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Compound Detail

CHEMBL395110

MEPAZINE
💊 Approved Drug
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💊 Approved Drug
CN1CCCC(CN2c3ccccc3Sc3ccccc32)C1

Basic Information

ChEMBL ID CHEMBL395110
Name MEPAZINE
Phase Approved
Structure Type MOL
InChI Key CBHCDHNUZWWAPP-UHFFFAOYSA-N

Known Names

III-2318 Lacumin Mepasin Mepazin Mepazine base Meprazine Mesapin Nothiazine P-391 Pacatal Pacatal base Pacatol +5 more
20
Targets
47
Activities
2
Assay Types
0
PK Parameters
20
Publications
17
Known Names

Molecular Properties

310.5
MW (Da)
4.63
ALogP
3
HBA
0
HBD
6.5
PSA (Ų)
0.80
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Racemic

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C19H22N2S
MW 310.47
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.91

Activity Summary

IC50 26 meas. best 7.57
Ki 21 meas. best 8.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 8.51 8.51 3.1 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 7.72 7.72 19.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 7.72 7.72 19.0 1
Histamine H1 receptor
CHEMBL231
IC50 7.57 7.57 27.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 7.55 7.55 28.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.47 7.47 34.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 7.4 7.4 40.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 7.4 7.4 40.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 7.24 7.24 58.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 7.21 7.21 61.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.17 7.17 67.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.12 7.12 76.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 7.1 7.1 79.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.96 6.96 110.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 6.86 6.86 137.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 6.86 6.86 137.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 6.84 6.84 144.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.75 6.75 180.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.74 6.74 181.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 6.72 6.72 191.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.7 6.7 201.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.59 6.59 259.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.49 6.49 327.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.42 6.42 385.0 1
Unchecked
CHEMBL612545
Ki 6.41 5.9567 388.0 3
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.4 6.4 397.0 1
Mucosa-associated lymphoid tissue lymphoma translocation protein 1
CHEMBL3632452
IC50 6.38 6.155 420.0 4
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.3 6.3 495.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.29 6.29 514.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.26 6.26 546.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 6.25 6.25 565.0 1
Unchecked
CHEMBL612545
IC50 6.2 5.92 631.0 4
D(3) dopamine receptor
CHEMBL234
Ki 6.17 6.17 681.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.07 6.07 853.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.84 5.84 1456.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 5.74 5.74 1837.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.73 5.73 1861.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.73 5.73 1877.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.7 5.7 2006.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 3.126 nM 8.51 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Muscarinic acetylcholine receptor M1 Ki = 19.0 nM 7.72 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M4 Ki = 19.0 nM 7.72 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Histamine H1 receptor IC50 = 27.0 nM 7.57 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Muscarinic acetylcholine receptor M5 Ki = 28.0 nM 7.55 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-1B adrenergic receptor Ki = 34.0 nM 7.47 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Muscarinic acetylcholine receptor M5 IC50 = 40.0 nM 7.4 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 40.0 nM 7.4 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-1A adrenergic receptor Ki = 58.0 nM 7.24 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1B adrenergic receptor IC50 = 61.0 nM 7.21 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1D adrenergic receptor Ki = 67.0 nM 7.17 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Sigma non-opioid intracellular receptor 1 Ki = 76.0 nM 7.12 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Muscarinic acetylcholine receptor M1 IC50 = 79.0 nM 7.1 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2A Ki = 110.0 nM 6.96 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M4 IC50 = 137.0 nM 6.86 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-1D adrenergic receptor IC50 = 137.0 nM 6.86 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1A adrenergic receptor IC50 = 144.0 nM 6.84 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Sigma non-opioid intracellular receptor 1 IC50 = 180.0 nM 6.75 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Alpha-2B adrenergic receptor Ki = 181.0 nM 6.74 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Muscarinic acetylcholine receptor M3 IC50 = 191.0 nM 6.72 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -

Literature References

PubMed DOI Target Context # Activities
27085674 10.1016/j.bmc.2016.03.035 Mucosa-associated lymphoid tissue lymphoma translocation protein 1 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
21624500 10.1016/j.drudis.2011.05.007 Hepatotoxicity 1
- 10.1039/C4MD00030G Serine/threonine-protein kinase pim-1 1
38349664 10.1021/acs.jmedchem.3c02031 Mucosa-associated lymphoid tissue lymphoma translocation protein 1 1
17407813 10.1016/j.bmcl.2007.03.064 5-hydroxytryptamine receptor 2C 1
17407813 10.1016/j.bmcl.2007.03.064 5-hydroxytryptamine receptor 2A 1
17407813 10.1016/j.bmcl.2007.03.064 5-hydroxytryptamine receptor 1A 1
34181850 10.1021/acs.jmedchem.1c00466 Mucosa-associated lymphoid tissue lymphoma translocation protein 1 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
17407813 10.1016/j.bmcl.2007.03.064 D(3) dopamine receptor 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 Bile salt export pump 1
17407813 10.1016/j.bmcl.2007.03.064 D(2) dopamine receptor 1

Data from ChEMBL 36 via Core Engine