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Compound Detail

CHEMBL1626

CLEMASTINE
💊 Approved Drug
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💊 Approved Drug
CN1CCC[C@@H]1CCO[C@](C)(c1ccccc1)c1ccc(Cl)cc1

Basic Information

ChEMBL ID CHEMBL1626
Name CLEMASTINE
Phase Approved
Structure Type MOL
InChI Key YNNUSGIPVFPVBX-NHCUHLMSSA-N
Therapeutic ✓ Yes

Known Names

Clemastin Clemastina Clemastine HS-592 NSC-756685
31
Targets
72
Activities
2
Assay Types
2
PK Parameters
20
Publications
5
Known Names
10
Indications

Molecular Properties

343.9
MW (Da)
5.10
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.72
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -astine
USAN Year 1969

Extended Properties

Molecular Formula C21H26ClNO
MW 343.90
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.40

Indications

Hypersensitivity Pruritus Angioedema Dermatitis Williams Syndrome Multiple Sclerosis Multiple Sclerosis, Relapsing-Remitting Optic Neuritis Schizophrenia Urticaria

ATC Classification

D04AA14
clemastine
Level 1: DERMATOLOGICALS
Level 2: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
R06AA04
clemastine
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE
R06AA54
clemastine, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

Ki 38 meas. best 10.31
IC50 34 meas. best 9.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 10.31 10.31 0.0 1
Histamine H1 receptor
CHEMBL231
IC50 9.38 9.38 0.4 1
D(3) dopamine receptor
CHEMBL234
Ki 8.6 8.6 2.5 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 8.56 7.915 2.8 2
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 8.22 7.89 6.0 2
D(3) dopamine receptor
CHEMBL234
IC50 8.13 8.13 7.3 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 8.08 8.08 8.4 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 8.08 7.665 8.3 2
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.04 8.04 9.2 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 8.0 7.925 10.0 2
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.85 7.25 14.0 2
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.82 7.82 15.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 7.7 7.7 20.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 7.7 7.7 19.9 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 7.68 7.68 21.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.64 7.64 23.0 1
Sigma intracellular receptor 2
CHEMBL4105907
Ki 7.6 7.6 25.1 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 7.5 7.5 32.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.5 7.5 32.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 7.47 7.47 34.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 7.44 7.44 36.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.44 7.44 36.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 7.41 7.41 39.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.39 7.39 41.0 1
D(2) dopamine receptor
CHEMBL217
Ki 7.35 7.35 45.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.28 7.28 52.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 7.28 7.28 53.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 7.16 6.965 69.0 2
Alpha-1B adrenergic receptor
CHEMBL315
IC50 7.13 7.13 74.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 7.11 7.11 77.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 7.02 7.02 95.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.0 7.0 99.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.93 6.93 117.5 1
D(2) dopamine receptor
CHEMBL217
IC50 6.87 6.87 136.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.85 6.585 142.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 6.8 6.645 158.5 2
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.74 6.74 183.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 6.66 6.66 220.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.51 6.51 311.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 6.45 6.45 359.0 1
Histamine H2 receptor
CHEMBL1941
Ki 6.44 6.44 364.0 1
Histamine H2 receptor
CHEMBL1941
IC50 6.43 6.43 370.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.4 6.4 395.1 1
Unchecked
CHEMBL612545
Ki 6.35 6.1175 448.0 4
Unchecked
CHEMBL612545
IC50 6.29 5.7171 508.0 7
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.27 6.27 538.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 6.22 6.22 600.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 6.17 6.17 678.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.12 6.12 767.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 5.81 5.81 1535.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 190.4 - Chlorocebus sabaeus
F 49.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 0.049 nM 10.31 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Histamine H1 receptor IC50 = 0.421 nM 9.38 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
D(3) dopamine receptor Ki = 2.491 nM 8.6 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Muscarinic acetylcholine receptor M4 Ki = 2.773 nM 8.56 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 Ki = 6.016 nM 8.22 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
D(3) dopamine receptor IC50 = 7.335 nM 8.13 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Muscarinic acetylcholine receptor M5 IC50 = 8.373 nM 8.08 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 8.253 nM 8.08 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2A Ki = 9.196 nM 8.04 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Sigma non-opioid intracellular receptor 1 Ki = 10.0 nM 8.0 Displacement of [3H]-pentazocin from the Sigma1 receptor 32353859
Sigma non-opioid intracellular receptor 1 Ki = 14.0 nM 7.85 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Alpha-2C adrenergic receptor Ki = 14.0 nM 7.85 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Alpha-1D adrenergic receptor Ki = 15.0 nM 7.82 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Muscarinic acetylcholine receptor M1 Ki = 19.95 nM 7.7 Activity of compound against Muscarinic acetylcholine receptor M1 (CHRM1) by dis... 32353859
Muscarinic acetylcholine receptor M4 IC50 = 20.0 nM 7.7 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-1A adrenergic receptor Ki = 21.0 nM 7.68 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2B Ki = 23.0 nM 7.64 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Sigma intracellular receptor 2 Ki = 25.12 nM 7.6 Displacement of [3H]-DTG from the Sigma2 receptor 32353859
Muscarinic acetylcholine receptor M5 Ki = 27.54 nM 7.56 Activity of compound against Muscarinic acetylcholine receptor M5 (CHRM5) by dis... 32353859
Alpha-1D adrenergic receptor IC50 = 32.0 nM 7.5 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 492
- 10.5281/zenodo.13943903 ADMET 86
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
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 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
32353859 10.1038/s41586-020-2286-9 SARS-CoV-2 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 3
- 10.6019/CHEMBL3301361 No relevant target 2
22931300 10.1021/tx300075j Liver microsomes 2
37468498 10.1038/s41467-023-40064-9 Adenosine receptor A1 2

Data from ChEMBL 36 via Core Engine