Identification

Name
Prasugrel
Accession Number
DB06209
Description

Prasugrel, a thienopyridine derivative, is a platelet activation and aggregation inhibitor structurally and pharmacologically related to clopidogrel and ticlopidine. Similar to clopidogrel, prasugrel is a prodrug that requires enzymatic transformation in the liver to its active metabolite, R-138727. R-138727 irreversibly binds to P2Y12 type ADP receptors on platelets thus preventing activation of the GPIIb/IIIa receptor complex. As a result, inhibition of ADP-mediated platelet activation and aggregation occurs. Prasugrel was developed by Daiichi Sankyo Co. and is currently marketed in the United States and Canada in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). FDA approved in 2009.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 373.441
Monoisotopic: 373.114792406
Chemical Formula
C20H20FNO3S
Synonyms
  • Prasugrel
External IDs
  • CS-747
  • LY-640315

Pharmacology

Indication

Indicated in combination with acetylsalicylic acid (ASA) to prevent atherothrombotic events in patients with acute coronary syndrome (ACS) who are to be managed with percutaneous coronary intervention (PCI). May be used in patients with unstable angina (UA), non-ST elevation myocardial infarction (NSTEMI), ST-elevation myocardial infarction (STEMI) who are to be managed with PCI. Prasugrel is not recommended in patients 75 years of age or greater, those that weigh<60kg, and patients with a history of stroke or transient ischemic attack due to increased risk of fatal and intracranial bleeding.

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

Prasugrel is a thienopyridine ADP receptor inhibitors which inhibits platelet aggregation by irreversibly binding to P2Y12 receptors.

Mechanism of action

Prasugrel is an thienopyridine and a prodrug which inhibits ADP receptors by irreversibly acting on the P2Y12 receptor on platelets. The active metabolite of prasugrel prevents binding of adenosine diphosphate (ADP) to its platelet receptor, impairing the ADP-mediated activation of the glycoprotein GPIIb/IIIa complex. Prasugrel is proposed to have a similar mechanism of action to clopidogrel.

TargetActionsOrganism
AP2Y purinoceptor 12
antagonist
Humans
Absorption

79% or greater of the dose is absorbed after oral administration. Absorption and metabolism occur rapidly and peak plasma concentrations (Cmax) are reached approximately 30 minutes following oral administration. Administration with a high fat, high calorie meal did not affect the AUC of the active metabolite in healthy individuals, but the Cmax was decreased by ~49% and the Tmax was increased to 0.5 to 1.5 hours. Prasugrel may be administered with or without food.

Volume of distribution

44-68L

Protein binding

Approximately 98% of the active metabolite was bound to human serum albumin in a 4% buffered solution. The major inactive metabolites are also highly bound to human plasma proteins.

Metabolism

Prasugrel is not detected in plasma following oral administration. It is rapidly hydrolyzed in the intestine to thiolactone by human carboxylesterase (hCE) 2. This intermediate is further metabolized to its active metabolite, R-138727, in a single step by cytochrome P450 enzymes in the liver (primarily CYP3A4 and CYP2B6 and to a lesser extent by CYP2C9 and CYP2C19). The active metabolite is further metabolized by S-methylation or cysteine conjugation to two inactive metabolites.

Unlike clopidogrel, transformation of prasugrel to its active metabolite does not appear to be affected by cytochrome P450 polymorphisms.

Hover over products below to view reaction partners

Route of elimination

Approximately 68% of the orally administered dose is excreted in urine and 27% in the feces, as inactive metabolites. The active metabolite is not expected to be removed by dialysis.

Half-life

The active metabolite has an elimination half-life of about 7.4 hours (range 2-15 hours).

