Compound Detail

CHEMBL305660

EBASTINE

💊 Approved Drug

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💊 Approved Drug

CC(C)(C)c1ccc(C(=O)CCCN2CCC(OC(c3ccccc3)c3ccccc3)CC2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL305660
Name	EBASTINE
Phase	Approved
Structure Type	MOL
InChI Key	MJJALKDDGIKVBE-UHFFFAOYSA-N

Known Names

Ebastina Ebastine LAS W-090 LAS-W-090 RP 64305 RP-64305

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

469.7

MW (Da)

7.22

ALogP

HBA

HBD

29.5

PSA (Å²)

0.31

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1990
Availability	Unknown
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-astine
USAN Year	1987

Extended Properties

Molecular Formula	C32H39NO2
MW	469.67
Aromatic Rings	3
Heavy Atoms	35
NP-Likeness	-0.64

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Histamine H1 receptor inverse agonist	INVERSE AGONIST	Histamine H1 receptor	✓	✓

Indications

Hypersensitivity Irritable Bowel Syndrome

ATC Classification

R06AX22

ebastine

Level 1: RESPIRATORY SYSTEM

Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

IC50 48 meas. best 7.55

Ki 35 meas. best 8.48

Kd 2 meas. best 8.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histamine H1 receptor CHEMBL231	Ki	8.48	8.48	3.3	1
No relevant target CHEMBL2362975	Kd	8.4	8.4	4.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.59	7.59	25.8	1
5'-AMP-activated protein kinase catalytic subunit alpha-2 CHEMBL2116	Ki	7.58	7.58	26.0	1
Histamine H1 receptor CHEMBL231	IC50	7.55	7.55	28.3	1
Unchecked CHEMBL612545	Ki	7.44	6.906	36.0	5
ADMET CHEMBL612558	Kd	7.4	7.4	39.8	1
Unchecked CHEMBL612545	IC50	7.4	6.505	39.5	6
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.4	7.4	40.1	1
D(3) dopamine receptor CHEMBL234	Ki	7.38	7.38	41.3	1
Histamine H1 receptor CHEMBL3943	IC50	7.35	7.35	45.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	7.33	7.33	47.0	1
D(2) dopamine receptor CHEMBL217	IC50	7.21	6.575	61.0	2
Sodium-dependent dopamine transporter CHEMBL238	Ki	7.11	7.11	78.4	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	7.07	7.07	85.8	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	7.04	7.04	90.4	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	7.01	7.01	98.7	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	7.0	7.0	101.2	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.98	6.3267	104.8	3
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	6.94	6.94	115.5	1
D(3) dopamine receptor CHEMBL234	IC50	6.92	6.92	121.6	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.91	6.91	124.4	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	6.86	6.86	137.2	1
Adrenergic receptor alpha-1 CHEMBL2094251	IC50	6.74	6.74	183.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.7	6.7	198.9	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.63	6.63	232.9	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.62	6.62	237.5	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	6.62	6.62	242.7	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	6.56	6.56	275.7	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.55	6.55	279.5	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.51	6.51	311.9	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.5	6.5	312.6	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.47	6.47	337.3	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	6.47	6.47	337.8	1
D(2) dopamine receptor CHEMBL217	Ki	6.42	6.42	383.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	6.38	6.38	420.7	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	6.38	6.17	420.3	2
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	6.34	6.34	460.3	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	6.34	6.34	456.4	1
D(4) dopamine receptor CHEMBL219	Ki	6.34	6.34	455.7	1
Epidermal growth factor receptor CHEMBL203	IC50	6.25	6.25	559.1	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.22	6.22	596.5	1
Substance-K receptor CHEMBL2327	Ki	6.19	6.19	644.3	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	6.19	6.19	647.5	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.18	6.18	652.8	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.13	6.13	738.9	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	6.11	6.11	786.0	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	6.09	6.09	810.1	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	6.08	6.08	827.9	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	6.08	6.08	831.6	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histamine H1 receptor	Ki	=	3.287	nM	8.48	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
No relevant target	Kd	=	4.0	nM	8.4	Dissociation constant (KD) of the compound	7562938
5-hydroxytryptamine receptor 2A	Ki	=	25.8	nM	7.59	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5'-AMP-activated protein kinase catalytic subunit alpha-2	Ki	=	26.0	nM	7.58	Binding affinity to AMPK (unknown origin) assessed as inhibition constant	38295689
Histamine H1 receptor	IC50	=	28.3	nM	7.55	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Unchecked	Ki	=	36.0	nM	7.44	DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox...	-
Unchecked	IC50	=	39.5	nM	7.4	DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox...	-
ADMET	Kd	=	39.81	nM	7.4	pA2 value is determined compared to standard H1-antagonists	7562938
Alpha-2C adrenergic receptor	Ki	=	40.1	nM	7.4	DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912)	-
D(3) dopamine receptor	Ki	=	41.3	nM	7.38	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
Histamine H1 receptor	IC50	=	45.0	nM	7.35	Compound is evaluated for in vitro receptor binding affinity against H1 receptor	7562938
5-hydroxytryptamine receptor 1A	IC50	=	47.0	nM	7.33	Compound is evaluated for in vitro receptor binding affinity against 5-hydroxytr...	7562938
Unchecked	Ki	=	58.0	nM	7.24	DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:...	-
D(2) dopamine receptor	IC50	=	61.0	nM	7.21	Compound is evaluated for in vitro receptor binding affinity against Dopamine re...	7562938
Unchecked	IC50	=	65.3	nM	7.18	DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:...	-
Sodium-dependent dopamine transporter	Ki	=	78.4	nM	7.11	DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55)	-
Voltage-gated inwardly rectifying potassium channel KCNH2	Ki	=	85.8	nM	7.07	DRUGMATRIX: Potassium Channel HERG radioligand binding (ligand: [3H] Astemizole)	-
Unchecked	Ki	=	92.3	nM	7.04	DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:...	-
5-hydroxytryptamine receptor 2A	IC50	=	90.4	nM	7.04	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Sodium-dependent dopamine transporter	IC50	=	98.7	nM	7.01	DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55)	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	467
29624387	10.1021/acs.jmedchem.8b00035	Unchecked	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	2
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
21341745	10.1021/jm101421d	ATP-dependent translocase ABCB1	2
37468498	10.1038/s41467-023-40064-9	Beta-2 adrenergic receptor	2
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2A	2
37468498	10.1038/s41467-023-40064-9	Androgen receptor	2
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	2
37468498	10.1038/s41467-023-40064-9	Progesterone receptor	2
37468498	10.1038/s41467-023-40064-9	Beta-1 adrenergic receptor	2
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	2
7562938	10.1021/jm00020a018	Cavia porcellus	2
7562938	10.1021/jm00020a018	No relevant target	2
37468498	10.1038/s41467-023-40064-9	Gamma-aminobutyric acid receptor subunit alpha-1	2

Data from ChEMBL 36 via Core Engine