Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H24FN3O2 |
Molecular Weight | 381.4433 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
FC1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)N3C(=O)NC4=CC=CC=C34
InChI
InChIKey=FEBOTPHFXYHVPL-UHFFFAOYSA-N
InChI=1S/C22H24FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28)
Molecular Formula | C22H24FN3O2 |
Molecular Weight | 381.4433 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Benperidol is a relatively old antipsychotic drug that has been marketed since 1966. It has been used in Germany for 30 years, but is also available in Belgium, Greece, Italy, the Netherlands and the UK. Benperidol is a drug which is a highly potent butyrophenone derivative. It is the most potent neuroleptic on the European market, with chlorpromazine equivalency as high as 75 to 100 (about 150 to 200% potency in terms of dose compared to haloperidol). Benperidol was discovered at Janssen Pharmaceutica in 1961. Benperidol is a potent dopamine receptor antagonist, with a high affinity for the D2-sites. The antipsychotic effects of this drug are primarily due to blockade of the D receptors. In terms of D receptor blockade, benperidol is one of the most potent antipsychotic agents, being approximately eight times more potent than haloperidol. Benperidol also acts as a dopamine antagonist in the chemoreceptor trigger zone, giving rise to antiemetic properties. It is also a weak antagonist at muscarinic, histamine H1, and alpha1-adrenoceptors. Adverse effects include extrapyramidal side effects and tardive dykinesia
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL217 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15846648 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Drug-induced asterixis amplified by relative hypoglycemia]. | 1996 Apr |
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In vivo measurement of D2 receptor density and affinity for 18F-(3-N-methyl)benperidol in the rat striatum with a PET system for small laboratory animals. | 2003 Apr |
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Bilateral increase in striatal dopamine D2 receptor density in the 6-hydroxydopamine-lesioned rat: a serial in vivo investigation with small animal PET. | 2003 Mar |
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Complete dopamine D2 receptor occupancy without extrapyramidal side effects under benperidol. | 2004 Feb |
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Olanzapine plasma concentration, average daily dose, and interaction with co-medication in schizophrenic patients. | 2004 Mar |
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Benperidol for schizophrenia. | 2005 Apr 18 |
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Synthesis and characterization of selective dopamine D2 receptor antagonists. | 2006 Feb 1 |
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Amisulpride-induced hyperprolactinaemia is not reversed by addition of aripiprazole. | 2007 Feb |
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Validation of the reference tissue model for estimation of dopaminergic D2-like receptor binding with [18F](N-methyl)benperidol in humans. | 2008 Apr |
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The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913). | 2008 Dec 22 |
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[Recurrent dysregulation of body temperature during antipsychotic pharmacotherapy]. | 2008 Mar |
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Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626. | 2010 Jul 15 |
Patents
Substance Class |
Chemical
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admin
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Edited
Fri Dec 15 15:01:31 UTC 2023
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Fri Dec 15 15:01:31 UTC 2023
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Record UNII |
97O6X78C53
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Record Status |
Validated (UNII)
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WHO-VATC |
QN05AD07
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WHO-ATC |
N05AD07
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NCI_THESAURUS |
C66883
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100000086355
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97O6X78C53
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D001544
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CHEMBL297302
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DB12867
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BENPERIDOL
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DTXSID7045364
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C81086
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SUB05727MIG
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218-172-2
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1577
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Related Record | Type | Details | ||
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ACTIVE MOIETY |