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SML0331

Sigma-Aldrich

Prasugrel

≥98% (HPLC)

Synonym(s):

5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate, CS 747, CS-747, Effient, Efient, LY640315

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About This Item

Empirical Formula (Hill Notation):
C20H20FNO3S
CAS Number:
150322-43-3
Molecular Weight:
373.44
MDL number:
MFCD09954140
UNSPSC Code:
12352200
PubChem Substance ID:
329825336
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >5 mg/mL (warmed at 60 °C)

storage temp.

2-8°C

SMILES string

CC(=O)Oc1cc2CN(CCc2s1)C(C(=O)C3CC3)c4ccccc4F

InChI

1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3

InChI key

DTGLZDAWLRGWQN-UHFFFAOYSA-N

Gene Information

human ... P2RY12(64805)

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Biochem/physiol Actions

Prasugrel is a platelet inhibitor that reduces the aggregation of platelets by irreversible binding to P2Y12 receptors. Prasugrel interacts in an irreversible manner with the residues Cys97 and Cys175 of the human P2Y12-receptor.
Prasugrel is a thienopyridine prodrug and is considered to be more potent than clopidogrel. It shows a faster generation and also reduces thrombotic events. Prasugrel is less dependent on the CYP (cytochrome P450) enzymes for its conversion to active metabolite.

Features and Benefits

This compound is featured on the P2 Receptors: P2Y G-Protein Family page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yochai Birnbaum et al.
Cardiovascular drugs and therapy, 30(6), 539-550 (2016-11-11)
Ticagrelor inhibits the equilibrative-nucleoside-transporter-1 and thereby, adenosine cell re-uptake. Ticagrelor limits infarct size (IS) in non-diabetic rats and the effect is adenosine-dependent. Statins, via ecto-5'-nucleotidase activation, also increase adenosine levels and limit IS. Ticagrelor and rosuvastatin have additive effects on
Oxford Textbook of Interventional Cardiology, 383-383 (2010)
Platelets, 1125-1125 (2013)
Cynthia Larmore et al.
Catheterization and cardiovascular interventions : official journal of the Society for Cardiac Angiography & Interventions, 88(4), 535-544 (2016-10-21)
The 30-day clinical outcomes with prasugrel or ticagrelor were compared using a US payer database in patients with acute coronary syndrome (ACS) undergoing percutaneous coronary intervention (PCI). Prasugrel and ticagrelor demonstrated superior efficacy with increased non-coronary artery bypass graft major
Martina Rothenbühler et al.
European heart journal, 40(15), 1226-1232 (2019-01-29)
In the Minimizing Adverse Haemorrhagic Events by TRansradial Access Site and Systemic Implementation of angioX (MATRIX) trial, adults with acute coronary syndrome undergoing coronary intervention who were allocated to radial access had a lower risk of bleeding, acute kidney injury
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Articles

P2 Receptors: P2Y G-Protein Family Overview

Surface receptors for extracellular nucleotides are called P2 receptors. Learn more about P2Y G protein-coupled receptors, GPCRs, and ionotropic P2 receptors (P2X ligand-gated ion channels, LGICs).

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