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Compound Detail

CHEMBL648

CYCLIZINE
💊 Approved Drug
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💊 Approved Drug
CN1CCN(C(c2ccccc2)c2ccccc2)CC1

Basic Information

ChEMBL ID CHEMBL648
Name CYCLIZINE
Phase Approved
Structure Type MOL
InChI Key UVKZSORBKUEBAZ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ciclizina Cyclizine NSC-26608
17
Targets
38
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names
1
Indications

Molecular Properties

266.4
MW (Da)
3.02
ALogP
2
HBA
0
HBD
6.5
PSA (Ų)
0.84
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Achiral

Routes of Administration

Parenteral

Flags

Natural Product

Extended Properties

Molecular Formula C18H22N2
MW 266.39
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.90

Indications

Hypersensitivity

ATC Classification

R06AE03
cyclizine
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE
R06AE53
cyclizine, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

IC50 19 meas. best 7.42
Ki 18 meas. best 8.35
EC50 1 meas. best 5.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 8.35 8.35 4.4 1
Histamine H1 receptor
CHEMBL231
IC50 7.42 7.42 38.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 7.19 7.19 64.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.92 6.92 119.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.8 6.8 159.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.79 6.79 163.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.65 6.65 225.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.62 6.62 238.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.43 6.43 373.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.38 6.38 412.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.34 6.34 455.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.27 6.27 535.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.24 6.24 582.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.22 6.22 606.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.22 6.22 597.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 6.2 6.2 633.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 6.17 6.17 675.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 6.13 6.13 748.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 6.12 6.12 763.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 6.07 6.07 852.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 5.99 5.99 1021.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.99 5.99 1016.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 5.94 5.94 1158.0 1
Hepatitis C virus
CHEMBL379
EC50 5.94 5.94 1140.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 5.92 5.92 1215.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 5.86 5.86 1379.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.81 5.81 1551.0 1
Unchecked
CHEMBL612545
Ki 5.68 5.555 2088.0 4
Alpha-1B adrenergic receptor
CHEMBL315
IC50 5.6 5.6 2492.0 1
Unchecked
CHEMBL612545
IC50 5.6 5.485 2518.0 4
D(3) dopamine receptor
CHEMBL234
IC50 5.52 5.52 2992.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 5.21 5.21 6217.5 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 4.443 nM 8.35 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Histamine H1 receptor IC50 = 38.0 nM 7.42 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
5-hydroxytryptamine receptor 2A Ki = 64.0 nM 7.19 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M4 Ki = 119.0 nM 6.92 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 159.0 nM 6.8 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 Ki = 163.0 nM 6.79 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2A IC50 = 225.0 nM 6.65 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B Ki = 238.0 nM 6.62 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B IC50 = 373.0 nM 6.43 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M2 Ki = 412.0 nM 6.38 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 Ki = 455.0 nM 6.34 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2C Ki = 535.0 nM 6.27 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Alpha-2A adrenergic receptor Ki = 582.0 nM 6.24 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Sodium-dependent dopamine transporter Ki = 606.0 nM 6.22 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Alpha-1D adrenergic receptor Ki = 597.0 nM 6.22 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Muscarinic acetylcholine receptor M5 IC50 = 633.0 nM 6.2 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 IC50 = 675.0 nM 6.17 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 IC50 = 748.0 nM 6.13 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Sodium-dependent dopamine transporter IC50 = 763.0 nM 6.12 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Muscarinic acetylcholine receptor M4 IC50 = 852.0 nM 6.07 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 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
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1-6 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
22122484 10.1021/jm201082a ADMET 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1A9 1
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1A3 1
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1A1 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
17428028 10.1021/ci6004542 Phospholipidosis 1

Data from ChEMBL 36 via Core Engine