Identification

Name
Ticlopidine
Accession Number
DB00208  (APRD01257)
Type
Small Molecule
Groups
Approved
Description

Ticlopidine is an effective inhibitor of platelet aggregation. It is a prodrug that is metabolised to an active form, which blocks the ADP receptor that is involved in GPIIb/IIIa receptor activation leading to platelet aggregation. Ticlopidine is marketed under the brand name Ticlid and is indicated for patients who cannot take aspirin or in whom aspirin has not worked to prevent a thrombotic stroke. The FDA label includes a black-box warning of neutropenia, aplastic anemia, thrombotic thrombocytopenia purpura, and agranulocytosis, so it is necessary to monitor patients' WBC and platelets when they are taking ticlopidine.

Structure
Thumb
Synonyms
  • Ticlopidina
  • Ticlopidinum
Product Ingredients
IngredientUNIICASInChI Key
Ticlopidine HydrochlorideA1L4914FMF53885-35-1MTKNGOHFNXIVOS-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sandoz TiclopidineTablet250 mgOralSandoz Canada Incorporated2001-05-142011-10-21Canada
TiclidTablet, film coated250 mg/1OralGenentech, Inc.1991-10-312011-07-18Us
TiclidTablet, film coated250 mg/1OralPhysicians Total Care, Inc.1996-06-052001-06-30Us
Ticlid 250mg TabletsTablet250 mgOralHoffmann La Roche1995-12-312006-07-25Canada
Ticlid Tab 250mgTablet250 mgOralSyntex Inc.1992-12-311996-09-30Canada
TiclopidineTablet250 mgOralAa Pharma Inc1998-03-30Not applicableCanada
TiclopidineTablet250 mgOralSanis Health Inc2010-02-162014-08-01Canada
Ticlopidine-250Tablet250 mgOralPro Doc Limitee1999-11-182010-07-13Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-ticlopidine - Tab 250mgTablet250 mgOralAltimed Pharma Inc.1996-12-312005-05-27Canada
Dom-ticlopidineTablet250 mgOralDominion Pharmacal2001-05-232016-10-25Canada
Mylan-ticlopidineTablet250 mgOralMylan Pharmaceuticals1999-03-042017-01-09Canada
Nu-ticlopidine 250 mgTablet250 mgOralNu Pharm Inc1998-06-092012-09-04Canada
PMS-ticlopidineTablet250 mgOralPharmascience Inc2001-02-232016-10-28Canada
Teva-ticlopidineTablet250 mgOralTeva2002-07-30Not applicableCanada
Ticlopidine HydrochlorideTablet, film coated250 mg/1OralCarilion Materials Management1999-09-07Not applicableUs68151 007920180907 15195 1f7kwyl
Ticlopidine HydrochlorideTablet, film coated250 mg/1OralAv Kare, Inc.2014-03-202015-06-09Us
Ticlopidine HydrochlorideTablet, film coated250 mg/1OralTeva1999-09-072015-09-30Us00093 0154 01 nlmimage10 6f29b7bd
Ticlopidine HydrochlorideTablet, film coated250 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2002-09-26Not applicableUs57664 0327 86 nlmimage10 5b432db9
International/Other Brands
Ticlid (ROCHE PALO)
Categories
UNII
OM90ZUW7M1
CAS number
55142-85-3
Weight
Average: 263.786
Monoisotopic: 263.05354785
Chemical Formula
C14H14ClNS
InChI Key
PHWBOXQYWZNQIN-UHFFFAOYSA-N
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
IUPAC Name
5-[(2-chlorophenyl)methyl]-4H,5H,6H,7H-thieno[3,2-c]pyridine
SMILES
ClC1=CC=CC=C1CN1CCC2=C(C1)C=CS2

Pharmacology

Indication

Used in patients, who have had a stroke or stroke precursors and who cannot take aspirin or aspirin has not worked, to try to prevent another thrombotic stroke.

Associated Conditions
Pharmacodynamics

Ticlopidine is a prodrug that is metabolised to an as yet undetermined metabolite that acts as a platelet aggregation inhibitor. Inhibition of platelet aggregation causes a prolongation of bleeding time. In its prodrug form, ticlopidine has no significant in vitro activity at the concentrations attained in vivo.