Clearance

Apparent clearance = 112 - 166 L/hr

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

LD50 (rat) 1,000 - 2,000 mg/kg; LD50 (rabbit) > 1,000 mg/kg

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
AbacavirAbacavir may decrease the excretion rate of Prasugrel which could result in a higher serum level.
AbametapirThe serum concentration of Prasugrel can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Prasugrel can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Prasugrel.
AbirateroneThe metabolism of Prasugrel can be decreased when combined with Abiraterone.
AcarboseAcarbose may decrease the excretion rate of Prasugrel which could result in a higher serum level.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Prasugrel.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Acemetacin is combined with Prasugrel.
AcenocoumarolThe risk or severity of bleeding can be increased when Prasugrel is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Prasugrel which could result in a higher serum level.
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 herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
  • Take with or without food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Prasugrel hydrochlorideG89JQ59I13389574-19-0JALHGCPDPSNJNY-UHFFFAOYSA-N
Product Images
International/Other Brands
Prasita (Daiichi Sankyo Co.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EffientTablet, film coated5 mg/1OralEli Lilly and Company2009-07-10Not applicableUs
EffientTablet, film coated10 mg/1OralPhysicians Total Care, Inc.2011-03-15Not applicableUs
EffientTablet10 mgOralEli Lilly & Co. Ltd.2010-05-172020-02-10Canada
EffientTablet, film coated10 mg/1OralEli Lilly and Company2009-07-102009-07-10Us
EffientTablet, film coated10 mg/1OralCardinal Health2012-03-012018-04-30Us55154 183120180907 15195 u9fi2d
EffientTablet, film coated5 mg/1OralEli Lilly and Company2009-07-102009-07-10Us
EffientTablet, film coated10 mg/1OralEli Lilly and Company2009-07-10Not applicableUs00002 5123 30 nlmimage10 e848f457
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe, Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe, Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe, Gmb H2009-02-23Not applicableEu
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
Jamp PrasugrelTablet10 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
PrasugrelTablet, film coated10 mg/1OralGolden State Medical Supply2017-10-16Not applicableUs
PrasugrelTablet, film coated10 mg/1OralAscend Laboratories, LLC2017-10-17Not applicableUs
PrasugrelTablet, film coated5 mg/1OralMylan Pharmaceuticals Inc.2017-08-15Not applicableUs
PrasugrelTablet, film coated5 mg/1OralPrasco Laboratories2017-08-152018-12-31Us
PrasugrelTablet, film coated10 mg/1OralApotex Corporation2017-10-16Not applicableUs
PrasugrelTablet, film coated5 mg/1OralPanacea Biotec Ltd.2017-10-16Not applicableUs
PrasugrelTablet, film coated10 mg/1OralA-S Medication Solutions2018-06-22Not applicableUs
PrasugrelTablet, film coated10 mg/1OralAccord Healthcare Inc.2019-01-16Not applicableUs
PrasugrelTablet, film coated10 mg/1OralAmneal Pharmaceuticals LLC2018-06-22Not applicableUs
Additional Data Available
  • Application Number
    Application Number

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

    Learn more
  • Product Code
    Product Code

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

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Categories

ATC Codes
B01AC22 — Prasugrel
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2,3,5-trisubstituted thiophenes / Aralkylamines / Fluorobenzenes / Pyridines and derivatives / Aryl fluorides / Alpha-amino ketones / Heteroaromatic compounds / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives
show 6 more
Substituents
2,3,5-trisubstituted thiophene / Alpha-aminoketone / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, acetate ester, cyclopropanes, ketone, monofluorobenzenes, thienopyridine (CHEBI:87723)

Chemical Identifiers

UNII
34K66TBT99
CAS number
150322-43-3
InChI Key
DTGLZDAWLRGWQN-UHFFFAOYSA-N
InChI
InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3
IUPAC Name
5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate
SMILES
CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1

References

Synthesis Reference

Teruhiko Inoue, Kazuyoshi Nakamura, Masahiko Hagihara, Hiroyuki Miyata, Yukinori Wada, Naoyuki Yokota, "Process for Producing High-Purity Prasugrel and Acid Addition Salt Thereof." U.S. Patent US20090203729, issued August 13, 2009.

