Ticagrelor | AZD-6140 | AR-C 126532XX | CAS#274693-27-5

MedKoo Cat#: 300147 | Name: Ticagrelor

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ticagrelor, also known as AZD-6140 and AR-C 126532XX, is a platelet aggregation inhibitor produced by AstraZeneca. The drug was approved in 2011. Ticagrelor is an antagonist of the P2Y12 receptor. Like the thienopyridines prasugrel, clopidogrel and ticlopidine, ticagrelor blocks adenosine diphosphate (ADP) receptors of subtype P2Y12. In contrast to the other antiplatelet drugs, ticagrelor has a binding site different from ADP, making it an allosteric antagonist, and the blockage is reversible. Moreover, the drug does not need hepatic activation, which might work better for patients with genetic variants regarding the enzyme CYP2C19.

Chemical Structure

Ticagrelor

CAS#274693-27-5

Theoretical Analysis

MedKoo Cat#: 300147

Name: Ticagrelor

CAS#: 274693-27-5

Chemical Formula: C23H28F2N6O4S

Exact Mass: 522.1861

Molecular Weight: 522.57

Elemental Analysis: C, 52.86; H, 5.40; F, 7.27; N, 16.08; O, 12.25; S, 6.14

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 450.00	Ready to ship
5g	USD 750.00	Ready to ship
10g	USD 1,250.00	Ready to ship
20g	USD 1,850.00	Ready to ship
50g	USD 3,450.00	Ready to ship

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Related CAS #

No Data

Synonym

AZD-6140; AZD6140; AZD 6140; AR-C 126532XX; AR-C-126532XX; AR-C126532XX; Ticagrelor; brand name: Brilinta; Brilique; Possia

IUPAC/Chemical Name

(1S,2S,3R,5S)-3-[7-[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropylamino]-5-(propylthio)- 3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

InChi Key

OEKWJQXRCDYSHL-FNOIDJSQSA-N

InChi Code

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

SMILES Code

O[C@H]1[C@@H](O)[C@H](N2N=NC3=C(N[C@H]4[C@H](C5=CC=C(F)C(F)=C5)C4)N=C(SCCC)N=C32)C[C@@H]1OCCO

Appearance

White to off-white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#CRB60627

QC Data

View QC data: current batch, Lot#CRB60627

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Ticagrelor (AZD6140) is a reversible P2Y12 receptor antagonist.

In vitro activity:

The most profound effect was through actors of the PERK branch, as CHOP and PERK mRNA levels were significantly increased after treatment with ticagrelor (Figure 6A,B). The ER chaperone BiP—which can activate all three ER stress branches—showed a non-significant increase after ticagrelor treatment (Figure 6A,D) and treatment with ticagrelor did not affect the levels of ATF6 (Figure 6A). To evaluate if there was a dose-dependent effect on the expression of ER stress markers, THP1-differentiated macrophages were exposed to 0 µM, 0.5 µM and 1 µM ticagrelor. Notably, 1 µM ticagrelor lead to a 20-fold increase in the expression of CHOP (Figure 6B), which could have contributed to the toxicity of ticagrelor at higher concentrations, as CHOP is an important mediator in ER stress-induced apoptosis. Reference: Int J Mol Sci. 2020 Nov; 21(21): 8177. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7672568/

In vivo activity:

The data support the notion that ticagrelor's antimetastatic effect is due to inhibition of P2Y12 activation on platelets. When a monoclonal antibody against GPIIbIIIa was combined with platelets from ticagrelor-treated mice, this study observed no additional reduction in platelet–tumor cell binding below that observed with ticagrelor-treated platelets or antibody treatment alone, suggesting that ticagrelor prevents platelet–tumor cell interactions by inhibiting GPIIbIIIa activity. This supports the earlier observation that tumor cell–platelet interactions are mediated through engagement of αVβ3 integrin on B16-F10 cells with GPIIbIIIa on platelets. The observation that direct treatment of endothelial cells with ticagrelor had no effect on tumor cell–endothelial interactions is likely due to endothelial ADP signaling being mediated primarily through P2Y2. Findings support the notion that ticagrelor may act indirectly on endothelium by disrupting platelet ADP and ATP secretion necessary for P2Y2 activation and hence transendothelial tumor cell migration. Reference: Int J Cancer. 2015 Jan 1;136(1):234-40. https://onlinelibrary.wiley.com/doi/full/10.1002/ijc.28947

	Solvent	mg/mL	mM
Solubility
	DMSO	40.8	77.99
	DMF	25.0	47.84
	DMF:PBS (pH 7.2) (1:5)	0.2	0.29
	Ethanol	15.0	28.70

