U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
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
[Models of drug treatment in the attention deficit disorder with hyperactivity].
2002 Feb
[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
Hypothermia following antipsychotic drug use.
2007 Jun
Antipsychotics and risk of venous thromboembolism: A population-based case-control study.
2009 Aug 9
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
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
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 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
WHO-VATC QN05AD05
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
Code System Code Type Description
DRUG CENTRAL
2181
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
PRIMARY
CAS
1893-33-0
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
PRIMARY
INN
1588
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PRIMARY
ChEMBL
CHEMBL440294
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EPA CompTox
DTXSID8048369
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PRIMARY
MESH
C005569
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PRIMARY
MERCK INDEX
m8838
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PRIMARY Merck Index
PUBCHEM
4830
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PRIMARY
SMS_ID
100000081961
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PRIMARY
RXCUI
33739
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB09286
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PRIMARY
FDA UNII
5402501F0W
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PRIMARY
CHEBI
78549
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PRIMARY
NSC
759178
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
PRIMARY
WIKIPEDIA
PIPAMPERONE
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
PRIMARY
EVMPD
SUB09860MIG
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
PRIMARY
NCI_THESAURUS
C73297
Created by admin on Fri Dec 15 15:10:30 GMT 2023 , Edited by admin on Fri Dec 15 15:10:30 GMT 2023
PRIMARY