Compound Detail

CHEMBL52440

DEXTROMETHORPHAN

💊 Approved Drug

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💊 Approved Drug

COc1ccc2c(c1)[C@]13CCCC[C@@H]1[C@H](C2)N(C)CC3

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL52440
Name	DEXTROMETHORPHAN
Phase	Approved
Structure Type	MOL
InChI Key	MKXZASYAUGDDCJ-NJAFHUGGSA-N
Therapeutic	✓ Yes

Known Names

Dextromethorphan Dextromethorphane Dextrometorfano Dimetane-dx NSC-751452

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

271.4

MW (Da)

3.38

ALogP

HBA

HBD

12.5

PSA (Å²)

0.78

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1982
Availability	OTC
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-orphan
USAN Year	1987

Extended Properties

Molecular Formula	C18H25NO
MW	271.40
Aromatic Rings	1
Heavy Atoms	20
NP-Likeness	1.15

Indications

Cough Amyotrophic Lateral Sclerosis Bipolar Disorder Depressive Disorder, Treatment-Resistant Multiple Sclerosis Multiple Sclerosis, Relapsing-Remitting Opioid-Related Disorders Proteinuria Rett Syndrome Autistic Disorder Depressive Disorder, Major Diabetes Mellitus, Type 2 Diabetic Neuropathies Fibromyalgia Hypertrophy Irritable Bowel Syndrome Neuralgia Neuralgia Neurodegenerative Diseases Parkinson Disease

