Compound Detail

CHEMBL936

DIPHENIDOL

💊 Approved Drug

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💊 Approved Drug

OC(CCCN1CCCCC1)(c1ccccc1)c1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL936
Name	DIPHENIDOL
Phase	Approved
Structure Type	MOL
InChI Key	OGAKLTJNUQRZJU-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Difenidol Difenidol hydrochloride Diphenidol SK&F 478 SK&F-478 SK-478 Vontrol

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

309.4

MW (Da)

4.19

ALogP

HBA

HBD

23.5

PSA (Å²)

0.86

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1967
Availability	Discontinued
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Year

1963

Extended Properties

Molecular Formula	C21H27NO
MW	309.45
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	-0.59

Activity Summary

IC50 13 meas. best 6.61

Ki 11 meas. best 7.42

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.42	7.42	38.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	7.28	7.28	52.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	7.11	7.11	78.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.97	6.97	108.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	6.61	6.61	245.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	6.59	6.59	256.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	6.57	6.57	271.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.56	6.56	274.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.49	6.49	326.3	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	6.49	6.49	324.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.13	6.13	739.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.11	6.11	785.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	6.11	6.11	770.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	6.07	6.07	855.0	1
D(2) dopamine receptor CHEMBL217	Ki	5.96	5.96	1097.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	5.92	5.92	1191.0	1
D(3) dopamine receptor CHEMBL234	IC50	5.64	5.64	2311.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.59	5.59	2586.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	5.58	5.58	2635.0	1
D(2) dopamine receptor CHEMBL217	IC50	5.48	5.48	3290.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	5.47	5.47	3400.0	1
Unchecked CHEMBL612545	Ki	5.36	5.36	4376.0	1
Unchecked CHEMBL612545	IC50	5.35	5.35	4501.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	5.32	5.32	4760.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Muscarinic acetylcholine receptor M4	Ki	=	38.0	nM	7.42	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M3	Ki	=	52.0	nM	7.28	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M1	Ki	=	78.0	nM	7.11	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Sigma non-opioid intracellular receptor 1	Ki	=	108.0	nM	6.97	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Muscarinic acetylcholine receptor M3	IC50	=	245.0	nM	6.61	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Sigma non-opioid intracellular receptor 1	IC50	=	256.0	nM	6.59	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Muscarinic acetylcholine receptor M4	IC50	=	271.0	nM	6.57	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M2	Ki	=	274.0	nM	6.56	DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M1	IC50	=	324.0	nM	6.49	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Cytochrome P450 2D6	IC50	=	326.3	nM	6.49	DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	-
5-hydroxytryptamine receptor 2A	Ki	=	739.0	nM	6.13	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M2	IC50	=	770.0	nM	6.11	DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
D(3) dopamine receptor	Ki	=	785.0	nM	6.11	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
Muscarinic acetylcholine receptor M5	Ki	=	855.0	nM	6.07	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
D(2) dopamine receptor	Ki	=	1097.0	nM	5.96	DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone)	-
Muscarinic acetylcholine receptor M5	IC50	=	1191.0	nM	5.92	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
D(3) dopamine receptor	IC50	=	2311.0	nM	5.64	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
5-hydroxytryptamine receptor 2A	IC50	=	2586.0	nM	5.59	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Alpha-1B adrenergic receptor	Ki	=	2635.0	nM	5.58	DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin)	-
D(2) dopamine receptor	IC50	=	3290.0	nM	5.48	DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone)	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	332
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	2
37468498	10.1038/s41467-023-40064-9	Thromboxane A2 receptor	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	2
2579237	10.1021/jm00381a019	Sodium channel alpha subunits; brain (Types I, II, III)	2
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	2
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	2
37468498	10.1038/s41467-023-40064-9	Sodium-dependent dopamine transporter	1
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	1
37468498	10.1038/s41467-023-40064-9	Amine oxidase [flavin-containing] A	1
38318365	10.1016/j.isci.2024.108907	Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	1
37468498	10.1038/s41467-023-40064-9	Sodium-dependent noradrenaline transporter	1
37468498	10.1038/s41467-023-40064-9	Acetylcholinesterase	1
37468498	10.1038/s41467-023-40064-9	Estrogen receptor	1
37468498	10.1038/s41467-023-40064-9	D(1A) dopamine receptor	1
24332655	10.1016/j.bmc.2013.11.049	Unchecked	1

Data from ChEMBL 36 via Core Engine