Identification

Name
Ticagrelor
Accession Number
DB08816
Description

Ticagrelor, or AZD6140, was first described in the literature in 2003.4,5 Ticagrelor is an ADP derivative developed for its P2Y12 receptor antagonism.5 Unlike clopidogrel, ticagrelor is not a prodrug.5 It is marketed by Astra Zeneca as Brilinta in the US6 and Brilique or Possia in the EU,7.

Ticagrelor was granted EMA approval on 3 December 2010.7 Ticagrelor was granted FDA approval on 20 July 2011.6

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 522.568
Monoisotopic: 522.186080514
Chemical Formula
C23H28F2N6O4S
Synonyms
  • (1S,2S,3R,5S)-3-(7-((1R,2S)-2-(3,4-Difluorophenyl)cyclopropylamino)-5-(propylthio)-3H-(1,2,3)triazolo(4,5-d)pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
  • Ticagrelor
External IDs
  • AR-C126532XX
  • AZD 6140
  • AZD-6140
  • AZD6140

Pharmacology

Indication

Ticagrelor is indicated to reduce the risk of cardiovascular death, myocardial infarction, and stroke in patients with acute coronary syndrome or a history of myocardial infarction.6 Ticagrelor is also indicated to reduce the risk of a first myocardial infarction or stroke in high risk patients with coronary artery disease.6

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Ticagrelor is a P2Y12 receptor antagonist that inhibits the formation of thromboses to reduce the risk of myocardial infarction and ischemic stroke.1,3 It has a moderate duration of action as it is given twice daily, and a wide therapeutic index as high single doses are well tolerated.6,7 Patients should be counselled regarding the risk of bleeding, dyspnea, and bradyarrhythmias.6

Mechanism of action

Ticagrelor is a P2Y12 receptor antagonist.1

The P2Y12 receptor couples with Gαi2 and other Gi proteins which inhibit adenylyl cyclase.3 Gi mediated signalling also activates PI3K, Akt, Rap1b, and potassium channels.3 The downstream effects of these activities mediate hemostasis and lead to platelet aggregation.3

Antagonism of the P2Y12 receptor reduces development of occlusive thromboses, which can reduce the risk of myocardial infarction and ischemic stroke.3

TargetActionsOrganism
AP2Y purinoceptor 12
inhibitor
Humans
Absorption

Ticagrelor is 36% orally bioavailable.6 A single 200mg oral dose of ticagrelor reaches a Cmax of 923ng/mL, with a Tmax of 1.5 hours and an AUC of 6675ng*h/mL.1 The active metabolite of ticagrelor reaches a Cmax of 264ng/mL, with a Tmax of 3.0 hours and an AUC of 2538ng*h/mL.1

Volume of distribution

The steady state volume of distribution of ticagrelor is 88 L.6

Protein binding

Ticagrelor and its active metabolite ate >99% protein bound in plasma, particularly albumin.2,6

Metabolism

The complete structure of all ticagrelor metabolites are not well defined.1 Ticagrelor can be dealkylated at postition 5 of the cyclopentane ring to form the active AR-C124910XX.1 AR-C124910XX's cyclopentane ring can be further glucuronidated or the alkyl chain attached to the sulfur can be hydroxylated.1 Ticagrelor can also be glucuronidated or hydroxylated.1 Ticagrelor can also be N-dealkylated to form AR-C133913XX, which is further glucuronidated or hydroxylated.1

Hover over products below to view reaction partners

Route of elimination

A radiolabelled dose of ticagrelor is 57.8% recovered in feces and 26.5% recovered in urine.1,6 Less than 1% of the dose is recovered as the unmetabolized parent drug.6 The active metabolite AC-C124910XX makes up 21.7% of the recovery in the feces.1 The metabolite AR-C133913XX makes up 9.2% of the recovery in the urine and 2.7% of the recovery in the feces.1 Other minor metabolites are predominantly recovered in the urine.1

Half-life

Ticagrelor has a plasma half life of approximately 8 hours, while the active metabolite has a plasma half life of approximately 12 hours.1

