Identification

Summary

Cangrelor is a P2Y12 platelet receptor antagonist used during percutaneous coronary intervention to reduce the risk for periprocedural myocardial infarction (MI), repeat coronary revascularization, and stent thrombosis (ST).

Brand Names
Kengreal, Kengrexal
Generic Name
Cangrelor
DrugBank Accession Number
DB06441
Background

Cangrelor is an intravenous, direct-acting, reversible P2Y12 inhibitor for patients undergoing percutaneous coronary intervention (PCI) who have not been yet treated by oral P2Y12 inhibitors. An advantage Cangrelor provides over oral P2Y12 inhibitors (such as prasugrel, ticagrelor, and clopidogrel) is that it is an active drug not requiring metabolic conversion therefore providing a rapid onset and offset of action. Cangrelor was approved by the FDA in June 2015 for intravenous application.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 776.35
Monoisotopic: 774.9483145
Chemical Formula
C17H25Cl2F3N5O12P3S2
Synonyms
  • [dichloro-[[[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(2-methylsulfanylethylamino)-2-(3,3,3-trifluoropropylsulfanyl)purin-9-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]methyl]phosphonic acid
  • Cangrelor
External IDs
  • AR-C69931XX
  • AR69931

Pharmacology

Indication

For use as an adjunct to percutaneous coronary intervention (PCI) for reducing the risk of periprocedural myocardial infarction (MI), repeat coronary revascularization, and stent thrombosis (ST) in patients in who have not been treated with a P2Y12 platelet inhibitor and are not being given a glycoprotein IIb/IIIa inhibitor.

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action

Cangrelor is a selective, reversible, P2Y12 platelet receptor antagonist which inhibits ADP platelet aggregation. ADP is typically released by damaged blood vessels, red blood cells, and/or platelets due to agonists stimulating platelet activity. ADP binds to P2Y12 to stimulate and complete platelet aggregation by inhibiting adenylyl cyclase by a Gi protein, thus potentiating dense granule secretion and increasing coagulation activity. Cangrelor acts on the same target as oral irreversible inhibitors clopidogrel and ticlopidine and has a similar mechanism of action, but is reversible and provides a fast onset and offset of action.

TargetActionsOrganism
AP2Y purinoceptor 12
inhibitor
Humans
Absorption

Not Available

Volume of distribution

In a study in healthy volunteers administration at a dose of 30 mcg/kg bolus plus 4 mcg/kg/min showed a volume of distribution of 3.9 L.

Protein binding

about 97-98%.

Metabolism

Cangrelor is deactivated rapidly in the circulation by dephosphorylation to its primary metabolite, a nucleoside, which has negligible anti-platelet activity. Cangrelor's metabolism is independent of hepatic function and it does not interfere with other drugs metabolized by hepatic enzymes.

Route of elimination

Following IV administration of [3H] cangrelor, 58% of radioactivity was recovered in urine. The remaining 35% of radioactivity was in feces, presumably following biliary excretion.

Half-life

The average elimination half-life of cangrelor is about 3-6 minutes.

Clearance

The mean clearance is about 43.2 L/h.

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

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
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Cangrelor.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Cangrelor.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Cangrelor is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cangrelor is combined with Acenocoumarol.
Acetylsalicylic acidAcetylsalicylic acid may increase the antiplatelet activities of Cangrelor.
Albutrepenonacog alfaThe therapeutic efficacy of Albutrepenonacog alfa can be decreased when used in combination with Cangrelor.
AlclofenacThe risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Cangrelor.
AldesleukinThe risk or severity of bleeding can be increased when Cangrelor is combined with Aldesleukin.
AlemtuzumabThe risk or severity of bleeding can be increased when Cangrelor is combined with Alemtuzumab.
AlteplaseThe risk or severity of bleeding can be increased when Cangrelor is combined with Alteplase.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Cangrelor tetrasodium2144G00Y7W163706-36-3COWWROCHWNGJHQ-OPKBHZIBSA-J
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
KengrealInjection, powder, lyophilized, for solution50 mg/1IntravenousThe Medicines Company2015-07-082019-02-28US flag
KengrealInjection, powder, lyophilized, for solution50 mg/1IntravenousChiesi USA, Inc.2015-07-08Not applicableUS flag
KengrexalInjection, powder, for solution50 mgIntravenousChiesi Farmaceutici S.P.A.2016-09-08Not applicableEU flag

