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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dipiperon
Primary
Dipiperon

Cmax

ValueDoseCo-administeredAnalytePopulation
266 ng/mL
120 mg single, oral
PIPAMPERONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3107 ng × h/mL
120 mg single, oral
PIPAMPERONE plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Initial Dose 20 mg (1/2 tablet), Average dosage 40-120 mg (1-3 tablets)
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
5402501F0W
Record Status Validated (UNII)
Record Version