Pipamperone

drug

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Also known as FloropipamideNSC-759178PipamperonaPipamperone hydrochloridePipaneperoneR 3345R-3345SID29217622SID50111712

Summary

Pipamperone (CHEMBL440294) is a phase-3 clinical-stage small-molecule first generation antipsychotic (ATC N05AD05) targeting HTR1A, HRH1, and HTR1B; indicated across 7 conditions including psychotic disorder and anxiety.

At a glance

Status: Max clinical phase 3 (not approved)
Modality: Small molecule
ATC class: N05AD05
Targets: 5 (HTR1A, HRH1, HTR1B…)
Indications: 7 conditions
Clinical trials: 4
Chemistry: 375.5 Da · C21H30FN3O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL440294
Name	Pipamperone
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	4830
ChEBI	CHEBI:78549
ATC	N05AD05
Molecular formula	C21H30FN3O2
Molecular weight	375.5
InChIKey	AXKPFOAXAHJUAG-UHFFFAOYSA-N

SMILES: C1CCN(CC1)C2(CCN(CC2)CCCC(=O)C3=CC=C(C=C3)F)C(=O)N

IUPAC name: 1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide

ChEBI definition: A member of the class of bipiperidines that is 1,4’-bipiperidine which is substituted at the 1’ and 4’ positions by 4-(p-fluorophenyl)-4-oxobutyl and carboxamide groups, respectively. A first generation antipsychotic, its properties are generally similar to those of haloperidol.

Pharmacological roles (ChEBI): first generation antipsychotic, serotonergic antagonist, dopaminergic antagonist.

Also known as: Floropipamide, NSC-759178, Pipamperona, Pipamperone, Pipamperone hydrochloride, Pipaneperone, R 3345, R-3345, SID29217622, SID50111712, PIPAMPERONE, pipamperone

Parent form; salt/anhydrous children: CHEMBL2361301

Patent coverage: 4,570 distinct patent families (15,661 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
HTR1A	5-HT_1A receptor	Antagonist	5.6	0%	P08908
HRH1	H₁ receptor	Antagonist	5.6	0%	P35367
HTR1B	5-HT_1B receptor	Antagonist	6.2	0.2%	P28222
HTR1D	5-HT_1D receptor	Antagonist	6.8	0%	P28221
HTR2A	5-HT_2A receptor	Antagonist	8.3	0%	P28223

Broader ChEMBL bioactivity targets: 10 (assay-derived). Sample: Alpha-2A adrenergic receptor, D(1A) dopamine receptor, 5-hydroxytryptamine receptor 1A, Sodium-dependent serotonin transporter, Alpha-1A adrenergic receptor, Mu-type opioid receptor, D(3) dopamine receptor, Sodium-dependent dopamine transporter, Voltage-gated inwardly rectifying potassium channel KCNH2, Histamine H3 receptor.

Bioactivity

ChEMBL activities: 7 potent at pChembl ≥ 5 of 10 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
DRD1	6.59	AC50	257.6	nM	CHEMBL_ACT_25115078
ADRA1A	6.4	AC50	397.5	nM	CHEMBL_ACT_25218739
DRD3	5.75	AC50	1768	nM	CHEMBL_ACT_25194393
KCNH2	5.72	AC50	1900	nM	CHEMBL_ACT_25117396
SLC6A3	5.53	AC50	2921	nM	CHEMBL_ACT_25124827
ADRA2A	5.26	AC50	5470	nM	CHEMBL_ACT_25156297
OPRM1	5.15	AC50	7021	nM	CHEMBL_ACT_25158043

Target pathways

Aggregated over 5 target gene(s): HTR1A, HRH1, HTR1B, HTR1D, HTR2A.

Top Reactome pathways

10 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	4	HTR1A, HTR1B, HTR1D, HTR2A
Signaling by GPCR	4	HTR1A, HTR1B, HTR1D, HTR2A
Class A/1 (Rhodopsin-like receptors)	4	HTR1A, HTR1B, HTR1D, HTR2A
Amine ligand-binding receptors	4	HTR1A, HTR1B, HTR1D, HTR2A
Serotonin receptors	4	HTR1A, HTR1B, HTR1D, HTR2A
GPCR ligand binding	4	HTR1A, HTR1B, HTR1D, HTR2A
GPCR downstream signalling	3	HTR1B, HTR1D, HTR2A
G alpha (q) signalling events	2	HRH1, HTR2A
G alpha (i) signalling events	2	HTR1B, HTR1D
Histamine receptors	1	HRH1

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway	5
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	5
chemical synaptic transmission	5
signal transduction	5
adenylate cyclase-inhibiting serotonin receptor signaling pathway	3
regulation of behavior	3
phospholipase C-activating serotonin receptor signaling pathway	3
serotonin receptor signaling pathway	2
positive regulation of cell population proliferation	2
adenylate cyclase-activating G protein-coupled receptor signaling pathway	2
G protein-coupled serotonin receptor signaling pathway	2
memory	2
positive regulation of vasoconstriction	2
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	2
vasoconstriction	2

Indications & clinical

Indications

7 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
psychotic disorder	3	MONDO:0005485	EFO:0005407
anxiety	3	MONDO:0011918	EFO:0005230
schizoaffective disorder	3	MONDO:0005487	EFO:0005411
dementia	3	MONDO:0001627	HP:0000726
major depressive disorder	3	MONDO:0002009	MONDO:0002009
depressive disorder	3	MONDO:0002050	MONDO:0002050

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 4.

Phase distribution

Phase	Trials
PHASE3	2
PHASE2	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01312922	PHASE3	COMPLETED	Pipamperone/Citalopram (PNB01) Versus Citalopram (CIT) and Versus Pipamperone (PIP) in Major Depressive Disorder (MDD)
NCT02374567	PHASE3	TERMINATED	Pharmacovigilance in Gerontopsychiatric Patients
NCT00672659	PHASE2	COMPLETED	Pipamperone/Citalopram (PipCit)Versus Citalopram in the Treatment of Major Depressive Disorder(MDD)
NCT01450514	PHASE2	COMPLETED	POC Study of Pipamperone Added to Stable Treatment With RIS or PAL in Chronic Schizophrenia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

674 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
DIHYDROERGOTAMINE	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
CARIPRAZINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
IMIPRAMINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
KETANSERIN	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
NEFAZODONE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
RISPERIDONE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
RIZATRIPTAN	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D, HTR2A
PALIPERIDONE	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1B, HTR1D, HTR2A
PRAMIPEXOLE	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR2A
AZELASTINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1B, HTR1D, HTR2A
CINACALCET	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1D, HTR2A
CLOZAPINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR2A
ERGOTAMINE	ChEMBL	Phase 4 (approved)	HTR1A, HTR1B, HTR1D, HTR2A
MIANSERIN	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1D, HTR2A
OLANZAPINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR2A
OXYMETAZOLINE	ChEMBL	Phase 4 (approved)	HTR1A, HTR1B, HTR1D, HTR2A
SALMETEROL	ChEMBL	Phase 4 (approved)	HTR1A, HTR1B, HTR1D, HTR2A
SERTINDOLE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR2A
SILODOSIN	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D
SUMATRIPTAN	ChEMBL	Phase 4 (approved)	HTR1A, HTR1B, HTR1D, HTR2A
VILAZODONE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR1B, HTR1D
XYLOMETAZOLINE	ChEMBL	Phase 4 (approved)	HTR1A, HTR1B, HTR1D, HTR2A
ZOLMITRIPTAN	ChEMBL	Phase 4 (approved)	HTR1A, HTR1B, HTR1D, HTR2A
SEROTONIN	ChEMBL	Phase 3	HTR1A, HTR1B, HTR1D, HTR2A
YOHIMBINE	ChEMBL	Phase 3	HTR1A, HTR1B, HTR1D, HTR2A
GSK163090	ChEMBL	Phase 2	HTR1A, HTR1B, HTR1D, HTR2A
LYSERGIDE	ChEMBL	Phase 2	HRH1, HTR1A, HTR1D, HTR2A
MEBUFOTENIN	ChEMBL	Phase 2	HTR1A, HTR1B, HTR1D, HTR2A
PENFLURIDOL	ChEMBL	Phase 2	HRH1, HTR1A, HTR1D, HTR2A
PSILOCIN	ChEMBL	Phase 2	HTR1A, HTR1B, HTR1D, HTR2A
RITANSERIN	ChEMBL	Phase 2	HRH1, HTR1A, HTR1B, HTR2A
SPIRAMIDE	ChEMBL	Phase 2	HRH1, HTR1A, HTR1D, HTR2A
ALMOTRIPTAN	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR2A
DESLORATADINE	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR2A
Fidaxomicin	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR2A
OLODATEROL	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR2A
Propoxyphene	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR2A
REGORAFENIB	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR2A
TAMSULOSIN	ChEMBL + PubChem	Phase 4 (approved)	HRH1, HTR1A, HTR2A
ACETOPHENAZINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
AMOXAPINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
APOMORPHINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
ASENAPINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
AZATADINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
BENFLUOREX	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
BENPERIDOL	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
BROMPERIDOL	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
BUSPIRONE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CABERGOLINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CANDESARTAN CILEXETIL	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CINNARIZINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CISAPRIDE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CITALOPRAM	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CLEMASTINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	HRH1, HTR1A, HTR2A

Genes: HTR1A, HRH1, HTR1B, HTR1D, HTR2A
Diseases: psychotic disorder, anxiety, schizoaffective disorder, dementia, major depressive disorder, depressive disorder
Drugs: Dihydroergotamine, Aripiprazole, Brexpiprazole, Cariprazine, Imipramine, Ketanserin, Nefazodone, Risperidone, Rizatriptan, Paliperidone, Pramipexole, Azelastine, Cinacalcet, Clozapine, Ergotamine, Mianserin, Olanzapine, Oxymetazoline, Salmeterol, Sertindole, Silodosin, Sumatriptan, Vilazodone, Xylometazoline, Zolmitriptan, Serotonin, Yohimbine, Almotriptan, Desloratadine, Fidaxomicin, Olodaterol, Propoxyphene, Regorafenib, Tamsulosin, Acetophenazine, Amitriptyline, Amoxapine, Apomorphine, Asenapine, Astemizole, Azatadine, Benfluorex, Benperidol, Bromperidol, Buspirone, Cabergoline, Candesartan Cilexetil, Chlorpromazine, Cinnarizine, Cisapride, Citalopram, Clemastine, Clomipramine

Summary

Identifiers

Drug identity and classification

Targets

Targets

Bioactivity

Target pathways

Top Reactome pathways

Dominant GO biological processes

Indications & clinical

Indications

Clinical trials

Phase distribution

Top trials by phase / activity

Clinical evidence (CIViC)

Pharmacology

Pharmacogenomics

Related molecules

Related molecules

Related Atlas pages