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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21Cl2F3N5O12P3S2.4Na
Molecular Weight 864.287
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CANGRELOR TETRASODIUM

SMILES

[Na+].[Na+].[Na+].[Na+].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

InChI

InChIKey=COWWROCHWNGJHQ-OPKBHZIBSA-J
InChI=1S/C17H25Cl2F3N5O12P3S2.4Na/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);;;;/q;4*+1/p-4/t8-,10-,11-,14-;;;;/m1..../s1

HIDE SMILES / InChI
Cangrelor is a P2Y12 inhibitor that has been approved as an antiplatelet drug. It is marketed in the US under the brand name Kengreal and in Europe as Kengrexal. Cangrelor is an intravenous, direct-acting reversible P2Y12 inhibitor for patients undergoing percutaneous coronary intervention.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9H244
Gene ID: 64805.0
Gene Symbol: P2RY12
Target Organism: Homo sapiens (Human)
0.4 nM [IC50]
Target ID: Q09QM4
Gene ID: 767613.0
Gene Symbol: Gpr17
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
KENGREAL

Approved Use

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 [see Clinical Studies ( 14.1 )

Launch Date

2015
Preventing
KENGREAL

Approved Use

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 [see Clinical Studies ( 14.1 )

Launch Date

2015
Primary
KENGREAL

Approved Use

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 [see Clinical Studies ( 14.1 )

Launch Date

2015
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
299 ng/mL
135 μg/kg other, intravenous
dose: 135 μg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CANGRELOR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
635 ng/mL
270 μg/kg other, intravenous
dose: 270 μg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CANGRELOR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
249 ng × h/mL
135 μg/kg other, intravenous
dose: 135 μg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CANGRELOR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
478 ng × h/mL
270 μg/kg other, intravenous
dose: 270 μg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CANGRELOR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.61 min
135 μg/kg other, intravenous
dose: 135 μg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CANGRELOR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.71 min
270 μg/kg other, intravenous
dose: 270 μg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CANGRELOR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
unknown, intravenous
CANGRELOR plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 ug/kg single, intravenous
Overdose
Dose: 300 ug/kg
Route: intravenous
Route: single
Dose: 300 ug/kg
Sources:
unhealthy
n = 3
Health Status: unhealthy
Population Size: 3
Sources:
12 ug/kg/min single, intravenous
Overdose
Dose: 12 ug/kg/min
Route: intravenous
Route: single
Dose: 12 ug/kg/min
Sources:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
30 ug/kg single, intravenous
Recommended
Dose: 30 ug/kg
Route: intravenous
Route: single
Dose: 30 ug/kg
Sources:
unhealthy
n = 5529
Health Status: unhealthy
Sex: M+F
Population Size: 5529
Sources:
Disc. AE: Bleeding, Coronary artery dissection...
AEs leading to
discontinuation/dose reduction:
Bleeding (0.3%)
Coronary artery dissection (0.6%)
Coronary artery perforation (0.6%)
Dyspnea (0.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Bleeding 0.3%
Disc. AE
30 ug/kg single, intravenous
Recommended
Dose: 30 ug/kg
Route: intravenous
Route: single
Dose: 30 ug/kg
Sources:
unhealthy
n = 5529
Health Status: unhealthy
Sex: M+F
Population Size: 5529
Sources:
Coronary artery dissection 0.6%
Disc. AE
30 ug/kg single, intravenous
Recommended
Dose: 30 ug/kg
Route: intravenous
Route: single
Dose: 30 ug/kg
Sources:
unhealthy
n = 5529
Health Status: unhealthy
Sex: M+F
Population Size: 5529
Sources:
Coronary artery perforation 0.6%
Disc. AE
30 ug/kg single, intravenous
Recommended
Dose: 30 ug/kg
Route: intravenous
Route: single
Dose: 30 ug/kg
Sources:
unhealthy
n = 5529
Health Status: unhealthy
Sex: M+F
Population Size: 5529
Sources:
Dyspnea 0.6%
Disc. AE
30 ug/kg single, intravenous
Recommended
Dose: 30 ug/kg
Route: intravenous
Route: single
Dose: 30 ug/kg
Sources:
unhealthy
n = 5529
Health Status: unhealthy
Sex: M+F
Population Size: 5529
Sources:
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 58 uM]
no [IC50 58 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no
no
weak
weak
yes
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
The medicinal chemistry of the P2 receptor family.
2001
Blockade of adenosine diphosphate receptors P2Y(12) and P2Y(1) is required to inhibit platelet aggregation in whole blood under flow.
2001 Dec 1
Cangrelor AstraZeneca.
2001 Feb
Activation of Gi-coupled receptors releases a tonic state of inhibited platelet aggregation.
2001 Mar
A Gi-dependent pathway is required for activation of the small GTPase Rap1B in human platelets.
2002 Apr 5
Safety profile and tolerability of intravenous AR-C69931MX, a new antiplatelet drug, in unstable angina pectoris and non-Q-wave myocardial infarction.
2002 May
Effects of the NHE-1 inhibitor cariporide alone or together with the P2Y12 antagonist AR-C 69331 MX on CD62p expression and formation of platelet-leukocyte aggregates.
2003
Blockade of the platelet P2Y12 receptor by AR-C69931MX sustains coronary artery recanalization and improves the myocardial tissue perfusion in a canine thrombosis model.
2003 Feb 1
Advantages of fast-acting ADP receptor blockade in ischemic heart disease.
2003 Feb 1
A selective role for phosphatidylinositol 3,4,5-trisphosphate in the Gi-dependent activation of platelet Rap1B.
2003 Jan 3
Effects of inhibition of P2Y(1) and P2Y(12) on whole blood clotting, coagulum elasticity and fibrinolysis resistance studied with free oscillation rheometry.
2003 Mar 15
Agonist concentration-dependent differential responsivity of a human platelet purinergic receptor: pharmacological and kinetic studies of aggregation, deaggregation and shape change responses mediated by the purinergic P2Y1 receptor in vitro.
2003 Nov-Dec
Potential value of triple antiplatelet therapy for secondary stroke prevention.
2003 Oct
Preclinical and clinical studies with selective reversible direct P2Y12 antagonists.
2005 Apr
P2Y12 receptors play a significant role in the development of platelet microaggregation in patients with diabetes.
2005 Feb
Evidence that the purinergic receptor P2Y12 potentiates platelet shape change by a Rho kinase-dependent mechanism.
2005 Nov
Therapeutic goals for effective platelet inhibition: a consensus document.
2006 Fall
ADP receptors: inhibitory strategies for antiplatelet therapy.
2006 Jun
Critical role of ADP interaction with P2Y12 receptor in the maintenance of alpha(IIb)beta3 activation: association with Rap1B activation.
2006 Jun
Seven Golden Rules for heuristic filtering of molecular formulas obtained by accurate mass spectrometry.
2007 Mar 27
Clinical overview of promising nonthienopyridine antiplatelet agents.
2008 Aug
Survival of heparins, oral anticoagulants, and aspirin after the year 2010.
2008 Feb
Modulation of platelet and leucocyte function by a Chinese herbal formulation as compared with conventional antiplatelet agents.
2008 Feb
Changing trends in anti-coagulant therapies. Are heparins and oral anti-coagulants challenged?
2008 Jun
Acyl derivatives of coenzyme A inhibit platelet function via antagonism at P2Y1 and P2Y12 receptors: a new finding that may influence the design of anti-thrombotic agents.
2008 Mar
The active metabolite of prasugrel effectively blocks the platelet P2Y12 receptor and inhibits procoagulant and pro-inflammatory platelet responses.
2008 Mar
Antiplatelet therapy for secondary prevention of noncardioembolic ischemic stroke: a critical review.
2008 May
Patents