Clearance

The renal clearance of ticagrelor is 0.00584L/h.1

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Patients experiencing an overdose may present with bleeding, nausea, vomiting, diarrhea, and ventricular pauses.6 Overdose can be managed through symptomatic and supportive treatment, including ECG monitoring.6,7 Dialysis is not expected to remove ticagrelor from the blood due to it being highly protein bound.6

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Ticagrelor can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Ticagrelor.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Ticagrelor.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Ticagrelor.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Ticagrelor.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Acemetacin is combined with Ticagrelor.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Ticagrelor.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Ticagrelor.
Acetylsalicylic acidThe therapeutic efficacy of Ticagrelor can be decreased when used in combination with Acetylsalicylic acid.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Ticagrelor.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid grapefruit products. Grapefruit inhibits the CYP3A4 metabolism of ticagrelor, which may increase its serum concentration.
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Herbs with antiplatelet activity may increase the risk of bleeding. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
  • Avoid St. John's Wort. This herb induces the CYP3A4 metabolism of ticagrelor and may reduce its serum concentration.
  • Take with or without food.

Products

Product Images
International/Other Brands
Brilinta / Possia (AstraZeneca)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BrilintaTablet90 mgOralAstra Zeneca2011-06-01Not applicableCanada flag
BrilintaTablet90 mg/1OralAstraZeneca Pharmaceuticals LP2011-08-05Not applicableUS flag00186 0777 60 nlmimage10 8639c32e
BrilintaTablet90 mg/1Oralbryant ranch prepack2011-08-052016-04-30US flag63629 529220180907 15195 loebzm
BrilintaTablet90 mg/1OralCardinal Health2011-08-05Not applicableUS flag55154 961820180907 15195 153xv46
BrilintaTablet60 mgOralAstra Zeneca2016-06-13Not applicableCanada flag
BrilintaTablet60 mg/1OralAstraZeneca Pharmaceuticals LP2015-09-04Not applicableUS flag
BriliqueTablet, film coated60 mgOralAstra Zeneca Ab2010-12-03Not applicableEU flag
BriliqueTablet, film coated60 mgOralAstra Zeneca Ab2010-12-03Not applicableEU flag
BriliqueTablet, film coated90 mgOralAstra Zeneca Ab2010-12-03Not applicableEU flag
BriliqueTablet, film coated90 mgOralAstra Zeneca Ab2010-12-03Not applicableEU flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NaTablet90 mg/1OralSunshine Lake Pharma Co., Ltd.2020-04-092020-04-10US flag
NaTablet60 mg/1OralSunshine Lake Pharma Co., Ltd.2020-04-092020-04-10US flag
TicagrelorTablet90 mg/1OralAmneal Pharmaceuticals NY LLC2019-01-23Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
B01AC24 — Ticagrelor
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Triazolopyrimidines
Sub Class
Not Available
Direct Parent
Triazolopyrimidines
Alternative Parents
Alkylarylthioethers / Aminopyrimidines and derivatives / Secondary alkylarylamines / Fluorobenzenes / Aryl fluorides / Cyclitols and derivatives / Cyclopentanols / Imidolactams / Triazoles / Heteroaromatic compounds
show 7 more
Substituents
1,2,3-triazole / Alcohol / Alkylarylthioether / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Aryl thioether / Azacycle
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, aryl sulfide, secondary amino compound, triazolopyrimidines, hydroxyether (CHEBI:68558)

Chemical Identifiers

UNII
GLH0314RVC
CAS number
274693-27-5
InChI Key
OEKWJQXRCDYSHL-FNOIDJSQSA-N
InChI
InChI=1S/C23H28F2N6O4S/c1-2-7-36-23-27-21(26-15-9-12(15)11-3-4-13(24)14(25)8-11)18-22(28-23)31(30-29-18)16-10-17(35-6-5-32)20(34)19(16)33/h3-4,8,12,15-17,19-20,32-34H,2,5-7,9-10H2,1H3,(H,26,27,28)/t12-,15+,16+,17-,19-,20+/m0/s1
IUPAC Name
(1S,2S,3R,5S)-3-(7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
SMILES
CCCSC1=NC2=C(N=NN2[[email protected]@H]2C[[email protected]](OCCO)[[email protected]@H](O)[[email protected]]2O)C(N[[email protected]@H]2C[[email protected]]2C2=CC(F)=C(F)C=C2)=N1

References

Synthesis Reference

Anil Shahaji Khile, "NOVEL PROCESSES FOR THE PREPARATION OF PHENYLCYCLOPROPYLAMINE DERIVATIVES AND USE THEREOF FOR PREPARING TICAGRELOR." U.S. Patent US20130165696, issued June 27, 2013.

