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Compound Detail

CHEMBL43064

CINNARIZINE
🧪 Phase II
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🧪 Phase II
C(=C/c1ccccc1)\CN1CCN(C(c2ccccc2)c2ccccc2)CC1

Basic Information

ChEMBL ID CHEMBL43064
Name CINNARIZINE
Phase Phase II
Structure Type MOL
InChI Key DERZBLKQOCDDDZ-JLHYYAGUSA-N
Therapeutic ✓ Yes

Known Names

516 MD 516-MD Aplactan Aplexal Artate Carecin Cerebolan Cerepar Cinaperazine Cinarizina Cinarizine Cinazyn +18 more
30
Targets
67
Activities
2
Assay Types
0
PK Parameters
20
Publications
30
Known Names
1
Indications
2
Mechanisms

Molecular Properties

368.5
MW (Da)
5.11
ALogP
2
HBA
0
HBD
6.5
PSA (Ų)
0.60
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 1962

Extended Properties

Molecular Formula C26H28N2
MW 368.52
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.74

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Voltage-gated L-type calcium channel blocker BLOCKER Voltage-gated L-type calcium channel
Histamine H1 receptor antagonist ANTAGONIST Histamine H1 receptor

Indications

Vertigo

ATC Classification

N07CA02
cinnarizine
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS
N07CA52
cinnarizine, combinations
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Activity Summary

IC50 41 meas. best 7.4
Ki 26 meas. best 8.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 8.06 8.06 8.6 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.77 7.77 17.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 7.4 7.4 40.0 1
Histamine H1 receptor
CHEMBL231
IC50 7.13 7.13 74.0 1
D(3) dopamine receptor
CHEMBL234
Ki 7.07 7.07 86.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.02 7.02 95.0 1
Unchecked
CHEMBL612545
Ki 7.0 6.406 99.0 5
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.99 6.99 103.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.79 6.79 162.0 1
Unchecked
CHEMBL612545
IC50 6.79 6.306 161.0 5
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.78 6.78 167.0 1
D(3) dopamine receptor
CHEMBL234
IC50 6.6 6.6 252.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.59 6.59 259.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.44 6.44 360.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 6.36 6.36 440.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.35 6.35 444.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.33 6.33 465.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 6.3 6.3 502.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.29 6.29 510.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.26 6.26 545.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.24 6.24 573.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.24 6.24 579.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.22 6.22 605.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 6.21 6.21 619.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 6.19 6.19 652.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.14 6.14 731.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 6.12 6.12 759.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 6.12 6.12 762.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.11 6.11 777.0 1
D(2) dopamine receptor
CHEMBL217
IC50 6.11 6.11 776.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 6.04 6.04 906.0 1
Mu-type opioid receptor
CHEMBL233
Ki 6.04 6.04 922.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.99 5.99 1023.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 5.96 5.96 1083.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.96 5.96 1090.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 5.93 5.93 1167.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.88 5.88 1304.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.79 5.79 1641.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 5.72 5.72 1919.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.65 5.65 2242.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.64 5.64 2272.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.6 5.6 2513.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.55 5.55 2832.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.55 5.55 2808.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 5.44 5.44 3660.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.3 5.0833 5011.9 6
A549
CHEMBL392
IC50 5.01 5.01 9800.0 1
LoVo
CHEMBL614721
IC50 4.98 4.98 10500.0 1
MIA PaCa-2
CHEMBL614725
IC50 4.96 4.96 11100.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.87 4.87 13500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 8.622 nM 8.06 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Sigma non-opioid intracellular receptor 1 IC50 = 40.0 nM 7.4 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Histamine H1 receptor IC50 = 74.0 nM 7.13 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
D(3) dopamine receptor Ki = 86.0 nM 7.07 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-2C adrenergic receptor Ki = 95.0 nM 7.02 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Unchecked Ki = 99.0 nM 7.0 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
5-hydroxytryptamine receptor 2A Ki = 103.0 nM 6.99 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Unchecked IC50 = 161.0 nM 6.79 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Muscarinic acetylcholine receptor M3 Ki = 162.0 nM 6.79 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-2A adrenergic receptor Ki = 167.0 nM 6.78 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
D(3) dopamine receptor IC50 = 252.0 nM 6.6 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor Ki = 259.0 nM 6.59 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
5-hydroxytryptamine receptor 2A IC50 = 360.0 nM 6.44 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Unchecked Ki = 377.0 nM 6.42 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Unchecked IC50 = 414.0 nM 6.38 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 440.0 nM 6.36 Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol... 2579237
Alpha-2A adrenergic receptor IC50 = 444.0 nM 6.35 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
5-hydroxytryptamine receptor 2B Ki = 465.0 nM 6.33 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Alpha-1B adrenergic receptor Ki = 502.0 nM 6.3 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 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 Alpha-2A adrenergic receptor 3
16680159 10.1038/nchembio790 PC-3 2
20426472 10.1021/jm100254w Cruzipain 2
37468498 10.1038/s41467-023-40064-9 Adenosine receptor A3 2

Data from ChEMBL 36 via Core Engine