Compound Detail

CHEMBL567

PERPHENAZINE

💊 Approved Drug

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💊 Approved Drug

OCCN1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc32)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL567
Name	PERPHENAZINE
Phase	Approved
Structure Type	MOL
InChI Key	RGCVKNLCSQQDEP-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Chlorpiprazine Decentan Fentazin NSC-150866 Perfenazina Perphenazine Perphenazine component of etrafon-a Perphenazine maleate Trilafon Trilafon-la

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

404.0

MW (Da)

3.94

ALogP

HBA

HBD

29.9

PSA (Å²)

0.79

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1957
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula	C21H26ClN3OS
MW	403.98
Aromatic Rings	2
Heavy Atoms	27
NP-Likeness	-1.27

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Dopamine D2 receptor antagonist	ANTAGONIST	D(2) dopamine receptor	✓	✓

Indications

Postoperative Nausea and Vomiting Psychotic Disorders Schizophrenia Anxiety Dementia Depressive Disorder Psychomotor Agitation Cocaine-Related Disorders Ischemic Stroke

ATC Classification

N05AB03

perphenazine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning

psychiatric toxicity

Country: United States

Black Box Warning

General Warning

Country: United States

Activity Summary

IC50 53 meas. best 9.52

EC50 6 meas. best 5.3

Ki 2 meas. best 7.64

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
D(2) dopamine receptor CHEMBL217	IC50	9.52	9.52	0.3	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.64	7.64	23.0	1
Aldehyde oxidase CHEMBL3257	IC50	7.48	7.48	33.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.92	6.92	120.0	1
Aldehyde dehydrogenase 1A1 CHEMBL3577	IC50	6.28	6.28	524.2	1
Aldehyde oxidase 1 CHEMBL1641355	IC50	6.13	6.13	740.0	1
Pleiotropic ABC efflux transporter of multiple drugs CHEMBL1697658	IC50	5.85	5.85	1400.0	1
Plasmodium falciparum CHEMBL364	IC50	5.6	5.3857	2511.9	7
Alpha-2A adrenergic receptor CHEMBL1867	IC50	5.56	5.56	2774.5	1
Beta-2 adrenergic receptor CHEMBL210	IC50	5.56	5.56	2777.1	1
CX3C chemokine receptor 1 CHEMBL4843	IC50	5.53	5.53	2949.1	1
Apelin receptor CHEMBL1628481	IC50	5.49	5.49	3217.7	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	5.46	5.46	3454.1	1
Aldehyde oxidase 1 CHEMBL1641357	IC50	5.44	5.44	3600.0	1
Glucagon-like peptide 1 receptor CHEMBL1784	IC50	5.41	5.41	3931.1	1
Psychosine receptor CHEMBL3714081	IC50	5.4	5.4	3943.7	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.38	5.38	4216.0	1
G-protein coupled receptor 183 CHEMBL3259470	IC50	5.38	5.38	4172.2	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.35	5.35	4490.0	1
fMet-Leu-Phe receptor CHEMBL3359	IC50	5.32	5.32	4803.4	1
Unchecked CHEMBL612545	IC50	5.32	4.7771	4800.0	7
Trypanosoma cruzi CHEMBL368	EC50	5.3	5.3	5000.0	1
Glucose-dependent insulinotropic receptor CHEMBL5652	IC50	5.29	5.29	5164.6	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	5.22	5.22	5966.8	1
N-formyl peptide receptor 3 CHEMBL5646	IC50	5.21	5.21	6242.6	1
Aldehyde oxidase 1 CHEMBL1641354	IC50	5.21	5.21	6100.0	1
Unchecked CHEMBL612545	EC50	4.98	4.9533	10420.0	3
Cytochrome P450 2J2 CHEMBL3491	IC50	4.97	4.97	10600.0	1
ADMET CHEMBL612558	EC50	4.89	4.89	13000.0	1
Ubiquitin-conjugating enzyme E2 N CHEMBL6089	IC50	4.87	4.83	13424.0	2
Cytochrome P450 3A4 CHEMBL340	IC50	4.86	4.86	13900.0	1
HepG2 CHEMBL395	IC50	4.79	4.79	16218.1	1
Cytochrome P450 2C19 CHEMBL3622	IC50	4.73	4.73	18500.0	1
Ishikawa CHEMBL614649	IC50	4.71	4.71	19400.0	1
Cytochrome P450 2C9 CHEMBL3397	IC50	4.67	4.67	21300.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.64	4.64	23120.0	1
HEC-1-A CHEMBL4296424	IC50	4.63	4.63	23300.0	1
Chikungunya virus CHEMBL4296563	IC50	4.6	4.6	25100.0	1
AN3-CA CHEMBL1075392	IC50	4.59	4.59	25400.0	1
