Compound Detail

CHEMBL534

KETOTIFEN

💊 Approved Drug

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💊 Approved Drug

CN1CCC(=C2c3ccccc3CC(=O)c3sccc32)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL534
Name	KETOTIFEN
Phase	Approved
Structure Type	MOL
InChI Key	ZCVMWBYGMWKGHF-UHFFFAOYSA-N
Therapeutic	✓ Yes
Active Moiety	CHEMBL1197564

Known Names

(r)-ketotifen Ketotifen Ketotifene Ketotifeno

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

309.4

MW (Da)

4.01

ALogP

HBA

HBD

20.3

PSA (Å²)

0.73

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1999
Availability	OTC
Chirality	Achiral

Routes of Administration

Topical

Flags

Natural Product Prodrug

USAN Year

1979

Extended Properties

Molecular Formula	C19H19NOS
MW	309.43
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	-0.01

Indications

Eye Manifestations Hypersensitivity Conjunctivitis, Allergic Dyspepsia Fibromyalgia Peripheral Nervous System Diseases Rhinitis, Allergic, Perennial Severe Acute Respiratory Syndrome Contracture Peanut Hypersensitivity

ATC Classification

R06AX17

ketotifen

Level 1: RESPIRATORY SYSTEM

Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

S01GX08

ketotifen

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 34 meas. best 9.0

Ki 24 meas. best 9.86

Kd 2 meas. best 9.5

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histamine H1 receptor CHEMBL231	Ki	9.86	9.83	0.1	2
Histamine H1 receptor CHEMBL3943	Ki	9.51	9.51	0.3	1
Histamine H1 receptor CHEMBL3943	Kd	9.5	9.5	0.3	2
Histamine H1 receptor CHEMBL231	IC50	9.0	7.3025	1.0	4
Cavia porcellus CHEMBL369	IC50	8.8	8.495	1.6	2
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	8.05	7.925	9.0	2
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.54	7.52	29.0	2
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	7.51	7.51	31.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	7.34	7.34	46.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	7.08	6.89	84.0	2
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	6.85	6.85	141.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.8	6.8	160.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	6.57	6.57	269.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.57	6.57	268.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.53	6.53	298.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.49	6.49	324.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	6.43	6.43	374.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.36	6.36	436.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	6.33	6.33	468.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.28	6.28	530.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.18	6.18	667.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.15	6.15	710.0	1
Plasmodium falciparum CHEMBL364	IC50	6.12	6.12	750.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.09	6.09	820.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	6.08	6.08	838.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	6.06	6.06	872.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	6.0	6.0	1009.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	5.95	5.95	1112.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	5.94	5.94	1141.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	5.84	5.84	1450.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	5.74	5.74	1832.0	1
D(3) dopamine receptor CHEMBL234	IC50	5.71	5.71	1963.0	1
Unchecked CHEMBL612545	Ki	5.69	5.69	2049.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	5.66	5.66	2187.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	5.66	5.66	2209.0	1
Unchecked CHEMBL612545	IC50	5.64	5.64	2305.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	5.6	5.6	2537.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	5.43	5.43	3727.0	1
Histamine H2 receptor CHEMBL1941	Ki	5.39	5.39	4060.0	1
Histamine H2 receptor CHEMBL1941	IC50	5.38	5.38	4129.0	1
Rattus norvegicus CHEMBL376	IC50	5.04	4.9067	9100.0	3
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	4.82	4.82	15190.0	1
Histamine H4 receptor CHEMBL3759	IC50	4.68	4.68	21000.0	1
Histamine H4 receptor CHEMBL3759	Ki	4.68	4.68	21000.0	1
RBL-2H3 CHEMBL614632	IC50	4.55	4.5	27900.0	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histamine H1 receptor	Ki	=	0.138	nM	9.86	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Histamine H1 receptor	Ki	=	0.1585	nM	9.8	Antagonist activity against human histamine H1 receptor expressed in CHO cells b...	20942472
Histamine H1 receptor	Ki	=	0.31	nM	9.51	The compound was tested in vitro for binding affinity against histamine H1 recep...	1350797
Histamine H1 receptor	Kd	=	0.3162	nM	9.5	H1-antihistamine activity on guinea pig ileum	6208360
Histamine H1 receptor	Kd	=	0.3162	nM	9.5	H1-antihistamine activity in guinea pig ileum	2431143
Histamine H1 receptor	IC50	=	1.0	nM	9.0	Displacement of [3H]pyrilamine from human histamine H1 receptor expressed in CHO...	21470866
Histamine H1 receptor	IC50	=	1.188	nM	8.93	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Cavia porcellus	IC50	=	1.6	nM	8.8	Anti-histaminic activity was measured in guinea pig trachea	2465410
Cavia porcellus	IC50	=	6.4	nM	8.19	Ability to inhibit histamine-induced contractions of isolated guinea pig ileum	7861415
5-hydroxytryptamine receptor 2A	Ki	=	8.977	nM	8.05	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2A	Ki	=	15.85	nM	7.8	Antagonist activity at human 5HT2A receptor expressed in HEK cells assessed as i...	20942472
5-hydroxytryptamine receptor 2B	Ki	=	29.0	nM	7.54	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2A	IC50	=	31.0	nM	7.51	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2B	Ki	=	31.62	nM	7.5	Antagonist activity at human 5HT2B receptor expressed in human SH-SY5Y cells by ...	20942472
5-hydroxytryptamine receptor 2B	IC50	=	46.0	nM	7.34	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2C	Ki	=	84.0	nM	7.08	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M4	Ki	=	141.0	nM	6.85	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
5-hydroxytryptamine receptor 2C	IC50	=	160.0	nM	6.8	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2C	Ki	=	199.53	nM	6.7	Antagonist activity at human 5HT2C receptor expressed in human SH-SY5Y cells by ...	20942472
Muscarinic acetylcholine receptor M5	Ki	=	269.0	nM	6.57	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	65
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
2872333	10.1021/jm00156a034	Cavia porcellus	10
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
2872333	10.1021/jm00156a034	Rattus norvegicus	8
3612683	10.1021/jm00391a010	Cavia porcellus	5
15781124	10.1016/j.pharmthera.2004.10.013	UDP-glucuronosyltransferase 1A4	4
15781124	10.1016/j.pharmthera.2004.10.013	UDP-glucuronosyltransferase 1A3	4
3612683	10.1021/jm00391a010	Homo sapiens	4
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	3
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	3
21470866	10.1016/j.bmc.2011.03.003	Mus musculus	3
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	3
7861415	10.1021/jm00004a013	Cavia porcellus	3
2879915	10.1021/jm00384a002	Rattus norvegicus	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2A	3
7861415	10.1021/jm00004a013	Rattus norvegicus	2

Data from ChEMBL 36 via Core Engine