Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H30FN3O2.2ClH |
Molecular Weight | 448.402 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.NC(=O)C1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)N3CCCCC3
InChI
InChIKey=BMXXSXQVMCXGJM-UHFFFAOYSA-N
InChI=1S/C21H30FN3O2.2ClH/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);2*1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|---|
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). |
|||
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 |
---|---|---|
Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. | 1996 Mar |
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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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Differential-pulse polarography determination of pipamperone in pharmaceutical formulations. | 2002 Nov 7 |
|
In-patient psychiatric-psychotherapeutic treatment of mothers with a generalized anxiety disorder--does the co-admission of their children influence the treatment results? A prospective, controlled study. | 2004 Nov 30 |
|
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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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 |
|
[Enuresis in therapy with psychotropic drugs]. | 2007 Sep 5 |
|
Evaluation of serotonin-2A receptor occupancy with 123I-5-I-R91150 and single-photon emission tomography before and after low-dose pipamperone administration in the canine brain. | 2008 Aug |
|
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 |
|
[Recurrent dysregulation of body temperature during antipsychotic pharmacotherapy]. | 2008 Mar |
|
Comparison of matrix effects in HPLC-MS/MS and UPLC-MS/MS analysis of nine basic pharmaceuticals in surface waters. | 2008 May |
|
Antipsychotics and risk of venous thromboembolism: A population-based case-control study. | 2009 Aug 9 |
|
Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study. | 2009 Dec |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Antipsychotic use and the risk of hip/femur fracture: a population-based case-control study. | 2009 Sep |
|
Beyond the dopamine receptor: novel therapeutic targets for treating schizophrenia. | 2010 |
|
Identification and quantification of 30 antipsychotics in blood using LC-MS/MS. | 2010 Aug |
|
Clinical trials in CNS--SMi's eighth annual conference. | 2010 Feb |
|
Rationale and design of the randomised clinical trial comparing early medication change (EMC) strategy with treatment as usual (TAU) in patients with major depressive disorder--the EMC trial. | 2010 Feb 26 |
|
Gene expression of NMDA receptor subunits in the cerebellum of elderly patients with schizophrenia. | 2010 Mar |
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
by
admin
on
Edited
Fri Dec 15 18:37:58 UTC 2023
by
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on
Fri Dec 15 18:37:58 UTC 2023
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Record UNII |
IT085U64JB
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Record Status |
Validated (UNII)
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100000085607
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CHEMBL440294
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