TICLOPIDINE

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Synonyms
Status
Molecule Category Free-form
ATC B01AC05
UNII OM90ZUW7M1
EPA CompTox DTXSID5023669

Structure

InChI Key PHWBOXQYWZNQIN-UHFFFAOYSA-N
Smiles Clc1ccccc1CN1CCc2sccc2C1
InChI
InChI=1S/C14H14ClNS/c15-13-4-2-1-3-11(13)9-16-7-5-14-12(10-16)6-8-17-14/h1-4,6,8H,5,7,9-10H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H14ClNS
Molecular Weight 263.79
AlogP 3.96
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 2.0
Polar Surface Area 3.24
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 17.0

Metabolites Network

visNetwork
Assay Description Organism Bioactivity Reference
Compound was evaluated for inhibition of ADP-mediated platelet aggregation Homo sapiens 48.5 %
In vivo inhibitory activity after 120 min of 100 mg/kg oral administration induced by I-BOP in rats Rattus norvegicus 57.1 %
In vivo inhibitory activity after 120 min of 100 mg/kg oral administration induced by arachidonic acid in rats Rattus norvegicus 0.9 %
In vivo inhibitory activity after 120 min of 100 mg/kg oral administration induced by collagen in rats Rattus norvegicus 98.7 %
Mechanism based inhibition of human cytochrome P450 2B6 measured by bupropion hydroxylation using human liver microsomes Homo sapiens 200.0 nM
Mechanism based inhibition of human cytochrome P450 2B6 measured by bupropion hydroxylation using recombinant CYP2B6 Homo sapiens 800.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 382.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 143.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 304.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 139.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 171.0 nM
DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 426.0 nM DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 179.0 nM
DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 667.8 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 19.4 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 0.2 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 23.0 %
Antiplatelet activity in rabbit platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation at 0.1 mM incubated for 5 mins prior to ADP challenge measured after 5 mins by Born's turbidimetric method relative to control Oryctolagus cuniculus 26.45 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 36.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system Homo sapiens 26.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 10 uM by LC/MS system Homo sapiens 60.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 10 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 0.1 uM by LC/MS system Homo sapiens 35.0 %
Inhibition of human CYP2C19 at 10 uM preincubated for 10 mins with cofactor followed by mixture of enzyme-substrate addition by fluorescence assay relative to control Homo sapiens 104.4 %
Antiplatelet activity in rabbit platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation at 0.1 mM preincubated for 5 mins followed by ADP addition measured after 5 mins by Born's turbidimetric method relative to control Oryctolagus cuniculus 11.53 %
Inhibition of CYP2B6 in human liver microsomes at 10 uM incubated for 5 mins followed by NADPH addition by LC-MS/MS analysis relative to control Homo sapiens 98.0 %
Inhibition of CYP2C19 in human liver microsomes using smephenytoin as substrate at 10 uM preincubated for 5 mins followed by NADPH addition measured after 20 mins by LC-MS/MS analysis relative to control Homo sapiens 89.0 %
Inhibition of recombinant human CYP2B6 by P450-Glo luminescence assay Homo sapiens 600.0 nM
Inhibition of human CYP2C19 in human liver microsomes at at 50 times IC50 concentration relative to control Homo sapiens 98.7 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 20.54 %
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 0.13 % 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 0.13 %
Inhibition of CYP2C19 in human liver microsomes at 10 uM using mephenytoin as substrate preincubated for 5 mins followed by NADPH addition and measured after 20 mins by LC-MS/MS analysis relative to control Homo sapiens 88.0 %
Inhibition of CYP2C19 in human liver Microsome using S-mephenytoin as substrate preincubated for 10 mins followed by NADPH addition and further incubated for 10 mins as substrate by LC-MS/MS analysis relative to control Homo sapiens 81.5 %
Inhibition of CYP2C19 (unknown origin) at 3 uM using S-mephenytoin as substrate relative to control Homo sapiens 67.0 %

Cross References

Resources Reference
ChEBI 9588
ChEMBL CHEMBL833
DrugBank DB00208
DrugCentral 2657
FDA SRS OM90ZUW7M1
Human Metabolome Database HMDB0014353
Guide to Pharmacology 7307
KEGG C07140
PDB TIC
PharmGKB PA451686
PubChem 5472
SureChEMBL SCHEMBL4204
ZINC ZINC000019594599
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