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 522.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Pavlović N, Kopsida M, Gerwins P, Heindryckx F. Inhibiting P2Y12 in Macrophages Induces Endoplasmic Reticulum Stress and Promotes an Anti-Tumoral Phenotype. Int J Mol Sci. 2020 Oct 31;21(21):8177. doi: 10.3390/ijms21218177. PMID: 33142937; PMCID: PMC7672568. 2. Mitsios A, Chrysanthopoulou A, Arampatzioglou A, Angelidou I, Vidali V, Ritis K, Skendros P, Stakos D. Ticagrelor Exerts Immune-Modulatory Effect by Attenuating Neutrophil Extracellular Traps. Int J Mol Sci. 2020 May 21;21(10):3625. doi: 10.3390/ijms21103625. PMID: 32455533; PMCID: PMC7279443. 3. Lu W, Gómez NM, Lim JC, Guha S, O'Brien-Jenkins A, Coffey EE, Campagno KE, McCaughey SA, Laties AM, Carlsson LG, Mitchell CH. The P2Y12 Receptor Antagonist Ticagrelor Reduces Lysosomal pH and Autofluorescence in Retinal Pigmented Epithelial Cells From the ABCA4-/- Mouse Model of Retinal Degeneration. Front Pharmacol. 2018 Apr 19;9:242. doi: 10.3389/fphar.2018.00242. PMID: 29725296; PMCID: PMC5917064. 4. Gebremeskel S, LeVatte T, Liwski RS, Johnston B, Bezuhly M. The reversible P2Y12 inhibitor ticagrelor inhibits metastasis and improves survival in mouse models of cancer. Int J Cancer. 2015 Jan 1;136(1):234-40. doi: 10.1002/ijc.28947. Epub 2014 May 14. PMID: 24798403.

In vitro protocol:

In vivo protocol:

1. Lu W, Gómez NM, Lim JC, Guha S, O'Brien-Jenkins A, Coffey EE, Campagno KE, McCaughey SA, Laties AM, Carlsson LG, Mitchell CH. The P2Y12 Receptor Antagonist Ticagrelor Reduces Lysosomal pH and Autofluorescence in Retinal Pigmented Epithelial Cells From the ABCA4-/- Mouse Model of Retinal Degeneration. Front Pharmacol. 2018 Apr 19;9:242. doi: 10.3389/fphar.2018.00242. PMID: 29725296; PMCID: PMC5917064. 2. Gebremeskel S, LeVatte T, Liwski RS, Johnston B, Bezuhly M. The reversible P2Y12 inhibitor ticagrelor inhibits metastasis and improves survival in mouse models of cancer. Int J Cancer. 2015 Jan 1;136(1):234-40. doi: 10.1002/ijc.28947. Epub 2014 May 14. PMID: 24798403.