Mechanism of action

The active metabolite of ticlopidine prevents binding of adenosine diphosphate (ADP) to its platelet receptor, impairing the ADP-mediated activation of the glycoprotein GPIIb/IIIa complex. It is proposed that the inhibition involves a defect in the mobilization from the storage sites of the platelet granules to the outer membrane. No direct interference occurs with the GPIIb/IIIa receptor. As the glycoprotein GPIIb/IIIa complex is the major receptor for fibrinogen, its impaired activation prevents fibrinogen binding to platelets and inhibits platelet aggregation. By blocking the amplification of platelet activation by released ADP, platelet aggregation induced by agonists other than ADP is also inhibited by the active metabolite of ticlopidine.

TargetActionsOrganism
AP2Y purinoceptor 12
antagonist
Human
Absorption

Absorption is greater than 80%. Food increases absorption by approximately 20%.

Volume of distribution

The volume of distribution was not quantified.

Protein binding

Binds reversibly (98%) to plasma proteins, mainly to serum albumin and lipoproteins. The binding to albumin and lipoproteins is nonsaturable over a wide concentration range. Ticlopidine also binds to alpha-1 acid glycoprotein (about 15% or less).

Metabolism

Ticlopidine is metabolized extensively by the liver with only trace amounts of intact drug detected. At least 20 metabolites have been identified.

Route of elimination

Ticlopidine is eliminated mostly in the urine (60%) and somewhat in the feces (23%).

Half life

Half-life following a single 250-mg dose is approximately 7.9 hours in subjects 20 to 43 years of age and 12.6 hours in subjects 65 to 76 years of age. With repeated dosing (250 mg twice a day), half-life is about 4 days in subjects 20 to 43 years of age and about 5 days in subjects 65 to 76 years of age.

Clearance

Ticlopidine clearance was not quantified, but clearance decreases with age.

Toxicity

Single oral doses of ticlopidine at 1600 mg/kg and 500 mg/kg were lethal to rats and mice, respectively. Symptoms of acute toxicity were GI hemorrhage, convulsions, hypothermia, dyspnea, loss of equilibrium and abnormal gait. The FDA label includes a black-box warning of neutropenia, aplastic anemia, thrombotic thrombocytopenia purpura, and agranulocytosis, so it is necessary to monitor patients' WBC and platelets when they are taking ticlopidine.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Ticlopidine Action PathwayDrug action
Ticlopidine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Ticlopidine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Ticlopidine.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be decreased when combined with Ticlopidine.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Ticlopidine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Ticlopidine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Ticlopidine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Ticlopidine.
6-Deoxyerythronolide BThe metabolism of Ticlopidine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Ticlopidine.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Ticlopidine.
Food Interactions
  • High fat meals will increase ticlopidine absorption. As well, food can help ticlopidine-induced stomach upset.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014353
KEGG Compound
C07140
PubChem Compound
5472
PubChem Substance
46504438
ChemSpider
5273
BindingDB
85509
ChEBI
9588
ChEMBL
CHEMBL833
Therapeutic Targets Database
DAP000723
PharmGKB
PA451686
HET
TIC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ticlopidine
ATC Codes
B01AC05 — Ticlopidine
AHFS Codes
  • 20:12.18 — Platelet Aggregation Inhibitors
PDB Entries
3kw4
FDA label
Download (916 KB)
MSDS
Download (106 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherHealthy Volunteers1
2CompletedTreatmentStable Angina (SA)1
3CompletedPreventionMyocardial Infarction / Stable Angina (SA)1
3CompletedPreventionPeripheral Arterial Disease (PAD)1
4CompletedBasic SciencePharmacodynamics / Pharmacokinetics1
4CompletedPreventionCerebral Infarctions / Strokes1
4CompletedTreatmentCoronary Artery Disease1

