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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
Structure of PIPAMPERONE

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)

HIDE SMILES / InChI

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

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
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
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
Antipsychotic-induced extrapyramidal syndromes. Risperidone compared with low- and high-potency conventional antipsychotic drugs.
2001 Jul
Pharmacokinetics of pipamperone from three different tablet formulations.
2002
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.
2002 Apr
[Models of drug treatment in the attention deficit disorder with hyperactivity].
2002 Feb
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
Role of 5-HT(2) receptors in the tryptamine-induced 5-HT syndrome in rats.
2002 Jul
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
Stability indicating LC method for the determination of pipamperone.
2005 Oct 4
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
Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor.
2006 Dec 3
[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
Management of a severe forceful breather with Rett syndrome using carbogen.
2006 Nov
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
Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen.
2007
Hypothermia following antipsychotic drug use.
2007 Jun
[Enuresis in therapy with psychotropic drugs].
2007 Sep 5
[Pipamperone and the treatment of impulsive aggressive behaviour].
2008
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
Validation of a solid-phase extraction and liquid chromatography-electrospray tandem mass spectrometric method for the determination of nine basic pharmaceuticals in wastewater and surface water samples.
2008 Feb 29
[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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:10:30 UTC 2023
Edited
by admin
on Fri Dec 15 15:10:30 UTC 2023
Record UNII
5402501F0W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPAMPERONE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
PIPAMPERONE [USAN]
Common Name English
PIPAMPERONE [MART.]
Common Name English
R-3345
Code English
PIPAMPERONE [MI]
Common Name English
pipamperone [INN]
Common Name English
NSC-759178
Code English
R 3345
Code English
Pipamperone [WHO-DD]
Common Name English
1'-(3-(P-FLUOROBENZOYL)PROPYL)-(1,4'-BIPIPERIDINE)-4'-CARBOXAMIDE
Common Name English
(1,4'-BIPIPERIDINE)-4'-CARBOXAMIDE, 1'-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)-
Systematic Name English
Classification Tree Code System Code
WHO-ATC N05AD05
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
WHO-VATC QN05AD05
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2181
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
CAS
1893-33-0
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
INN
1588
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
ChEMBL
CHEMBL440294
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID8048369
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
MESH
C005569
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
MERCK INDEX
m8838
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY Merck Index
PUBCHEM
4830
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
SMS_ID
100000081961
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
RXCUI
33739
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB09286
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
FDA UNII
5402501F0W
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
CHEBI
78549
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
NSC
759178
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
WIKIPEDIA
PIPAMPERONE
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
EVMPD
SUB09860MIG
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
NCI_THESAURUS
C73297
Created by admin on Fri Dec 15 15:10:30 UTC 2023 , Edited by admin on Fri Dec 15 15:10:30 UTC 2023
PRIMARY
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