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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

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

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
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
Role of 5-HT(2) receptors in the tryptamine-induced 5-HT syndrome in rats.
2002 Jul
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
[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
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
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
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 18:37:58 GMT 2023
Edited
by admin
on Fri Dec 15 18:37:58 GMT 2023
Record UNII
IT085U64JB
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
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ACTIVE MOIETY