Pharmacoeconomics

Manufacturers
  • Roche palo alto llc
  • Actavis elizabeth llc
  • Apotex inc
  • Caraco pharmaceutical laboratories ltd
  • Genpharm inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
Packagers
  • Apotex Inc.
  • AQ Pharmaceuticals Inc.
  • Caraco Pharmaceutical Labs
  • Eon Labs
  • F Hoffmann-La Roche Ltd.
  • Major Pharmaceuticals
  • Mylan
  • Physicians Total Care Inc.
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
Dosage forms
FormRouteStrength
TabletOral250 mg
Tablet, coatedOral250 mg/1
Tablet, film coatedOral250 mg/1
Prices
Unit descriptionCostUnit
Ticlid 30 250 mg tablet Bottle87.36USD bottle
Ticlid 250 mg tablet2.61USD tablet
Ticlopidine HCl 250 mg tablet2.1USD tablet
Ticlopidine 250 mg tablet1.86USD tablet
Apo-Ticlopidine 250 mg Tablet0.72USD tablet
Mylan-Ticlopidine 250 mg Tablet0.72USD tablet
Novo-Ticlopidine 250 mg Tablet0.72USD tablet
Nu-Ticlopidine 250 mg Tablet0.72USD tablet
Sandoz Ticlopidine 250 mg Tablet0.72USD tablet
Ticlopidine 250 mg Tablet0.72USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)approx. 1 189°CFrom Remington: The Science and Practice of Pharmacy
water solubilityFreely solubleFrom Remington: The Science and Practice of Pharmacy
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0219 mg/mLALOGPS
logP4.25ALOGPS
logP4.2ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)7.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.33 m3·mol-1ChemAxon
Polarizability27.99 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9902
Blood Brain Barrier+0.9906
Caco-2 permeable+0.6062
P-glycoprotein substrateSubstrate0.6111
P-glycoprotein inhibitor IInhibitor0.8
P-glycoprotein inhibitor IIInhibitor0.8513
Renal organic cation transporterInhibitor0.8152
CYP450 2C9 substrateNon-substrate0.8234
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.5155
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.9209
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8808
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9666
Ames testNon AMES toxic0.6773
CarcinogenicityNon-carcinogens0.9414
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity2.2022 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6392
hERG inhibition (predictor II)Inhibitor0.6333
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0920000000-c7636201a8e44462782b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0910000000-b3c5107441452553bbfd
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-7c7761f0b2d5d40ea37b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0490000000-735d41d20acd9ef61b19
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0920000000-763ff4372c7d534b9aef
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fb9-0900000000-fdcbf528f5121fd88009
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0900000000-73f90678ec6b04c031d4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0900000000-76105662a3b90ad51ec0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0900000000-43073273096ebea8675e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0imi-0960000000-88ccc8c382cb1c0eaed1

