CINNARIZINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC N07CA02
UNII 3DI2E1X18L
EPA CompTox DTXSID3022821

Structure

InChI Key DERZBLKQOCDDDZ-JLHYYAGUSA-N
Smiles C(=C/c1ccccc1)\CN1CCN(C(c2ccccc2)c2ccccc2)CC1
InChI
InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H28N2
Molecular Weight 368.52
AlogP 5.11
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 6.0
Polar Surface Area 6.48
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 28.0

Bioactivity

Mechanism of Action Action Reference
Histamine H1 receptor antagonist ANTAGONIST PubMed PubMed PubMed PubMed PubMed PubMed PubMed
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1F
Organism : Homo sapiens
O60840 ENSG00000102001
Protein: Histamine H1 receptor
Description: Histamine H1 receptor
Organism : Homo sapiens
P35367 ENSG00000196639
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1D
Organism : Homo sapiens
Q01668 ENSG00000157388
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1S
Organism : Homo sapiens
Q13698 ENSG00000081248
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1C
Organism : Homo sapiens
Q13936 ENSG00000151067
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 440 - - 95
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 103
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 15700-15700 - - -
Assay Description Organism Bioactivity Reference
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex Cavia porcellus 440.0 nM
Inhibition of Batrachotoxin [3H]BTX-B binding to high affinity sites on voltage dependent sodium channels of guinea pig cerebral cortex vesicular preparation at 10 uM Cavia porcellus 94.6 %
DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 605.0 nM
DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 762.0 nM DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 162.0 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 510.0 nM
DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 759.0 nM DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 545.0 nM
DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine) None 922.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 619.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 360.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 103.0 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 777.0 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 906.0 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 502.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 573.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 444.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 167.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 652.0 nM DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 95.0 nM
DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 823.0 nM DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 732.0 nM
DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand: [3H] Nitrendipine) Rattus norvegicus 846.0 nM DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand: [3H] Nitrendipine) Rattus norvegicus 544.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 731.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 465.0 nM
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 579.0 nM
DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 40.0 nM DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 17.0 nM
DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) Rattus norvegicus 161.0 nM DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) Rattus norvegicus 99.0 nM
DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 414.0 nM DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 377.0 nM
DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 624.0 nM DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 607.0 nM
DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 776.0 nM DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 259.0 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 252.0 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 86.0 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 74.0 nM DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 8.622 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 185.06 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 102.69 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 5.27 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 31.02 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.698 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.1 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.06 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.06 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.1 %

Related Entries

Cross References

Resources Reference
ChEBI 31403
ChEMBL CHEMBL43064
DrugCentral 654
FDA SRS 3DI2E1X18L
Guide to Pharmacology 9072
PubChem 1547484
SureChEMBL SCHEMBL44957
ZINC ZINC000019632891
CONTENTS