HEC-1B cell line CHEMBL614817	IC50	4.53	4.53	29800.0	1
MDA-MB-231 CHEMBL400	IC50	4.52	4.51	30370.0	2
KLE CHEMBL2366239	IC50	4.51	4.51	30800.0	1
Bile salt export pump CHEMBL6020	IC50	4.46	4.46	34840.0	1
MCF7 CHEMBL387	IC50	4.45	4.45	35810.0	1
HUVEC CHEMBL613979	IC50	4.01	4.01	97760.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	27.0	mL.min-1.kg-1	Homo sapiens
CL	27.0	mL.min-1.kg-1	Homo sapiens
F	79.0	%	Homo sapiens
Fu	0.07	-	Homo sapiens
Fu	0.004	-	Rattus norvegicus
Fu	0.07	-	Homo sapiens
MRT	11.0	hr	Homo sapiens
T1/2	9.4	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(2) dopamine receptor	IC50	=	0.3	nM	9.52	Antagonist activity at dopamine D2 receptor (unknown origin) expressed in CHOK1 ...	23675993
5-hydroxytryptamine receptor 7	Ki	=	23.0	nM	7.64	Binding affinity towards human 5-hydroxytryptamine 7 receptor	12825922
Aldehyde oxidase	IC50	=	33.0	nM	7.48	Inhibition of human aldehyde oxidase	20853847
Cytochrome P450 2D6	IC50	=	120.0	nM	6.92	Inhibition of CYP2D6 in human liver microsomes using bufuralol substrate by LC-M...	23033255
Aldehyde dehydrogenase 1A1	IC50	=	524.21	nM	6.28	Inhibition of ALDH1A1 in human drug-tolerant MDA-MB-231/lapatinib cells assessed...	34435487
Aldehyde oxidase 1	IC50	=	740.0	nM	6.13	Inhibition of rat aldehyde oxidase	20853847
Pleiotropic ABC efflux transporter of multiple drugs	IC50	=	1400.0	nM	5.85	Inhibition of Pdr5p-mediated rhodamine 6G transport in Saccharomyces cerevisiae ...	19188399
Plasmodium falciparum	IC50	=	2511.89	nM	5.6	Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	2511.89	nM	5.6	Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr...	19734910
Alpha-2A adrenergic receptor	IC50	=	2774.51	nM	5.56	GPCR PRESTO-Tango dose-response in antagonist mode with target: ADRA2A	-
Beta-2 adrenergic receptor	IC50	=	2777.1	nM	5.56	GPCR PRESTO-Tango dose-response in antagonist mode with target: ADRB2	-
CX3C chemokine receptor 1	IC50	=	2949.1	nM	5.53	GPCR PRESTO-Tango dose-response in antagonist mode with target: CX3CR1	-
Plasmodium falciparum	IC50	=	3162.28	nM	5.5	Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g...	19734910
Apelin receptor	IC50	=	3217.72	nM	5.49	GPCR PRESTO-Tango dose-response in antagonist mode with target: APLNR	-
Voltage-gated inwardly rectifying potassium channel KCNH2	Ki	=	3454.1	nM	5.46	DRUGMATRIX: Potassium Channel HERG radioligand binding (ligand: [3H] Astemizole)	-
Aldehyde oxidase 1	IC50	=	3600.0	nM	5.44	Inhibition of monkey aldehyde oxidase	20853847
Glucagon-like peptide 1 receptor	IC50	=	3931.05	nM	5.41	GPCR PRESTO-Tango dose-response in antagonist mode with target: GLP1R	-
Plasmodium falciparum	IC50	=	3981.07	nM	5.4	Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	3981.07	nM	5.4	Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g...	19734910
Psychosine receptor	IC50	=	3943.65	nM	5.4	GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR65	-

Literature References

PubMed	DOI	Target Context	# Activities
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
32527541	10.1016/j.bmcl.2020.127239	Ishikawa	13
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
32527541	10.1016/j.bmcl.2020.127239	KLE	11
-	10.6019/CHEMBL5058564	HEK-293T	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
-	10.6019/CHEMBL5058564	Fibroblast	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
-	10.6019/CHEMBL5058564	U2OS	6
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
18363346	10.1021/jm7012453	Rattus norvegicus	5
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	5
-	10.6019/CHEMBL5209801	Apelin receptor	5
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	5
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	5
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	5
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5

Data from ChEMBL 36 via Core Engine