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    Chemistry

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    Also known as: 163706-06-7, Kengreal, Cangrelor free acid, Ar-c69931xx, Chembl334966, 6aq1y404u7
    Molecular Formula
    C17H25Cl2F3N5O12P3S2
    Molecular Weight
    776.4  g/mol
    InChI Key
    PAEBIVWUMLRPSK-IDTAVKCVSA-N
    FDA UNII
    6AQ1Y404U7
    Cangrelor
    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.
    Cangrelor is a P2Y12 Platelet Inhibitor. The mechanism of action of cangrelor is as a P2Y12 Receptor Antagonist. The physiologic effect of cangrelor is by means of Decreased Platelet Aggregation.
    1 2D Structure

    Cangrelor

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [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
    2.1.2 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
    2.1.3 InChI Key
    PAEBIVWUMLRPSK-IDTAVKCVSA-N
    2.1.4 Canonical SMILES
    CSCCNC1=C2C(=NC(=N1)SCCC(F)(F)F)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(C(P(=O)(O)O)(Cl)Cl)O)O)O
    2.1.5 Isomeric SMILES
    CSCCNC1=C2C(=NC(=N1)SCCC(F)(F)F)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(C(P(=O)(O)O)(Cl)Cl)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    6AQ1Y404U7
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ar C69931mx

    2. Ar-c69931mx

    3. Cangrelor Tetrasodium

    4. Kengreal

    5. N(6)-(2-methylthioethyl)-2-(3,3,3-trifluoropropylthio)-5'-adenylic Acid Monoanhydride With Dichloromethylenebis(phosphonic Acid)

    2.3.2 Depositor-Supplied Synonyms

    1. 163706-06-7

    2. Kengreal

    3. Cangrelor Free Acid

    4. Ar-c69931xx

    5. Chembl334966

    6. 6aq1y404u7

    7. 163706-06-7 (free Acid)

    8. (dichloro((((((2r,3s,4r,5r)-3,4-dihydroxy-5-(6-((2-(methylthio)ethyl)amino)-2-((3,3,3-trifluoropropyl)thio)-9h-purin-9-yl)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)methyl)phosphonic Acid

    9. [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

    10. (dichloromethylene)diphosphonic N-(2-(methylsulfanyl)ethyl)-2-((3,3,3-trifluoropropyl)sulfanyl-5'-adenylic Monoanhydride

    11. 5'-adenylicacid,n-[2-(methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]-,anhydridewithp,p'-(dichloromethylene)bis[phosphonicacid](1:1)

    12. Cangrelor [usan:inn:ban]

    13. Unii-6aq1y404u7

    14. Arl69931

    15. Cangrelor [inn]

    16. Cangrelor [mi]

    17. Cangrelor (usan/inn)

    18. Cangrelor [usan]

    19. Cangrelor [who-dd]

    20. Gtpl1776

    21. Schembl6113860

    22. Cangrelor [orange Book]

    23. Ammd00024

    24. Arl 69931mx

    25. Chebi:90841

    26. Hsdb 8489

    27. Dtxsid90167651

    28. Ar-c-69931mx

    29. Bdbm50118225

    30. Mfcd09837758

    31. Zinc85537017

    32. Am85616

    33. Db06441

    34. Ncgc00480787-02

    35. 5'-o-[({[dichloro(phosphono)methyl](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]-n-[2-(methylsulfanyl)ethyl]-2-[(3,3,3-trifluoropropyl)sulfanyl]adenosine

    36. Ac-28809

    37. Hy-19638

    38. Cs-0016143

    39. D03359

    40. Q3655338

    41. 5'-adenylic Acid, N-(2-(methylthio)ethyl)-2-((3,3,3-trifluoropropyl)thio)-, Monoanhydride With (dichloromethylene)bis(phosphonic Acid)

    42. 5'-adenylicacid, N-(2-(methylthio)ethyl)-2-((3,3,3-trifluoropropyl)thio)-, Monoanhydride With (dichloromethylene)bis(phosphonic Acid)

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 776.4 g/mol
    Molecular Formula C17H25Cl2F3N5O12P3S2
    XLogP3-1
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count21
    Rotatable Bond Count15
    Exact Mass774.9483145 g/mol
    Monoisotopic Mass774.9483145 g/mol
    Topological Polar Surface Area307 Ų
    Heavy Atom Count44
    Formal Charge0
    Complexity1140
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Platelet Aggregation Inhibitors; Purinergic P2Y Receptor Antagonists

    National Library of Medicine's Medical Subject Headings. Cangrelor. Online file (MeSH, 2018). Available from, as of November 8, 2018: https://meshb.nlm.nih.gov/search

    /CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Cangrelor is included in the database.