Categories

ATC Codes
B01AC25 — Cangrelor
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / 6-alkylaminopurines / Glycosylamines / Monosaccharide phosphates / Bisphosphonates / Alkylarylthioethers / Aminopyrimidines and derivatives / Secondary alkylarylamines / Monoalkyl phosphates / N-substituted imidazoles
show 18 more
Substituents
1,2-diol / 6-alkylaminopurine / 6-aminopurine / Alcohol / Alkyl chloride / Alkyl fluoride / Alkyl halide / Alkyl phosphate / Alkylarylthioether / Amine
show 46 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6AQ1Y404U7
CAS number
163706-06-7
InChI Key
PAEBIVWUMLRPSK-IDTAVKCVSA-N
InChI
InChI=1S/C17H25Cl2F3N5O12P3S2/c1-43-5-3-23-12-9-13(26-15(25-12)44-4-2-16(20,21)22)27(7-24-9)14-11(29)10(28)8(38-14)6-37-42(35,36)39-41(33,34)17(18,19)40(30,31)32/h7-8,10-11,14,28-29H,2-6H2,1H3,(H,33,34)(H,35,36)(H,23,25,26)(H2,30,31,32)/t8-,10-,11-,14-/m1/s1
IUPAC Name
[dichloro({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[2-(methylsulfanyl)ethyl]amino}-2-[(3,3,3-trifluoropropyl)sulfanyl]-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl})methyl]phosphonic acid
SMILES
CSCCNC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)C(Cl)(Cl)P(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC(SCCC(F)(F)F)=N1

References

General References
  1. Keating GM: Cangrelor: A Review in Percutaneous Coronary Intervention. Drugs. 2015 Aug;75(12):1425-34. doi: 10.1007/s40265-015-0445-3. [Article]
  2. Fugate SE, Cudd LA: Cangrelor for treatment of coronary thrombosis. Ann Pharmacother. 2006 May;40(5):925-30. Epub 2006 Apr 4. [Article]
  3. FDA Approved Drug Products: KENGREAL (cangrelor) injection [Link]
KEGG Drug
D03359
PubChem Compound
9854012
PubChem Substance
310264872
ChemSpider
8029718
BindingDB
50118225
RxNav
1656052
ChEBI
90841
ChEMBL
CHEMBL334966
ZINC
ZINC000085537017
PharmGKB
PA165945763
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cangrelor
FDA label
Download (520 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAcute Coronary Syndrome (ACS) / High On-treatment Platelet Reactivity (HTPR) / Microvascular Obstruction (MVO) / ST Segment Elevation Myocardial Infarction (STEMI) / Thrombolysis in Myocardial Infarction (TIMI) / Unstable Angina Pectoris1
4CompletedTreatmentCoronary Artery Disease (CAD) / ST Segment Elevation Myocardial Infarction (STEMI)1
4CompletedTreatmentPercutaneous Coronary Intervention (PCI) / ST Segment Elevation Myocardial Infarction (STEMI)1
4CompletedTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
4RecruitingTreatmentAcute Coronary Syndrome (ACS) / Cardiopulmonary Arrest With Successful Resuscitation / Hypothermia, Induced1
4RecruitingTreatmentAcute Coronary Syndrome (ACS) / Coronary Artery Disease (CAD)1
4RecruitingTreatmentAcute Coronary Syndrome (ACS) / Out-of-hospital Cardiac Arrest (OHCA)1
4RecruitingTreatmentAcute Myocardial Infarction (AMI) / Shock, Cardiogenic1
4RecruitingTreatmentCoronary Artery Disease (CAD)1
4RecruitingTreatmentST Segment Elevation Myocardial Infarction (STEMI)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous50 mg/1
Injection, powder, for solutionIntravenous50 mg
PowderIntravenous; Parenteral50 MG
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6130208No2000-10-102018-06-29US flag
US6114313No2000-09-052017-12-11US flag
US8680052No2014-03-252033-03-09US flag
US8759316No2014-06-242029-05-13US flag
US9295687No2016-03-292035-07-10US flag
US9439921No2016-09-132035-07-10US flag
US9427448No2016-08-302030-11-10US flag
US9700575No2017-07-112035-07-10US flag
US9925265No2018-03-272029-05-13US flag
US10039780No2018-08-072035-07-10US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.33 mg/mLALOGPS
logP1.21ALOGPS
logP-0.12ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.8ChemAxon
pKa (Strongest Basic)2.61ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area255.91 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity153.78 m3·mol-1ChemAxon
Polarizability63.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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. Gan XD, Wei BZ, Fang D, Fang Q, Li KY, Ding SL, Peng S, Wan J: Efficacy and safety analysis of new P2Y12 inhibitors versus clopidogrel in patients with percutaneous coronary intervention: a meta-analysis. Curr Med Res Opin. 2015 Dec;31(12):2313-23. doi: 10.1185/03007995.2015.1098600. Epub 2015 Nov 4. [Article]

Drug created at March 19, 2008 16:33 / Updated at August 07, 2021 00:11