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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
Structure of PIPAMPERONE HYDROCHLORIDE

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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.0 nM [Ki]
54.0 nM [Ki]
93.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dipiperon

Approved Use

Indication: 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 Use

Indication: 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

PubMed

TitleDatePubMed
Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding.
1996 Mar
[Models of drug treatment in the attention deficit disorder with hyperactivity].
2002 Feb
Differential-pulse polarography determination of pipamperone in pharmaceutical formulations.
2002 Nov 7
Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry.
2003 Dec
Quantitative determination of piritramide in human serum applying liquid chromatography-two-stage mass spectrometry.
2003 Jan 5
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
Unbiased descriptor and parameter selection confirms the potential of proteochemometric modelling.
2005 Mar 10
Tackling matrix effects during development of a liquid chromatographic-electrospray ionisation tandem mass spectrometric analysis of nine basic pharmaceuticals in aqueous environmental samples.
2006 Aug 4
Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen.
2007
Antipsychotics and risk of venous thromboembolism: A population-based case-control study.
2009 Aug 9
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Beyond the dopamine receptor: novel therapeutic targets for treating schizophrenia.
2010
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
Analysis of risperidone and its metabolite in plasma and saliva by LC with coulometric detection and a novel MEPS procedure.
2010 Jun 15
Gene expression of NMDA receptor subunits in the cerebellum of elderly patients with schizophrenia.
2010 Mar
Patents

Patents

Sample Use Guides

Initial Dose 20 mg (1/2 tablet), Average dosage 40-120 mg (1-3 tablets)
Route of Administration: Oral
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.
Name Type Language
PIPAMPERONE HYDROCHLORIDE
JAN   MART.   WHO-DD  
Common Name English
PIPAMPERONE 2HCL
Common Name English
NSC-170981
Code English
PIPAMPERONE DIHYDROCHLORIDE
MI  
Common Name English
PIPAMPERONE HYDROCHLORIDE [JAN]
Common Name English
DIPIPERON
Brand Name English
Pipamperone hydrochloride [WHO-DD]
Common Name English
PIPAMPERONE DIHYDROCHLORIDE [MI]
Common Name English
1'-(3-(P-FLUOROBENZOYL)PROPYL)-(1,4'-BIPIPERIDINE)-4'-CARBOXAMIDE DIHYDROCHLORIDE
Common Name English
PIPAMPERONE HYDROCHLORIDE [MART.]
Common Name English
Code System Code Type Description
SMS_ID
100000085607
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL440294
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID6046505
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
219-507-5
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
CHEBI
32004
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
EVMPD
SUB03835MIG
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
PUBCHEM
17139
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
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CAS
2448-68-2
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
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DRUG BANK
DBSALT001283
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
MERCK INDEX
m8838
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY Merck Index
RXCUI
289159
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY RxNorm
FDA UNII
IT085U64JB
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY
NSC
170981
Created by admin on Fri Dec 15 18:37:59 GMT 2023 , Edited by admin on Fri Dec 15 18:37:59 GMT 2023
PRIMARY