    NIH/NLM; ClinicalTrials.Gov. Available from, as of November 8, 2018: https://clinicaltrials.gov/

    Kengreal is indicated as an adjunct to percutaneous coronary intervention (PCI) to reduce the risk of periprocedural myocardial infarction (MI), repeat coronary revascularization, and stent thrombosis (ST) in patients who have not been treated with a P2Y12 platelet inhibitor and are not being given a glycoprotein IIb/IIIa inhibitor. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Kengreal (Cangrelor Injection, Powder, Lyophilized, For Solution) (Updated: August 10, 2016). Available from, as of November 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=88b434fa-8891-4fd5-9d86-7ea64667c08f

    4.2 Drug Warning

    The most common adverse effect of cangrelor reported in clinical trials was bleeding. Cases of transient dyspnea were also reported during clinical trials.

    American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018, p. 1661

    Hypersensitivity reactions (e.g., anaphylaxis, bronchospasm, angioedema, stridor) have been reported with cangrelor therapy.

    American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018, p. 1660

    Like other antiplatelet agents, cangrelor increases the risk of bleeding, which may be serious. In the CHAMPION PHOENIX trial, bleeding events of all severities were somewhat more common with cangrelor than with clopidogrel. In clinical trials, bleeding events in patients receiving cangrelor were mild, generally consisting of hematoma, ecchymosis, and oozing at the puncture site. In the CHAMPION PHOENIX trial, the rate of severe bleeding (per the Global Use of Strategies to Open Occluded Coronary Arteries [GUSTO] criteria) was not substantially increased by cangrelor, although the rate of major bleeding according to more sensitive criteria (Acute Catheterization and Urgent Intervention Triage Strategy [ACUITY]) was substantially higher with cangrelor than with clopidogrel (4.3 versus 2.5%). The increase in major bleeding with the ACUITY criteria was attributable to a greater incidence of hematoma at the site of vascular access in patients receiving cangrelor.

    American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018, p. 1660

    Cangrelor should not be used in patients with substantial active bleeding. The antiplatelet effects of cangrelor are negligible 1 hour after discontinuance of the infusion.

    American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018, p. 1660

    For more Drug Warnings (Complete) data for Cangrelor (11 total), please visit the HSDB record page.

    4.3 Drug 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.

    FDA Label

    Kengrexal, co-administered with acetylsalicylic acid (ASA), is indicated for the reduction of thrombotic cardiovascular events in adult patients with coronary artery disease undergoing percutaneous coronary intervention (PCI) who have not received an oral P2Y12 inhibitor prior to the PCI procedure and in whom oral therapy with P2Y12 inhibitors is not feasible or desirable.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Platelet Aggregation Inhibitors

    Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

    Purinergic P2Y Receptor Antagonists

    Compounds that bind to and block the stimulation of PURINERGIC P2Y RECEPTORS. Included under this heading are antagonists for specific P2Y receptor subtypes. (See all compounds classified as Purinergic P2Y Receptor Antagonists.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    CANGRELOR
    5.2.2 FDA UNII
    6AQ1Y404U7
    5.2.3 Pharmacological Classes
    P2Y12 Platelet Inhibitor [EPC]; P2Y12 Receptor Antagonists [MoA]; Decreased Platelet Aggregation [PE]
    5.3 ATC Code

    B01

    B01AC25

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    B - Blood and blood forming organs

    B01 - Antithrombotic agents

    B01A - Antithrombotic agents

    B01AC - Platelet aggregation inhibitors excl. heparin

    B01AC25 - Cangrelor

    5.4 Absorption, Distribution and Excretion

    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.

    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.

    Clearance

    The mean clearance is about 43.2 L/h.

    /MILK/ It is not known whether Kengreal is excreted in human milk.

    NIH; DailyMed. Current Medication Information for Kengreal (Cangrelor Injection, Powder, Lyophilized, For Solution) (Updated: August 10, 2016). Available from, as of November 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=88b434fa-8891-4fd5-9d86-7ea64667c08f

    Following IV administration of 3(H) Kengreal 58% of radioactivity was recovered in urine. The remaining 35% of radioactivity was in feces, presumably following biliary excretion. The average elimination half-life of Kengreal is about 3-6 minutes.

