizophrenia.
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
Prolonged upper airway instability in the parenteral use of benzodiazepine with levomepromazine.
2000 Feb
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
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
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
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
Haloperidol-induced catalepsy is influenced by calcium channel antagonists.
2000 May-Jun
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
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 Mon Mar 31 18:25:58 GMT 2025
Edited
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on Mon Mar 31 18:25:58 GMT 2025
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 INTENSOL
Preferred 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
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 Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
Code System Code Type Description
PUBCHEM
16051968
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY
RXCUI
217483
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY RxNorm
SMS_ID
100000086697
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY
DAILYMED
6387S86PK3
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY
NCI_THESAURUS
C78110
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PRIMARY
DRUG BANK
DBSALT001232
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PRIMARY
EVMPD
SUB02453MIG
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID801026594
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PRIMARY
ChEMBL
CHEMBL54
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY
CAS
53515-91-6
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY
FDA UNII
6387S86PK3
Created by admin on Mon Mar 31 18:25:58 GMT 2025 , Edited by admin on Mon Mar 31 18:25:58 GMT 2025
PRIMARY
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