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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H28F2N6O4S
Molecular Weight 522.568
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TICAGRELOR

SMILES

CCCSC1=NC2=C(N=NN2[C@@H]3C[C@H](OCCO)[C@@H](O)[C@H]3O)C(N[C@@H]4C[C@H]4C5=CC=C(F)C(F)=C5)=N1

InChI

InChIKey=OEKWJQXRCDYSHL-FNOIDJSQSA-N
InChI=1S/C23H28F2N6O4S/c1-2-7-36-23-27-21(26-15-9-12(15)11-3-4-13(24)14(25)8-11)18-22(28-23)31(30-29-18)16-10-17(35-6-5-32)20(34)19(16)33/h3-4,8,12,15-17,19-20,32-34H,2,5-7,9-10H2,1H3,(H,26,27,28)/t12-,15+,16+,17-,19-,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H28F2N6O4S
Molecular Weight 522.568
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ticagrelor (known trade names Brilinta, Brilique and Possia) is a P2Y12 platelet inhibitor. Brilinta has been approved by the US Food and Drug administration (FDA) in 2011 and is indicated to reduce the rate of cardiovascular death, myocardial infarction, and stroke in patients with acute coronary syndrome (ACS) or a history of myocardial infarction. Brilinta also reduces the rate of stent thrombosis in patients who have been stented for treatment of ACS. Ticagrelor and its major metabolite reversibly interact with the platelet P2Y12 ADP-receptor to prevent signal transduction and platelet activation. Ticagrelor and its active metabolite are approximately equipotent. In vitro metabolism studies demonstrate that ticagrelor and its major active metabolite are weak inhibitors of CYP3A4, potential activators of CYP3A5 and inhibitors of the P-gp transporter. Most common adverse reactions are bleeding 12% and dyspnea 14%.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
BRILINTA
Secondary
BRILINTA

Cmax

ValueDoseCo-administeredAnalytePopulation
1208 ng/mL
270 mg single, oral
TICAGRELOR plasma
Homo sapiens
1208 ng/mL
360 mg single, oral
TICAGRELOR plasma
Homo sapiens
1583 ng/mL
200 mg 2 times / day multiple, oral
TICAGRELOR plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
12379 ng*h/mL
270 mg single, oral
TICAGRELOR plasma
Homo sapiens
12381 ng*h/mL
360 mg single, oral
TICAGRELOR plasma
Homo sapiens
10160 ng × h/mL
200 mg 2 times / day multiple, oral
TICAGRELOR plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
90 mg single, oral
TICAGRELOR plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
90 mg single, oral
TICAGRELOR plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Initiate treatment with 180 mg (two 90 mg tablets) oral loading dose. Continue treatment with 90 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
In human liver microsomes, ticagrelor inhibited midazolam 4-hydroxylation with an IC50 of 8.2 uM. Evaluated in fresh human hepatocytes at concentration up to 20 uM, ticagrelor was not an inducer of CYP1A2 or CYP3A4.
Substance Class Chemical
Record UNII
GLH0314RVC
Record Status Validated (UNII)
Record Version