    NIH; DailyMed. Current Medication Information for Kengreal (Cangrelor Injection, Powder, Lyophilized, For Solution) (Updated: August 10, 2016). Available from, as of November 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=88b434fa-8891-4fd5-9d86-7ea64667c08f

    In a study in healthy volunteers, Kengreal administration at a dose of 30 ug/kg bolus plus 4 mcg/kg/min showed a volume of distribution of 3.9 L. Plasma protein binding of Kengreal is about 97-98%.

    NIH; DailyMed. Current Medication Information for Kengreal (Cangrelor Injection, Powder, Lyophilized, For Solution) (Updated: August 10, 2016). Available from, as of November 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=88b434fa-8891-4fd5-9d86-7ea64667c08f

    5.5 Metabolism/Metabolites

    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.

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

    NIH; DailyMed. Current Medication Information for Kengreal (Cangrelor Injection, Powder, Lyophilized, For Solution) (Updated: August 10, 2016). Available from, as of November 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=88b434fa-8891-4fd5-9d86-7ea64667c08f

    5.6 Biological Half-Life

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

    Following IV administration of 3(H) Kengreal, ... elimination half-life of Kengreal is about 3-6 minutes.

    NIH; DailyMed. Current Medication Information for Kengreal (Cangrelor Injection, Powder, Lyophilized, For Solution) (Updated: August 10, 2016). Available from, as of November 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=88b434fa-8891-4fd5-9d86-7ea64667c08f

    5.7 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.

    Cangrelor is a direct P2Y12 platelet receptor inhibitor that blocks ADP-induced platelet activation and aggregation. Cangrelor binds selectively and reversibly to the P2Y12 receptor to prevent further signaling and platelet activation.

    NIH; DailyMed. Current Medication Information for Kengreal (Cangrelor Injection, Powder, Lyophilized, For Solution) (Updated: August 10, 2016). Available from, as of November 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=88b434fa-8891-4fd5-9d86-7ea64667c08f

    API Reference Price

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    ABOUT THIS PAGE

    Cangrelor Manufacturers

    A Cangrelor manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Cangrelor, including repackagers and relabelers. The FDA regulates Cangrelor manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Cangrelor API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Cangrelor manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Cangrelor Suppliers

    A Cangrelor supplier is an individual or a company that provides Cangrelor active pharmaceutical ingredient (API) or Cangrelor finished formulations upon request. The Cangrelor suppliers may include Cangrelor API manufacturers, exporters, distributors and traders.

    click here to find a list of Cangrelor suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Cangrelor USDMF

    A Cangrelor DMF (Drug Master File) is a document detailing the whole manufacturing process of Cangrelor active pharmaceutical ingredient (API) in detail. Different forms of Cangrelor DMFs exist exist since differing nations have different regulations, such as Cangrelor USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Cangrelor DMF submitted to regulatory agencies in the US is known as a USDMF. Cangrelor USDMF includes data on Cangrelor's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Cangrelor USDMF is kept confidential to protect the manufacturer’s intellectual property.

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    Cangrelor WC

    A Cangrelor written confirmation (Cangrelor WC) is an official document issued by a regulatory agency to a Cangrelor manufacturer, verifying that the manufacturing facility of a Cangrelor active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Cangrelor APIs or Cangrelor finished pharmaceutical products to another nation, regulatory agencies frequently require a Cangrelor WC (written confirmation) as part of the regulatory process.

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    Cangrelor NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Cangrelor as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Cangrelor API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Cangrelor as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Cangrelor and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Cangrelor NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Cangrelor suppliers with NDC on PharmaCompass.

    Cangrelor GMP

    Cangrelor Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Cangrelor GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Cangrelor GMP manufacturer or Cangrelor GMP API supplier for your needs.

    Cangrelor CoA

    A Cangrelor CoA (Certificate of Analysis) is a formal document that attests to Cangrelor's compliance with Cangrelor specifications and serves as a tool for batch-level quality control.

    Cangrelor CoA mostly includes findings from lab analyses of a specific batch. For each Cangrelor CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Cangrelor may be tested according to a variety of international standards, such as European Pharmacopoeia (Cangrelor EP), Cangrelor JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Cangrelor USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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