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Compound Detail

CHEMBL833

TICLOPIDINE
💊 Approved Drug
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💊 Approved Drug
Clc1ccccc1CN1CCc2sccc2C1

Basic Information

ChEMBL ID CHEMBL833
Name TICLOPIDINE
Phase Approved
Structure Type MOL
InChI Key PHWBOXQYWZNQIN-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1201394

Known Names

Ticlopidin-puren Ticlopidina Ticlopidine
16
Targets
36
Activities
2
Assay Types
6
PK Parameters
20
Publications
3
Known Names
3
Indications

Molecular Properties

263.8
MW (Da)
3.96
ALogP
2
HBA
0
HBD
3.2
PSA (Ų)
0.79
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Year 1978

Extended Properties

Molecular Formula C14H14ClNS
MW 263.79
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -2.47

Indications

Thrombosis Carotid Stenosis Peripheral Arterial Disease

ATC Classification

B01AC05
ticlopidine
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

IC50 26 meas. best 6.68
Ki 10 meas. best 6.86

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.86 6.86 139.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.84 6.84 143.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.77 6.77 171.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.75 6.75 179.0 1
Cytochrome P450 2B6
CHEMBL4729
Ki 6.7 6.4 200.0 2
Cytochrome P450 2B6
CHEMBL4729
IC50 6.68 5.6867 210.0 3
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.52 6.52 304.0 1
Platelet
CHEMBL4296519
IC50 6.44 6.44 360.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.42 6.42 382.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.37 6.37 426.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 6.17 5.5367 667.8 3
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.93 5.93 1175.0 1
Unchecked
CHEMBL612545
Ki 5.83 5.765 1493.0 2
Unchecked
CHEMBL612545
IC50 5.65 5.57 2239.0 2
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.5 5.465 3180.0 2
Cytochrome P450 2C19
CHEMBL3622
Ki 5.48 4.77 3300.0 2
Cytochrome P450 2D6
CHEMBL289
IC50 5.32 5.26 4800.0 2
Cytochrome P450 1A2
CHEMBL3356
IC50 5.07 5.07 8590.0 1
Cytochrome P450 2J2
CHEMBL3491
IC50 4.66 4.66 21800.0 1
Bile salt export pump
CHEMBL6020
IC50 4.57 4.35 26950.0 2
Cytochrome P450 2C9
CHEMBL3397
IC50 4.51 4.51 31100.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 4.49 4.49 32700.0 1
Bile salt export pump
CHEMBL2073674
IC50 4.31 4.31 49000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 35.0 mL.min-1.g-1 Homo sapiens
CL 56.23 uL.min-1.(10^6cells)-1 Homo sapiens
CL 150.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 0.000431 mL.min-1.g-1 Homo sapiens
CL 0.00203 mL.min-1.g-1 Homo sapiens
CL 2.461 uL/min Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-2B adrenergic receptor Ki = 139.0 nM 6.86 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-2A adrenergic receptor Ki = 143.0 nM 6.84 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Alpha-2C adrenergic receptor Ki = 171.0 nM 6.77 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Sigma non-opioid intracellular receptor 1 Ki = 179.0 nM 6.75 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Cytochrome P450 2B6 Ki = 200.0 nM 6.7 Mechanism based inhibition of human cytochrome P450 2B6 measured by bupropion hy... 16248836
Cytochrome P450 2B6 IC50 = 210.0 nM 6.68 Inhibition of CYP2B6 in human liver microsomes using bupropion as substrate incu... 35609303
Alpha-2B adrenergic receptor IC50 = 304.0 nM 6.52 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Platelet IC50 = 360.0 nM 6.44 Inhibition of ADP-induced platelet aggregation in New Zealand White rabbit 38704941
Alpha-2A adrenergic receptor IC50 = 382.0 nM 6.42 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Sigma non-opioid intracellular receptor 1 IC50 = 426.0 nM 6.37 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Cytochrome P450 2B6 IC50 = 600.0 nM 6.22 Inhibition of recombinant human CYP2B6 by P450-Glo luminescence assay 27145071
Cytochrome P450 2C19 IC50 = 667.8 nM 6.17 DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Cytochrome P450 2B6 Ki = 800.0 nM 6.1 Mechanism based inhibition of human cytochrome P450 2B6 measured by bupropion hy... 16248836
Alpha-2C adrenergic receptor IC50 = 1175.0 nM 5.93 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Cytochrome P450 2C19 IC50 = 1300.0 nM 5.89 Inhibition of CYP2C19 in human liver microsomes using (S)-mephenytoin as substra... 26962886
Unchecked Ki = 1493.0 nM 5.83 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
Unchecked Ki = 2007.0 nM 5.7 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Unchecked IC50 = 2239.0 nM 5.65 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
NON-PROTEIN TARGET IC50 = 3180.0 nM 5.5 Antiplatelet activity in rabbit platelet rich plasma assessed as inhibition of A... 22137848
Unchecked IC50 = 3262.0 nM 5.49 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1398
- 10.6019/CHEMBL3885881 Rattus norvegicus 227
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
21156812 10.1124/dmd.110.037101 Cytochrome P450 2B6 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
21156812 10.1124/dmd.110.037101 Cytochrome P450 2B4 6
21156812 10.1124/dmd.110.037101 Liver microsome 5
37468498 10.1038/s41467-023-40064-9 Bile acid receptor 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
16248836 10.2174/138920005774330639 Cytochrome P450 2B6 4
21467212 10.1124/dmd.111.039180 Liver microsome 3
10346922 10.1021/jm981103j Rattus norvegicus 3
- 10.6019/CHEMBL3301361 ADMET 3
16248836 10.2174/138920005774330639 Cytochrome P450 2C19 3
- 10.1039/C4MD00196F ADMET 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3

Data from ChEMBL 36 via Core Engine