Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H30FN3O2 |
Molecular Weight | 375.4802 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)N3CCCCC3
InChI
InChIKey=AXKPFOAXAHJUAG-UHFFFAOYSA-N
InChI=1S/C21H30FN3O2/c22-18-8-6-17(7-9-18)19(26)5-4-12-24-15-10-21(11-16-24,20(23)27)25-13-2-1-3-14-25/h6-9H,1-5,10-16H2,(H2,23,27)
Molecular Formula | C21H30FN3O2 |
Molecular Weight | 375.4802 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB09286Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/14451236 | https://www.ncbi.nlm.nih.gov/pubmed/21349239 | https://www.ncbi.nlm.nih.gov/pubmed/11672571 | https://www.ncbi.nlm.nih.gov/pubmed/8935801 | http://www.onmeda.fr/medicament/dipiperon-93032319.html
Sources: https://www.drugbank.ca/drugs/DB09286
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/14451236 | https://www.ncbi.nlm.nih.gov/pubmed/21349239 | https://www.ncbi.nlm.nih.gov/pubmed/11672571 | https://www.ncbi.nlm.nih.gov/pubmed/8935801 | http://www.onmeda.fr/medicament/dipiperon-93032319.html
Pipamperone (INN, USAN, BAN), also known as Carpiperone and Floropipamide or Fluoropipamide, and as Floropipamide hydrochloride (JAN), is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia. It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan. Pipamperone acts as an antagonist of the 5-HT2A, 5-HT2B, 5-HT2C D2, D3, D4, α1-adrenergic, and α2-adrenergic receptors. It shows the much higher affinity for the 5-HT2A and D4 receptors over the D2receptor (15-fold in the case of the D4 receptor, and even higher in the case of the 5-HT2A receptor), is regarded as "highly selective" for the former two sites at low doses. Pipamperone has low and likely insignificant affinity for the H1 and mACh receptors, as well as for other serotonin and dopamine receptors. Low-dose pipamperone (5 mg twice daily) has been found to accelerate and enhance the antidepressant effect of citalopram. Pipamperone is approved in some European countries. At its usually recommended antipsychotic dose (120–360 mg/d), it has relatively weak neuroleptic activity because it is only moderately effective as a dopamine D2-receptor antagonist, even at high doses.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11672571 |
7.0 nM [Ki] | ||
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11672571 |
54.0 nM [Ki] | ||
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8935801 |
93.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Dipiperon Approved UseIndication: Short-term treatment of states of agitation and aggression during acute and chronic psychotic states (schizophrenia, chronic non-schizophrenic delirium: paranoid delusions, chronic hallucinatory psychoses). |
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Primary | Dipiperon Approved UseIndication: Short-term treatment of states of agitation and aggression during acute and chronic psychotic states (schizophrenia, chronic non-schizophrenic delirium: paranoid delusions, chronic hallucinatory psychoses). |
PubMed
Title | Date | PubMed |
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Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. | 1996 Mar |
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Different regulation of rat 5-HT(2A) and rat 5-HT(2C) receptors in NIH 3T3 cells upon exposure to 5-HT and pipamperone. | 2001 Aug 3 |
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Potent serotonin (5-HT)(2A) receptor antagonists completely prevent the development of hyperthermia in an animal model of the 5-HT syndrome. | 2001 Jan 26 |
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Antipsychotic-induced extrapyramidal syndromes. Risperidone compared with low- and high-potency conventional antipsychotic drugs. | 2001 Jul |
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Pharmacokinetics of pipamperone from three different tablet formulations. | 2002 |
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Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction. | 2002 Apr |
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[Models of drug treatment in the attention deficit disorder with hyperactivity]. | 2002 Feb |
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Atypical kinetics for a series of putative dopamine antagonists to reverse the low-magnitude Ca2+ phase in the dopamine-bound D2short receptor state. | 2002 Jan |
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Role of 5-HT(2) receptors in the tryptamine-induced 5-HT syndrome in rats. | 2002 Jul |
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Differential-pulse polarography determination of pipamperone in pharmaceutical formulations. | 2002 Nov 7 |
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Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry. | 2003 Dec |
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Quantitative determination of piritramide in human serum applying liquid chromatography-two-stage mass spectrometry. | 2003 Jan 5 |
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Stability indicating LC method for the determination of pipamperone. | 2005 Oct 4 |
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Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor. | 2006 Dec 3 |
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[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations]. | 2006 Jun |
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Management of a severe forceful breather with Rett syndrome using carbogen. | 2006 Nov |
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Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach. | 2006 Oct 20 |
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Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen. | 2007 |
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Hypothermia following antipsychotic drug use. | 2007 Jun |
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[Enuresis in therapy with psychotropic drugs]. | 2007 Sep 5 |
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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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Comparison of matrix effects in HPLC-MS/MS and UPLC-MS/MS analysis of nine basic pharmaceuticals in surface waters. | 2008 May |
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Antipsychotics and risk of venous thromboembolism: A population-based case-control study. | 2009 Aug 9 |
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Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study. | 2009 Dec |
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Beyond the dopamine receptor: novel therapeutic targets for treating schizophrenia. | 2010 |
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Identification and quantification of 30 antipsychotics in blood using LC-MS/MS. | 2010 Aug |
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A field study on 8 pharmaceuticals and 1 pesticide in Belgium: removal rates in waste water treatment plants and occurrence in surface water. | 2010 Jul 15 |
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Analysis of risperidone and its metabolite in plasma and saliva by LC with coulometric detection and a novel MEPS procedure. | 2010 Jun 15 |
Patents
Sample Use Guides
Initial Dose 20 mg (1/2 tablet), Average dosage 40-120 mg (1-3 tablets)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11672571
NIH 3T3 cell lines were cultured in Dulbecco’s modified Eagle medium with 10% heat-inactivated dialysed calf serum (30 min at 56 OC; 5-HT concentration 8 nM.) supplemented with the agonist 5-HT (10 mkM) or the antagonist pipamperone (10 mkM) for 15 min or 48 h. Untreated cells were grown in parallel. Cells were grown on 150 mm petri dishes at 37 OC in a humidified atmosphere containing 5% CO2.
Substance Class |
Chemical
Created
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admin
on
Edited
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Record UNII |
5402501F0W
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C28197
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1588
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C005569
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m8838
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33739
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DB09286
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5402501F0W
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PIPAMPERONE
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SUB09860MIG
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C73297
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ACTIVE MOIETY |