US20130165696
General References
  1. Teng R, Oliver S, Hayes MA, Butler K: Absorption, distribution, metabolism, and excretion of ticagrelor in healthy subjects. Drug Metab Dispos. 2010 Sep;38(9):1514-21. doi: 10.1124/dmd.110.032250. Epub 2010 Jun 15. [PubMed:20551239]
  2. Angheloiu GO, Gugiu GB, Ruse C, Pandey R, Dasari RR, Whatling C: Ticagrelor Removal From Human Blood. JACC Basic Transl Sci. 2017 Apr 24;2(2):135-145. doi: 10.1016/j.jacbts.2017.01.007. eCollection 2017 Apr. [PubMed:30167561]
  3. Dorsam RT, Kunapuli SP: Central role of the P2Y12 receptor in platelet activation. J Clin Invest. 2004 Feb;113(3):340-5. doi: 10.1172/JCI20986. [PubMed:14755328]
  4. Jacobson KA, Costanzi S, Ohno M, Joshi BV, Besada P, Xu B, Tchilibon S: Molecular recognition at purine and pyrimidine nucleotide (P2) receptors. Curr Top Med Chem. 2004;4(8):805-19. doi: 10.2174/1568026043450961. [PubMed:15078212]
  5. Springthorpe B, Bailey A, Barton P, Birkinshaw TN, Bonnert RV, Brown RC, Chapman D, Dixon J, Guile SD, Humphries RG, Hunt SF, Ince F, Ingall AH, Kirk IP, Leeson PD, Leff P, Lewis RJ, Martin BP, McGinnity DF, Mortimore MP, Paine SW, Pairaudeau G, Patel A, Rigby AJ, Riley RJ, Teobald BJ, Tomlinson W, Webborn PJ, Willis PA: From ATP to AZD6140: the discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis. Bioorg Med Chem Lett. 2007 Nov 1;17(21):6013-8. Epub 2007 Aug 19. [PubMed:17827008]
  6. FDA Approved Drug Products: Brilinta Ticagrelor Oral Tablets [Link]
  7. EMA Summary of Product Characteristics: Brilique Ticagrelor Oral Tablet [Link]
Human Metabolome Database
HMDB0015702
KEGG Drug
D09017
PubChem Compound
9871419
PubChem Substance
175427101
ChemSpider
8047109
BindingDB
50397205
RxNav
1116632
ChEBI
68558
ChEMBL
CHEMBL398435
ZINC
ZINC000028957444
PharmGKB
PA165374673
PDBe Ligand
TIQ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ticagrelor
AHFS Codes
  • 20:12.18 — Platelet Aggregation Inhibitors
PDB Entries
5alb / 5alc
FDA label
Download (1.21 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingNot AvailableAcute Coronary Syndromes (ACS)1
4Active Not RecruitingTreatmentAcute Coronary Syndromes (ACS)1
4Active Not RecruitingTreatmentCoronary Artery Disease (CAD) / Type 2 Diabetes Mellitus1
4Active Not RecruitingTreatmentLOVASTATIN/TICAGRELOR [VA Drug Interaction]1
4Active Not RecruitingTreatmentMyocardial Infarction1
4Active Not RecruitingTreatmentNon ST Segment Elevation Acute Coronary Syndrome / Non-ST-Elevation Myocardial Infarction / Unstable Angina Pectoris1
4Active Not RecruitingTreatmentPercutaneous Coronary Intervention (PCI)1
4CompletedNot AvailableHealthy Volunteers1
4CompletedBasic ScienceAcute Coronary Syndromes (ACS) / Atrial Fibrillation (AF)1
4CompletedBasic ScienceCoronary Artery Disease (CAD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral60 mg
TabletOral90 mg
Tablet, coated60 mg
Tablet, coated90 mg
Tablet
Tablet, film coatedOral60 mg
Tablet, film coatedOral90 mg
Tablet, orally disintegratingOral90 MG
TabletOral60 mg/1
Tablet, coatedOral60 mg
Tablet, coatedOral90 mg
TabletOral90 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2296665No2008-06-102018-07-15Canada flag
CA2351709No2010-04-062019-12-02Canada flag
CA2408596No2010-12-212021-05-31Canada flag
US7265124No2007-09-042021-07-09US flag
US6525060No2003-02-252019-12-02US flag
US7250419No2007-07-312019-12-02US flag
US6251910No2001-06-262018-07-15US flag
US8425934No2013-04-232030-04-17US flag
USRE46276No2017-01-172019-12-02US flag
US10300065No2019-05-282036-01-27US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility10 μg/mLFDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.063 mg/mLALOGPS
logP2.31ALOGPS
logP2.28ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.94ChemAxon
pKa (Strongest Basic)1.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area138.44 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity142.13 m3·mol-1ChemAxon
Polarizability51.31 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.994
Blood Brain Barrier-0.6719
Caco-2 permeable-0.5989
P-glycoprotein substrateSubstrate0.7626
P-glycoprotein inhibitor INon-inhibitor0.5907
P-glycoprotein inhibitor IINon-inhibitor0.9617
Renal organic cation transporterNon-inhibitor0.8606
CYP450 2C9 substrateNon-substrate0.7734
CYP450 2D6 substrateNon-substrate0.8048
CYP450 3A4 substrateSubstrate0.5057
CYP450 1A2 substrateNon-inhibitor0.5372
CYP450 2C9 inhibitorNon-inhibitor0.5767
CYP450 2D6 inhibitorNon-inhibitor0.8016
CYP450 2C19 inhibitorNon-inhibitor0.6016
CYP450 3A4 inhibitorInhibitor0.8744
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6243
Ames testNon AMES toxic0.5075
CarcinogenicityNon-carcinogens0.7777
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6308 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7742
hERG inhibition (predictor II)Non-inhibitor0.5914
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