Sample Use Guides

Cangrelor is the active ingredient in KENGREAL which is administered at 30 micro-g/kg as an intravenous bolus prior to PCI and followed immediately by a 4 micro-g/kg/min IV infusion for at least 2 hours or duration of the procedure, whichever is longer.
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: referenced study was conducted on rat
Primary OPCs were isolated from mixed glial cultures from postnatal day 2 Sprague-Dawley rat cortex. Cells were suspended in NM15 Medium containing MEM, 15% heat-inactivated fetal bovine serum, 6 mg/mL glucose, 100 U/mL penicillin, 100 micro-g/mL streptomycin, 5 micro-g/mL insulin, and incubated at room Temperature in a RAN2-Ab-precoated plate. After 20 min, floating cells were transferred to a second RAN2-Ab-precoated plate and incubated for additional 20 min at RT. To verify whether OPCs can generate neurons under a standard protocol of oligodendrocyte differentiation, cells were plated in Neurobasal medium with 2 % B27 Supplement, 2 mM L-glutamine, 10 ng/ml human platelet-derived growth factor-BB, and 10 ng/ml human basic fibroblast growth factor to promote proliferation. After 2 days, OPCs were shifted to differentiating medium, and either grown under control conditions or exposed to the anticonvulsant agent valproic acid (VPA, 500 micro-M) for 24–72 h, fixed, and immunostained for GPR17 and the neuronal marker βIII-tubulin. The GPR17 antagonist Cangrelor (10 micro-M) was used in parallel to VPS (500 micro-M). The percentage of GPR17/βIII-tub double-positive cells over the total cell population increased in cultures treated with either Cangrelor or VPA. It was also observed that in Cangralor treated cells the percentage of NG2/GPR17 double-positive cells calculated on the total number of cells decreased, indicating that a subset of OPCs is shifting its fate from oligodendrocytes to neurons.
Name Type Language
CANGRELOR TETRASODIUM
MART.   USAN   WHO-DD  
USAN  
Official Name English
CANGRELOR TETRASODIUM [MART.]
Common Name English
CANGRELOR TETRASODIUM SALT [MI]
Common Name English
Cangrelor tetrasodium [WHO-DD]
Common Name English
AR-C69931MX
Code English
CANGRELOR TETRASODIUM SALT
MI  
Common Name English
CANGRELOR TETRASODIUM [USAN]
Common Name English
KENGREXAL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
EMA ASSESSMENT REPORTS KENGREXAL (AUTHORIZED: VASCULAR SURGICAR PROCEDURES
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
EMA ASSESSMENT REPORTS KENGREXAL (AUTHORIZED: ACUTE CORONARY SYNDROME)
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
Code System Code Type Description
SMS_ID
100000168765
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
DRUG BANK
DBSALT001292
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
RXCUI
1656051
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY RxNorm
PUBCHEM
10260031
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
CAS
163706-36-3
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
USAN
RR-129
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
FDA UNII
2144G00Y7W
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
NCI_THESAURUS
C76396
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL334966
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
MERCK INDEX
m3019
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID50167652
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY
EVMPD
SUB182388
Created by admin on Fri Dec 15 15:48:45 GMT 2023 , Edited by admin on Fri Dec 15 15:48:45 GMT 2023
PRIMARY