Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H23ClFNO2 |
Molecular Weight | 375.8649 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C(CC(=O)c1ccc(cc1)F)CN2CCC(CC2)(c3ccc(cc3)Cl)O
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
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 |
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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 Date5.059584E11 |
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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 Date5.059584E11 |
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 |
---|---|---|
Atypical tardive dyskinesia. | 1975 May |
|
Drug-induced dystonia. | 1975 May |
|
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs. | 1976 Aug |
|
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 |
|
Modulatory effects of PLG and its peptidomimetics on haloperidol-induced catalepsy in rats. | 1999 |
|
Neurotransmitter-mediated open-field behavioral action of CGRP. | 1999 |
|
Synergistic interactions between ampakines and antipsychotic drugs. | 1999 Apr |
|
Neuroleptic malignant syndrome induced by haloperidol following traumatic brain injury. | 1999 Dec |
|
Haloperidol-induced within-session response decrement patterns and catalepsy in rats: behavioural dissociation. | 1999 Feb |
|
Attenuation of haloperidol-induced catalepsy by a 5-HT2C receptor antagonist. | 1999 Feb |
|
Reduced haloperidol does not interfere with the antipsychotic activity of haloperidol in the treatment of acute schizophrenia. | 1999 Jul |
|
Safety of amisulpride (Solian): a review of 11 clinical studies. | 1999 Jul |
|
New and old antipsychotics versus clozapine in a monkey model: adverse effects and antiamphetamine effects. | 1999 Jun |
|
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 |
|
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice. | 1999 Sep |
|
Identification of quantitative trait loci for haloperidol-induced catalepsy on mouse chromosome 14. | 1999 Sep |
|
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 |
|
Prolonged upper airway instability in the parenteral use of benzodiazepine with levomepromazine. | 2000 Feb |
|
Prolactin regulation of tuberoinfundibular dopaminergic neurons: immunoneutralization studies. | 2000 Jan 3 |
|
Manic episode in an ifosfamide-treated patient. | 2000 Jan-Feb |
|
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 dopamine agonists and antagonists on the lorazepam withdrawal syndrome in rats. | 2000 Mar |
|
Propiverine-induced Parkinsonism: a case report and a pharmacokinetic/pharmacodynamic study in mice. | 2000 May |
|
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 |
|
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 |
|
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 |
|
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
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.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
476
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NDF-RT |
N0000180182
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WHO-ATC |
N05AD01
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WHO-ESSENTIAL MEDICINES LIST |
24.1
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WHO-VATC |
QN05AD01
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NCI_THESAURUS |
C323
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NCI_THESAURUS |
C66883
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Code System | Code | Type | Description | ||
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HALOPERIDOL
Created by
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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. | ||
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86
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PRIMARY | |||
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DB00502
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PRIMARY | |||
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3093
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PRIMARY | |||
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Haloperidol
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HALOPERIDOL
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J6292F8L3D
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5093
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52-86-8
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3559
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CHEMBL54
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D006220
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1303002
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200-155-6
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M5904
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PRIMARY | Merck Index | ||
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C537
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PRIMARY | |||
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52-86-8
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SUB08005MIG
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918
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1353
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE INACTIVE (PARENT)
METABOLITE TOXIC (PARENT)
SALT/SOLVATE (PARENT)