Targets

Details
1. P2Y purinoceptor 12
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
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. Teng R: Ticagrelor: Pharmacokinetic, Pharmacodynamic and Pharmacogenetic Profile: An Update. Clin Pharmacokinet. 2015 Nov;54(11):1125-38. doi: 10.1007/s40262-015-0290-2. [PubMed:26063049]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Teng R, Oliver S, Hayes MA, Butler K: Absorption, distribution, metabolism, and excretion of ticagrelor in healthy subjects. Drug Metab Dispos. 2010 Sep;38(9):1514-21. doi: 10.1124/dmd.110.032250. Epub 2010 Jun 15. [PubMed:20551239]
  2. FDA Approved Drug Products: Brilinta Ticagrelor Oral Tablets [Link]
Kind
Protein
Organism
Humans
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. Zhou D, Andersson TB, Grimm SW: In vitro evaluation of potential drug-drug interactions with ticagrelor: cytochrome P450 reaction phenotyping, inhibition, induction, and differential kinetics. Drug Metab Dispos. 2011 Apr;39(4):703-10. doi: 10.1124/dmd.110.037143. Epub 2010 Dec 22. [PubMed:21177984]
  2. Teng R: Ticagrelor: Pharmacokinetic, Pharmacodynamic and Pharmacogenetic Profile: An Update. Clin Pharmacokinet. 2015 Nov;54(11):1125-38. doi: 10.1007/s40262-015-0290-2. [PubMed:26063049]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Angheloiu GO, Gugiu GB, Ruse C, Pandey R, Dasari RR, Whatling C: Ticagrelor Removal From Human Blood. JACC Basic Transl Sci. 2017 Apr 24;2(2):135-145. doi: 10.1016/j.jacbts.2017.01.007. eCollection 2017 Apr. [PubMed:30167561]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA Approved Drug Products: Brilinta Ticagrelor Oral Tablets [Link]

Drug created on August 01, 2011 15:32 / Updated on September 20, 2020 08:50

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