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
Structure for Cangrelor (DB06441)
- 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.
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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AP2Y purinoceptor 12 inhibitorHumans - 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of bleeding can be increased when Abciximab is combined with Cangrelor. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Cangrelor is combined with Abrocitinib. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Cangrelor. Acemetacin The risk or severity of bleeding and hemorrhage can be increased when Cangrelor is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cangrelor is combined with Acenocoumarol. Acetylsalicylic acid Acetylsalicylic acid may increase the antiplatelet activities of Cangrelor. Albutrepenonacog alfa The therapeutic efficacy of Albutrepenonacog alfa can be decreased when used in combination with Cangrelor. Alclofenac The risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Cangrelor. Aldesleukin The risk or severity of bleeding can be increased when Cangrelor is combined with Aldesleukin. Alemtuzumab The risk or severity of bleeding can be increased when Cangrelor is combined with Alemtuzumab. 
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- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
Products
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Ingredient UNII CAS InChI Key Cangrelor tetrasodium 2144G00Y7W 163706-36-3 COWWROCHWNGJHQ-OPKBHZIBSA-J - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Kengreal Injection, powder, lyophilized, for solution 50 mg/1 Intravenous The Medicines Company 2015-07-08 2019-02-28 US 
Kengreal Injection, powder, lyophilized, for solution 50 mg/1 Intravenous Chiesi USA, Inc. 2015-07-08 Not applicable US Kengrexal Injection, powder, for solution 50 mg Intravenous Chiesi Farmaceutici S.P.A. 2016-09-08 Not applicable EU 
Kengrexal Powder, for solution 50 mg / vial Intravenous Chiesi Farmaceutici S.P.A. Not applicable Not applicable Canada 
Categories
- ATC Codes
- B01AC25 — Cangrelor
- Drug Categories
- Adenine Nucleotides
- Anticoagulants
- Antiplatelet agents
- Blood and Blood Forming Organs
- Decreased Platelet Aggregation
- Hematologic Agents
- Heterocyclic Compounds, Fused-Ring
- Neurotransmitter Agents
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleotides
- P2Y12 Platelet Inhibitor
- Platelet Aggregation Inhibitors Excl. Heparin
- Purine Nucleotides
- Purinergic Agents
- Purinergic Antagonists
- Purinergic P2 Receptor Antagonists
- Purinergic P2Y Receptor Antagonists
- Purines
- Ribonucleotides
- 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
- Keating GM: Cangrelor: A Review in Percutaneous Coronary Intervention. Drugs. 2015 Aug;75(12):1425-34. doi: 10.1007/s40265-015-0445-3. [Article]
- Fugate SE, Cudd LA: Cangrelor for treatment of coronary thrombosis. Ann Pharmacother. 2006 May;40(5):925-30. Epub 2006 Apr 4. [Article]
- FDA Approved Drug Products: KENGREAL (cangrelor) injection [Link]
- External Links
- KEGG Drug
- D03359
- PubChem Compound
- 9854012
- PubChem Substance
- 310264872
- ChemSpider
- 8029718
- BindingDB
- 50118225
- 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intravenous 50 mg/1 Injection, powder, for solution Intravenous 50 mg Powder Intravenous; Parenteral 50 MG Powder, for solution Intravenous 50 mg / vial Injection 50 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6130208 No 2000-10-10 2018-06-29 US US6114313 No 2000-09-05 2017-12-11 US US8680052 No 2014-03-25 2033-03-09 US US8759316 No 2014-06-24 2029-05-13 US US9295687 No 2016-03-29 2035-07-10 US US9439921 No 2016-09-13 2035-07-10 US US9427448 No 2016-08-30 2030-11-10 US US9700575 No 2017-07-11 2035-07-10 US US9925265 No 2018-03-27 2029-05-13 US US10039780 No 2018-08-07 2035-07-10 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.33 mg/mL ALOGPS logP 1.21 ALOGPS logP -0.12 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 0.8 Chemaxon pKa (Strongest Basic) 2.61 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 7 Chemaxon Polar Surface Area 255.91 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 153.78 m3·mol-1 Chemaxon Polarizability 63.92 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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