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Compound Detail

CHEMBL1909072

PIPAMAZINE
💊 Approved Drug
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💊 Approved Drug
NC(=O)C1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc32)CC1

Basic Information

ChEMBL ID CHEMBL1909072
Name PIPAMAZINE
Phase Approved
Structure Type MOL
InChI Key OSJJYEUEJRVVOD-UHFFFAOYSA-N

Known Names

Pipamazina Pipamazine
22
Targets
49
Activities
2
Assay Types
0
PK Parameters
4
Publications
2
Known Names
1
Mechanisms

Molecular Properties

402.0
MW (Da)
4.53
ALogP
4
HBA
1
HBD
49.6
PSA (Ų)
0.80
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn

Extended Properties

Molecular Formula C21H24ClN3OS
MW 401.96
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -1.62

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Drug Warnings

Withdrawn
hepatotoxicity
associated with hepatic lesions
Country: United States   Year: 1969
Withdrawn
hepatotoxicity
associated with hepatic lesions
Country: United States   Year: 1969
Withdrawn
hepatotoxicity
associated with hepatic lesions
Country: United States   Year: 1969

Activity Summary

IC50 25 meas. best 8.76
Ki 24 meas. best 9.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 9.26 9.26 0.6 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 9.11 9.11 0.8 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 9.02 9.02 1.0 1
Histamine H1 receptor
CHEMBL231
Ki 8.94 8.94 1.2 1
D(2) dopamine receptor
CHEMBL217
Ki 8.87 8.87 1.4 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 8.85 8.85 1.4 1
D(3) dopamine receptor
CHEMBL234
Ki 8.8 8.8 1.6 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 8.76 8.76 1.7 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 8.71 8.71 1.9 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 8.71 8.71 1.9 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 8.68 8.68 2.1 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 8.59 8.59 2.6 1
D(2) dopamine receptor
CHEMBL217
IC50 8.39 8.39 4.0 1
D(3) dopamine receptor
CHEMBL234
IC50 8.33 8.33 4.7 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 8.29 8.29 5.1 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 8.19 8.19 6.5 1
Histamine H1 receptor
CHEMBL231
IC50 8.0 8.0 9.9 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.96 7.96 11.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 7.8 7.8 16.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.66 7.66 22.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 7.6 7.6 25.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.51 7.51 31.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 7.5 7.5 32.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 7.35 7.35 45.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.32 7.32 48.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 7.31 7.31 49.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.28 7.28 52.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 7.18 7.18 66.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 7.0 7.0 100.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 6.95 6.95 112.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.94 6.94 114.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.46 6.46 346.0 1
Unchecked
CHEMBL612545
Ki 6.43 6.0125 372.0 4
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 6.35 6.35 450.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.35 6.35 446.0 1
Unchecked
CHEMBL612545
IC50 6.22 5.905 604.0 4
Sodium-dependent serotonin transporter
CHEMBL228
IC50 6.19 6.19 651.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 5.99 5.99 1018.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 5.86 5.86 1367.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 5.75 5.75 1782.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 5.65 5.65 2259.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 5.52 5.52 3007.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 5.5 5.5 3144.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.554 nM 9.26 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-2B adrenergic receptor Ki = 0.786 nM 9.11 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-1D adrenergic receptor Ki = 0.955 nM 9.02 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Histamine H1 receptor Ki = 1.154 nM 8.94 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
D(2) dopamine receptor Ki = 1.35 nM 8.87 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
Alpha-1B adrenergic receptor Ki = 1.417 nM 8.85 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
D(3) dopamine receptor Ki = 1.586 nM 8.8 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-2B adrenergic receptor IC50 = 1.722 nM 8.76 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-1D adrenergic receptor IC50 = 1.944 nM 8.71 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2A IC50 = 1.938 nM 8.71 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-1A adrenergic receptor Ki = 2.081 nM 8.68 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1B adrenergic receptor IC50 = 2.56 nM 8.59 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
D(2) dopamine receptor IC50 = 4.05 nM 8.39 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
D(3) dopamine receptor IC50 = 4.671 nM 8.33 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-1A adrenergic receptor IC50 = 5.142 nM 8.29 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2C adrenergic receptor Ki = 6.468 nM 8.19 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Histamine H1 receptor IC50 = 9.939 nM 8.0 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
5-hydroxytryptamine receptor 2C Ki = 11.0 nM 7.96 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
D(1A) dopamine receptor Ki = 16.0 nM 7.8 DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) -
5-hydroxytryptamine receptor 2C IC50 = 22.0 nM 7.66 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -

Literature References

PubMed DOI Target Context # Activities
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
21624500 10.1016/j.drudis.2011.05.007 Hepatotoxicity 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine