Compound Detail

CHEMBL1200406

DIMENHYDRINATE

💊 Approved Drug

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💊 Approved Drug

CN(C)CCOC(c1ccccc1)c1ccccc1.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1200406
Name	DIMENHYDRINATE
Phase	Approved
Structure Type	MOL
InChI Key	NFLLKCVHYJRNRH-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Antemin Dimenhidrinato Dimenhydrinate Dramamine NSC-117855 Vertigo-vomex s

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

470.0

MW (Da)

Drug Information

Molecule Type	Small molecule
First Approval	1972
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Extended Properties

Molecular Formula	C24H28ClN5O3
MW	469.97

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Histamine H1 receptor antagonist	ANTAGONIST	Histamine H1 receptor	✓	✓

Indications

Hypersensitivity Vertigo Postoperative Nausea and Vomiting

ATC Classification

R06AA11

dimenhydrinate

Level 1: RESPIRATORY SYSTEM

Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

IC50 17 meas. best 6.5

Ki 16 meas. best 7.43

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histamine H1 receptor CHEMBL231	Ki	7.43	7.43	37.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.1	7.1	80.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	7.02	7.02	95.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.96	6.96	109.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.79	6.79	164.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.7	6.7	198.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	6.64	6.64	227.0	1
Histamine H1 receptor CHEMBL231	IC50	6.5	6.5	319.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	6.5	6.5	316.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.48	6.48	332.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	6.35	6.35	451.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	6.35	6.35	447.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	6.34	6.34	461.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.31	6.31	487.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	6.24	6.24	570.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.2	6.2	634.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	6.16	6.16	693.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.96	5.96	1097.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	5.94	5.94	1158.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	5.85	5.85	1423.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	5.82	5.82	1509.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.79	5.79	1617.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.76	5.76	1724.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.75	5.75	1784.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.7	5.7	2020.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.69	5.69	2037.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	5.65	5.65	2245.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	5.6	5.6	2491.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	5.54	5.54	2894.0	1
Unchecked CHEMBL612545	Ki	5.49	5.49	3251.0	1
Unchecked CHEMBL612545	IC50	5.48	5.48	3344.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	5.37	5.37	4313.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	5.26	5.26	5457.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histamine H1 receptor	Ki	=	37.0	nM	7.43	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Muscarinic acetylcholine receptor M4	Ki	=	80.0	nM	7.1	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M3	Ki	=	95.0	nM	7.02	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M1	Ki	=	109.0	nM	6.96	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M2	Ki	=	164.0	nM	6.79	DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
5-hydroxytryptamine receptor 2A	Ki	=	198.0	nM	6.7	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M5	Ki	=	227.0	nM	6.64	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M5	IC50	=	316.0	nM	6.5	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Histamine H1 receptor	IC50	=	319.0	nM	6.5	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
5-hydroxytryptamine receptor 2C	Ki	=	332.0	nM	6.48	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M3	IC50	=	447.0	nM	6.35	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M1	IC50	=	451.0	nM	6.35	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M2	IC50	=	461.0	nM	6.34	DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Sigma non-opioid intracellular receptor 1	Ki	=	487.0	nM	6.31	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Muscarinic acetylcholine receptor M4	IC50	=	570.0	nM	6.24	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
5-hydroxytryptamine receptor 2C	IC50	=	634.0	nM	6.2	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2A	IC50	=	693.0	nM	6.16	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2B	Ki	=	1097.0	nM	5.96	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
Sigma non-opioid intracellular receptor 1	IC50	=	1158.0	nM	5.94	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Alpha-1D adrenergic receptor	Ki	=	1423.0	nM	5.85	DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin)	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	405
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
26948801	10.1016/j.drudis.2016.02.015	Homo sapiens	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B3	1
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B1	1
22961681	10.1124/dmd.112.047068	Bile salt export pump	1
23956101	10.1093/toxsci/kft176	Bile salt export pump	1
23956101	10.1093/toxsci/kft176	ATP-binding cassette sub-family C member 2	1
23956101	10.1093/toxsci/kft176	ATP-binding cassette sub-family C member 3	1
23956101	10.1093/toxsci/kft176	ATP-binding cassette sub-family C member 4	1
-	10.1101/2020.04.03.023846	SARS-CoV-2	1
-	10.21203/rs.3.rs-23951/v1	SARS-CoV-2	1

Data from ChEMBL 36 via Core Engine