1: Nylander S, Schulz R. Effects of P2Y12 receptor antagonists beyond platelet inhibition - comparison of ticagrelor with thienopyridines. Br J Pharmacol. 2016 Apr;173(7):1163-78. doi: 10.1111/bph.13429. Epub 2016 Feb 24. Review. PubMed PMID: 26758983. 2: Guimarães PO, Tricoci P. Ticagrelor, prasugrel, or clopidogrel in ST-segment elevation myocardial infarction: which one to choose? Expert Opin Pharmacother. 2015;16(13):1983-95. doi: 10.1517/14656566.2015.1074180. Epub 2015 Jul 29. Review. PubMed PMID: 26224244. 3: Bavishi C, Panwar S, Messerli FH, Bangalore S. Meta-Analysis of Comparison of the Newer Oral P2Y12 Inhibitors (Prasugrel or Ticagrelor) to Clopidogrel in Patients With Non-ST-Elevation Acute Coronary Syndrome. Am J Cardiol. 2015 Sep 1;116(5):809-17. doi: 10.1016/j.amjcard.2015.05.058. Epub 2015 Jun 4. Review. PubMed PMID: 26119655. 4: Harding SA, Van Gaal WJ, Schrale R, Gunasekara A, Amerena J, Mussap CJ, Aylward PE. Practical experience with ticagrelor: an Australian and New Zealand perspective. Curr Med Res Opin. 2015 Aug;31(8):1469-77. doi: 10.1185/03007995.2015.1058247. Epub 2015 Jun 30. Review. PubMed PMID: 26086451. 5: Teng R. Ticagrelor: Pharmacokinetic, Pharmacodynamic and Pharmacogenetic Profile: An Update. Clin Pharmacokinet. 2015 Nov;54(11):1125-38. doi: 10.1007/s40262-015-0290-2. Review. PubMed PMID: 26063049; PubMed Central PMCID: PMC4621714. 6: Lemesle G, Schurtz G, Bauters C, Hamon M. High on-treatment platelet reactivity with ticagrelor versus prasugrel: a systematic review and meta-analysis. J Thromb Haemost. 2015 Jun;13(6):931-42. doi: 10.1111/jth.12907. Epub 2015 Apr 21. Review. PubMed PMID: 25809392. 7: Dhillon S. Ticagrelor: a review of its use in adults with acute coronary syndromes. Am J Cardiovasc Drugs. 2015 Feb;15(1):51-68. doi: 10.1007/s40256-015-0108-5. Review. PubMed PMID: 25672642. 8: Chong AY, So DY. Ticagrelor for the treatment of peripheral arterial disease. Expert Opin Investig Drugs. 2014 Dec;23(12):1737-43. doi: 10.1517/13543784.2014.974803. Epub 2014 Nov 6. Review. PubMed PMID: 25376000. 9: Parodi G, Storey RF. Dyspnoea management in acute coronary syndrome patients treated with ticagrelor. Eur Heart J Acute Cardiovasc Care. 2015 Dec;4(6):555-60. doi: 10.1177/2048872614554108. Epub 2014 Sep 29. Review. PubMed PMID: 25267878; PubMed Central PMCID: PMC4657388. 10: Alexopoulos D, Xanthopoulou I, Storey RF, Bliden KP, Tantry US, Angiolillo DJ, Gurbel PA. Platelet reactivity during ticagrelor maintenance therapy: a patient-level data meta-analysis. Am Heart J. 2014 Oct;168(4):530-6. doi: 10.1016/j.ahj.2014.06.026. Epub 2014 Jul 11. Review. PubMed PMID: 25262263. 11: Rognoni A, Cavallino C, Lupi A, Secco GG, Veia A, Bacchini S, Rosso R, Brunelleschi S, Rametta F, Bongo AS. Ticagrelor: a novel drug for an old problem. Recent Pat Cardiovasc Drug Discov. 2014;9(1):51-7. Review. PubMed PMID: 25174338. 12: Dobesh PP, Oestreich JH. Ticagrelor: pharmacokinetics, pharmacodynamics, clinical efficacy, and safety. Pharmacotherapy. 2014 Oct;34(10):1077-90. doi: 10.1002/phar.1477. Epub 2014 Aug 28. Review. PubMed PMID: 25164528; PubMed Central PMCID: PMC4282310. 13: Cattaneo M, Schulz R, Nylander S. Adenosine-mediated effects of ticagrelor: evidence and potential clinical relevance. J Am Coll Cardiol. 2014 Jun 17;63(23):2503-9. doi: 10.1016/j.jacc.2014.03.031. Epub 2014 Apr 23. Review. PubMed PMID: 24768873. 14: Bonaca MP, Bhatt DL, Braunwald E, Cohen M, Steg PG, Storey RF, Held P, Jensen EC, Sabatine MS. Design and rationale for the Prevention of Cardiovascular Events in Patients With Prior Heart Attack Using Ticagrelor Compared to Placebo on a Background of Aspirin-Thrombolysis in Myocardial Infarction 54 (PEGASUS-TIMI 54) trial. Am Heart J. 2014 Apr;167(4):437-444.e5. doi: 10.1016/j.ahj.2013.12.020. Epub 2014 Jan 6. Review. PubMed PMID: 24655690. 15: Bonhomme F, Fontana P, Reny JL. How to manage prasugrel and ticagrelor in daily practice. Eur J Intern Med. 2014 Mar;25(3):213-20. doi: 10.1016/j.ejim.2014.01.016. Epub 2014 Feb 12. Review. PubMed PMID: 24529662. 16: Morici N, Colombo P, Mafrici A, Oreglia JA, Klugmann S, Savonitto S. Prasugrel and ticagrelor: is there a winner? J Cardiovasc Med (Hagerstown). 2014 Jan;15(1):8-18. doi: 10.2459/JCM.0b013e328364561b. Review. PubMed PMID: 24500235. 17: Tsang K, Hartmark-Hill JR. Ticagrelor (Brilinta) for secondary prevention of thrombotic events following acute coronary syndrome. Am Fam Physician. 2013 Dec 15;88(12):821-2. Review. PubMed PMID: 24364545. 18: Serebruany VL, Sibbing D, DiNicolantonio JJ. Dyspnea and reversibility of antiplatelet agents: ticagrelor, elinogrel, cangrelor, and beyond. Cardiology. 2014;127(1):20-4. doi: 10.1159/000354876. Epub 2013 Oct 26. Review. PubMed PMID: 24192670. 19: Bansilal S, Bonaca MP, Sabatine MS. Ticagrelor for acute coronary syndromes. Expert Rev Cardiovasc Ther. 2013 Nov;11(11):1473-84. doi: 10.1586/14779072.2013.839205. Epub 2013 Oct 23. Review. PubMed PMID: 24147518. 20: Norgard NB, Dinicolantonio JJ. Clopidogrel, prasugrel, or ticagrelor? a practical guide to use of antiplatelet agents in patients with acute coronary syndromes. Postgrad Med. 2013 Jul;125(4):91-102. doi: 10.3810/pgm.2013.07.2682. Review. PubMed PMID: 23933898.