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
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)
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00502Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/015923s079lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00502
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.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16433054
Curator's Comment: Haloperidol was synthesized on the 11th of February 1958 at the Janssen Laboratories, in Belgium.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14611858 |
17.0 nM [EC50] | ||
Target ID: CHEMBL217 Sources: http://www.drugbank.ca/drugs/DB00502 |
|||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7520908 |
53.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | HALDOL Approved UseHALDOL (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 Date1986 |
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Primary | HALDOL Approved UseHALDOL (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 Date1986 |
Doses
Dose | Population | Adverse events |
---|---|---|
0.9 mg single, oral Overdose |
unknown, 11 years n = 1 Health Status: unknown Age Group: 11 years Sex: M Population Size: 1 Sources: |
Other AEs: Drowsiness... |
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) Sources: Electrocardiogram QTc interval prolonged (below serious, 13 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: |
Other AEs: Cheilitis, Constipation... Other AEs: Cheilitis (below serious, 1 patient) Sources: 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Drowsiness | 1 patient | 0.9 mg single, oral Overdose |
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely [Km 33 uM] | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/015923s093s098,018701s071s076lbl.pdf#page=8 Page: (Label) 8, 27 |
major | |||
major | ||||
major | yes (co-administration study) Comment: Coadministration of CYP2D6 inhibitors (chlorpromazine, promethazine, quinidine, paroxetine, sertraline, venlafaxine) increased Haloperidol plasma concentrations. Page: (Label) 9, 28 |
|||
major | yes (co-administration study) Comment: Coadministration of Rifampicin (strong CYP3A4 inducer) decreased plasma Haloperidol levels by a mean of 70%. Page: (Label) 9, 28 |
|||
minor | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25572138
10 uM Haloperidol induced a 54% decrease in the mRNA expression of ABCA1 in murineperitoneal macrophages.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:21:28 GMT 2023
by
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on
Fri Dec 15 16:21:28 GMT 2023
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Record UNII |
6387S86PK3
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Record Status |
Validated (UNII)
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Record Version |
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C66883
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217483
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6387S86PK3
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
HALOPERIDOL LACTATE FROM TABLETS
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Related Record | Type | Details | ||
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ACTIVE MOIETY |