Taxonomy

Description
This compound belongs to the class of organic compounds known as thienopyridines. These are heterocyclic compounds containing a thiophene ring fused to a pyridine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thienopyridines
Sub Class
Not Available
Direct Parent
Thienopyridines
Alternative Parents
Phenylmethylamines / Benzylamines / Chlorobenzenes / Aralkylamines / Pyridines and derivatives / Aryl chlorides / Thiophenes / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds
show 3 more
Substituents
Thienopyridine / Benzylamine / Phenylmethylamine / Chlorobenzene / Halobenzene / Aralkylamine / Benzenoid / Aryl chloride / Aryl halide / Pyridine
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monochlorobenzenes, thienopyridine (CHEBI:9588)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Required for normal platelet aggregation and blood coagulation.
Gene Name
P2RY12
Uniprot ID
Q9H244
Uniprot Name
P2Y purinoceptor 12
Molecular Weight
39438.355 Da
References
  1. Storey RF: The P2Y12 receptor as a therapeutic target in cardiovascular disease. Platelets. 2001 Jun;12(4):197-209. [PubMed:11454254]
  2. Boeynaems JM, van Giezen H, Savi P, Herbert JM: P2Y receptor antagonists in thrombosis. Curr Opin Investig Drugs. 2005 Mar;6(3):275-82. [PubMed:15816504]
  3. Gachet C: The platelet P2 receptors as molecular targets for old and new antiplatelet drugs. Pharmacol Ther. 2005 Nov;108(2):180-92. Epub 2005 Jun 13. [PubMed:15955565]
  4. Zhan C, Yang J, Dong XC, Wang YL: Molecular modeling of purinergic receptor P2Y12 and interaction with its antagonists. J Mol Graph Model. 2007 Jul;26(1):20-31. Epub 2006 Sep 26. [PubMed:17110146]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Details
1. Cytochrome P450 2C19
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Moderate to strong inhibition of 2C19.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Richter T, Murdter TE, Heinkele G, Pleiss J, Tatzel S, Schwab M, Eichelbaum M, Zanger UM: Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J Pharmacol Exp Ther. 2004 Jan;308(1):189-97. doi: 10.1124/jpet.103.056127. Epub 2003 Oct 16. [PubMed:14563790]
  3. Donahue SR, Flockhart DA, Abernethy DR, Ko JW: Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19. Clin Pharmacol Ther. 1997 Nov;62(5):572-7. doi: 10.1016/S0009-9236(97)90054-0. [PubMed:9390115]
  4. Donahue S, Flockhart DA, Abernethy DR: Ticlopidine inhibits phenytoin clearance. Clin Pharmacol Ther. 1999 Dec;66(6):563-8. doi: 10.1053/cp.1999.v66.103277001. [PubMed:10613611]
  5. Giancarlo GM, Venkatakrishnan K, Granda BW, von Moltke LL, Greenblatt DJ: Relative contributions of CYP2C9 and 2C19 to phenytoin 4-hydroxylation in vitro: inhibition by sulfaphenazole, omeprazole, and ticlopidine. Eur J Clin Pharmacol. 2001 Apr;57(1):31-6. [PubMed:11372587]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  7. Drug Interactions & Labeling - FDA [Link]
  8. Ticlopidine Hydrochloride - Drug Summary - PDR [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Moderate to strong inhibition of 2D6.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Richter T, Murdter TE, Heinkele G, Pleiss J, Tatzel S, Schwab M, Eichelbaum M, Zanger UM: Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J Pharmacol Exp Ther. 2004 Jan;308(1):189-97. doi: 10.1124/jpet.103.056127. Epub 2003 Oct 16. [PubMed:14563790]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Giancarlo GM, Venkatakrishnan K, Granda BW, von Moltke LL, Greenblatt DJ: Relative contributions of CYP2C9 and 2C19 to phenytoin 4-hydroxylation in vitro: inhibition by sulfaphenazole, omeprazole, and ticlopidine. Eur J Clin Pharmacol. 2001 Apr;57(1):31-6. [PubMed:11372587]
  2. Donahue SR, Flockhart DA, Abernethy DR, Ko JW: Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19. Clin Pharmacol Ther. 1997 Nov;62(5):572-7. doi: 10.1016/S0009-9236(97)90054-0. [PubMed:9390115]
  3. Yang SH, Cho YA, Choi JS: Effects of ticlopidine on pharmacokinetics of losartan and its main metabolite EXP-3174 in rats. Acta Pharmacol Sin. 2011 Jul;32(7):967-72. doi: 10.1038/aps.2011.32. Epub 2011 Jun 13. [PubMed:21666702]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Richter T, Murdter TE, Heinkele G, Pleiss J, Tatzel S, Schwab M, Eichelbaum M, Zanger UM: Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J Pharmacol Exp Ther. 2004 Jan;308(1):189-97. doi: 10.1124/jpet.103.056127. Epub 2003 Oct 16. [PubMed:14563790]
  2. Aleil B, Rochoux G, Monassier JP, Cazenave JP, Gachet C: Ticlopidine could be an alternative therapy in the case of pharmacological resistance to clopidogrel: a report of three cases. J Thromb Haemost. 2007 Apr;5(4):879-81. doi: 10.1111/j.1538-7836.2007.02338.x. [PubMed:17403206]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  4. Ko JW, Desta Z, Soukhova NV, Tracy T, Flockhart DA: In vitro inhibition of the cytochrome P450 (CYP450) system by the antiplatelet drug ticlopidine: potent effect on CYP2C19 and CYP2D6. Br J Clin Pharmacol. 2000 Apr;49(4):343-51. [PubMed:10759690]
  5. Flockhart Table - Indiana University [Link]
  6. Ticlopidine Hydrochloride - Drug Summary - PDR [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Details
9. Cytochrome P450 2B6
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
  2. Richter T, Murdter TE, Heinkele G, Pleiss J, Tatzel S, Schwab M, Eichelbaum M, Zanger UM: Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J Pharmacol Exp Ther. 2004 Jan;308(1):189-97. doi: 10.1124/jpet.103.056127. Epub 2003 Oct 16. [PubMed:14563790]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  4. Ticlopidine Hydrochloride - Drug Summary - PDR [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Ko JW, Desta Z, Soukhova NV, Tracy T, Flockhart DA: In vitro inhibition of the cytochrome P450 (CYP450) system by the antiplatelet drug ticlopidine: potent effect on CYP2C19 and CYP2D6. Br J Clin Pharmacol. 2000 Apr;49(4):343-51. [PubMed:10759690]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:24