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)
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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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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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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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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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 |
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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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[Recurrent dysregulation of body temperature during antipsychotic pharmacotherapy]. | 2008 Mar |
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Antipsychotics and risk of venous thromboembolism: A population-based case-control study. | 2009 Aug 9 |
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Beyond the dopamine receptor: novel therapeutic targets for treating schizophrenia. | 2010 |
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.
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WHO-ATC |
N05AD05
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QN05AD05
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NCI_THESAURUS |
C28197
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2181
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1893-33-0
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1588
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CHEMBL440294
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DTXSID8048369
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C005569
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m8838
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4830
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100000081961
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33739
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DB09286
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5402501F0W
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78549
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759178
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PIPAMPERONE
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SUB09860MIG
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C73297
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)