ATC Classification

N07XX59

dextromethorphan, combinations

Level 1: NERVOUS SYSTEM

Level 2: OTHER NERVOUS SYSTEM DRUGS

R05DA09

dextromethorphan

Level 1: RESPIRATORY SYSTEM

Level 2: COUGH AND COLD PREPARATIONS

Activity Summary

IC50 20 meas. best 8.57

Ki 9 meas. best 8.84

EC50 3 meas. best 5.49

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium-dependent serotonin transporter CHEMBL228	Ki	8.84	8.84	1.4	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	8.57	8.57	2.7	1
Sigma non-opioid intracellular receptor 1 CHEMBL4153	Ki	8.0	7.6	10.0	2
Sigma non-opioid intracellular receptor 1 CHEMBL4153	IC50	7.82	7.225	15.2	2
Cytochrome P450 2D6 CHEMBL289	IC50	7.39	6.7529	40.8	7
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.46	6.46	348.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2095171	IC50	5.89	5.89	1300.0	1
Glutamate NMDA receptor CHEMBL1907608	IC50	5.88	5.88	1320.0	1
Unchecked CHEMBL612545	Ki	5.79	5.79	1636.0	1
Glutamate [NMDA] receptor CHEMBL2094124	Ki	5.78	5.78	1680.0	1
Glutamate NMDA receptor CHEMBL1907608	Ki	5.65	5.495	2246.0	2
Unchecked CHEMBL612545	IC50	5.62	5.62	2415.0	1
Mas-related G-protein coupled receptor member X2 CHEMBL5849	EC50	5.49	5.36	3235.9	2
Sigma non-opioid intracellular receptor 1 CHEMBL3602	Ki	5.29	5.29	5070.0	1
Cytochrome P450 2D26 CHEMBL2483	IC50	5.25	5.25	5600.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.98	4.9	10450.0	2
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	IC50	4.96	4.96	11050.0	1
Cytochrome P450 2D3 CHEMBL3057	IC50	4.73	4.73	18600.0	1
Taste receptor type 2 member 46 CHEMBL4523253	EC50	4.51	4.51	31000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	271.2	-	Chlorocebus sabaeus
CL	10.7	mL.min-1.g-1	Homo sapiens
CL	14.0	mL.min-1.g-1	Homo sapiens
CL	13.0	mL.min-1.g-1	Homo sapiens
CL	0.034	mL.min-1.g-1	Homo sapiens
CL	0.0542	mL.min-1.g-1	Homo sapiens
CL	0.0841	mL.min-1.g-1	Homo sapiens
CL	123.33	mL.min-1.kg-1	Homo sapiens
CL	25.4	mL.min-1.g-1	Homo sapiens
CL	24.2	mL.min-1.g-1	Homo sapiens
CL	12.8	mL.min-1.g-1	Homo sapiens
CL	123.33	mL.min-1.kg-1	Rattus norvegicus
CL	31030.0	mL.min-1.g-1	Homo sapiens
CL	31.0	mL.min-1.g-1	Homo sapiens
CL	59.7	mL.min-1.g-1	Homo sapiens
CL	-	-	Homo sapiens
CL	44.5	mL.min-1.g-1	Homo sapiens
CL	14.8	mL.min-1.kg-1	Homo sapiens
CL	83.3	mL.min-1.g-1	Mus musculus
CL	70.6	mL.min-1.kg-1	Mus musculus
CL	14.3	mL.min-1.kg-1	Homo sapiens
CL	135.3	mL.min-1.g-1	Mus musculus
CL	0.077	mL.min-1.kg-1	Mus musculus
CL	28.01	mL.min-1.g-1	Homo sapiens
Cmax	20.0	nM	Homo sapiens
Fu	0.82	-	Homo sapiens
Fu	0.72	-	Homo sapiens
Fu	0.93	-	Homo sapiens
T1/2	2.15	hr	Homo sapiens
T1/2	1.542	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium-dependent serotonin transporter	Ki	=	1.44	nM	8.84	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Sodium-dependent serotonin transporter	IC50	=	2.71	nM	8.57	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Sigma non-opioid intracellular receptor 1	Ki	=	10.0	nM	8.0	Displacement of [3H]-(+)-pentazocine from sigma-1 receptor in guinea pig brain m...	33372782
Sigma non-opioid intracellular receptor 1	IC50	=	15.2	nM	7.82	Displacement of [3H]pentazocine from sigma1 receptor in guinea pig membrane in p...	18029187
Cytochrome P450 2D6	IC50	=	40.8	nM	7.39	Inhibition of CYP2D6 in human liver microsomes incubated for 15 to 40 mins in pr...	35679690
Cytochrome P450 2D6	IC50	=	41.0	nM	7.39	Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substra...	36577220
Cytochrome P450 2D6	IC50	=	43.0	nM	7.37	Inhibition of CYP2D6 (unknown origin)	35797898
Cytochrome P450 2D6	IC50	=	52.0	nM	7.28	Inhibition of CYP2D6 (unknown origin)	36442370
Sigma non-opioid intracellular receptor 1	Ki	=	63.0	nM	7.2	Displacement of [3H]-(+)-pentazocine from sigma-1 receptor in guinea pig brain m...	33372782
Sigma non-opioid intracellular receptor 1	IC50	=	232.0	nM	6.63	Displacement of [3H]pentazocine from sigma1 receptor in guinea pig membrane	18029187
Cytochrome P450 2D6	IC50	=	242.0	nM	6.62	Inhibition of CYP2D6 (unknown origin)	38996652
Sigma non-opioid intracellular receptor 1	Ki	=	348.0	nM	6.46	Inhibition of [3H](+)-pentazocine binding to Sigma receptor type 1	15026077
Sodium channel alpha subunits; brain (Types I, II, III)	IC50	=	1300.0	nM	5.89	Inhibition of [3H]batrachotoxin binding to rat brain sodium channel	10498200
Glutamate NMDA receptor	IC50	=	1320.0	nM	5.88	Displacement of [3H]MK-801 from NMDA receptor in Wistar rat brain membranes by s...	26296478
Unchecked	Ki	=	1636.0	nM	5.79	DRUGMATRIX: Glutamate, NMDA, Phencyclidine radioligand binding (ligand: [3H] TCP...	-
Glutamate [NMDA] receptor	Ki	=	1680.0	nM	5.78	The compound was tested for its ability to block PCP N-methyl-D-aspartate glutam...	9464369
Cytochrome P450 2D6	IC50	=	1800.0	nM	5.75	Inhibition of MAMC O-dealkylation mediated by human Cytochrome P450 2D6 expresse...	12502361
Glutamate NMDA receptor	Ki	=	2246.0	nM	5.65	Binding affinity was measured against phencyclidine (PCP) receptor in rat using ...	8027978
Unchecked	IC50	=	2415.0	nM	5.62	DRUGMATRIX: Glutamate, NMDA, Phencyclidine radioligand binding (ligand: [3H] TCP...	-
Mas-related G-protein coupled receptor member X2	EC50	=	3235.94	nM	5.49	Agonist activity at MRGPRX2 (unknown origin) expressed in HTLA cells assessed as...	28288109

Literature References

PubMed	DOI	Target Context	# Activities
26296478	10.1016/j.bmcl.2015.08.017	Glutamate NMDA receptor	15
34506712	10.1021/acs.jmedchem.1c01007	ADMET	6
22942316	10.1124/dmd.112.047373	Liver microsome	6
29360358	10.1021/acs.jmedchem.7b01465	ADMET	6
22010218	10.1124/dmd.111.042200	Liver microsome	6
28288109	10.1038/nchembio.2334	Mas-related G-protein coupled receptor member X2	6
31597043	10.1021/acs.jmedchem.9b01301	Solute carrier family 22 member 1	4
28993106	10.1016/j.bmc.2017.09.037	ADMET	4
25464883	10.1016/j.bmc.2014.10.036	Rattus norvegicus	4
33515864	10.1016/j.ejmech.2021.113174	ADMET	4
31597043	10.1021/acs.jmedchem.9b01301	ADMET	3
32353859	10.1038/s41586-020-2286-9	SARS-CoV-2	3
33372782	10.1021/acs.jmedchem.0c01964	Sigma non-opioid intracellular receptor 1	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2A	3
22942316	10.1124/dmd.112.047373	Cytochrome P450 2D6	3
12166948	10.1021/jm020875j	Sodium channel alpha subunits; brain (Types I, II, III)	3
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	3
23378628	10.1124/dmd.112.050054	ADMET	3

Data from ChEMBL 36 via Core Engine