US20090203729
General References
  1. Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [PubMed:18485086]
  2. Tagarakis GI: Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents. Recent Pat Cardiovasc Drug Discov. 2010 Nov;5(3):208-11. [PubMed:20874669]
  3. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110]
  4. Jeong YH, Tantry US, Gurbel PA: Importance of potent P2Y(12) receptor blockade in acute myocardial infarction: focus on prasugrel. Expert Opin Pharmacother. 2012 Aug;13(12):1771-96. doi: 10.1517/14656566.2012.704909. Epub 2012 Jul 12. [PubMed:22783896]
Human Metabolome Database
HMDB0015625
KEGG Drug
D05597
PubChem Compound
6918456
PubChem Substance
99443238
ChemSpider
5293653
RxNav
613391
ChEBI
87723
ChEMBL
CHEMBL1201772
PharmGKB
PA154410481
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Prasugrel
AHFS Codes
  • 20:12.18 — Platelet Aggregation Inhibitors
FDA label
Download (1000 KB)
MSDS
Download (134 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingNot AvailableAcute Coronary Syndromes (ACS)1
4Active Not RecruitingTreatmentAcute Coronary Syndromes (ACS)3
4Active Not RecruitingTreatmentCardiovascular Heart Disease1
4Active Not RecruitingTreatmentMyocardial Infarction2
4Active Not RecruitingTreatmentNon ST Segment Elevation Acute Coronary Syndrome / Non-ST-Elevation Myocardial Infarction / Unstable Angina Pectoris1
4CompletedNot AvailableCoronary Artery Disease (CAD)1
4CompletedBasic ScienceCoronary Artery Disease (CAD)1
4CompletedDiagnosticCoronary Artery Disease (CAD)1
4CompletedSupportive CareAcute Coronary Syndromes (ACS) / Platelet Function1
4CompletedTreatmentAcute Coronary Syndromes (ACS)6

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral10 mg
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral10 mg
Tablet, film coatedOral5 mg
Tablet, film coatedOral5 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6693115No2004-02-172021-07-03Us
CA2077695No2002-08-202012-09-08Canada
US8404703Yes2013-03-262023-07-02Us
US8569325Yes2013-10-292023-07-02Us
US5288726Yes1994-02-222017-10-14Us
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
logP3.536MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.00237 mg/mLALOGPS
logP3.67ALOGPS
logP4.31ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.81 m3·mol-1ChemAxon
Polarizability37.7 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9352
Caco-2 permeable+0.5325
P-glycoprotein substrateSubstrate0.767
P-glycoprotein inhibitor IInhibitor0.6555
P-glycoprotein inhibitor IINon-inhibitor0.7365
Renal organic cation transporterInhibitor0.5312
CYP450 2C9 substrateNon-substrate0.7508
CYP450 2D6 substrateNon-substrate0.7371
CYP450 3A4 substrateSubstrate0.5402
CYP450 1A2 substrateNon-inhibitor0.5288
CYP450 2C9 inhibitorNon-inhibitor0.5706
CYP450 2D6 inhibitorNon-inhibitor0.7051
CYP450 2C19 inhibitorInhibitor0.7083
CYP450 3A4 inhibitorNon-inhibitor0.7432
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8719
Ames testNon AMES toxic0.6616
CarcinogenicityNon-carcinogens0.9521
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.4834 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7927
hERG inhibition (predictor II)Non-inhibitor0.6438
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056s-2945000000-7653802e8e3994dc55bc

Targets

Kind
Protein
Organism
Humans
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. Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [PubMed:18485086]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Methylumbelliferyl-acetate deacetylase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and ...
Gene Name
CES2
Uniprot ID
O00748
Uniprot Name
Cocaine esterase
Molecular Weight
61806.41 Da
References
  1. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
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. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110]
  2. Dean L: Prasugrel Therapy and CYP Genotype . [PubMed:28520385]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
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. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110]
  2. Prasugrel FDA Label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
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. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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

Drug created on March 19, 2008 10:17 / Updated on August 04, 2020 17:12

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