5.04187

P2Y Antagonist II, BPTU

• Synonyme(s) : P2Y Antagonist II, BPTU, Purinergic Receptor P2Y Antagonist II, 1-(2-(2- tert-Butylphenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea, Purinergic Receptor P2Y Antagonist II, 1-(2-(2-tert-Butylphenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea
• Formule empirique (notation de Hill) : C₂₃H₂₂F₃N₃O₃
• Numéro CAS: 870544-59-5
• Poids moléculaire : 445.43
• Numéro MDL: MFCD28386231
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Essai: ≥99% (HPLC)
• Niveau de qualité: 100
• Forme: powder
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; protect from light
• Couleur: white
• Solubilité: DMSO: 100 mg/mL
• Température de stockage: 2-8°C
• Chaîne SMILES: FC(F)(F)Oc1ccc(cc1)NC(=O)Nc2c(nccc2)Oc3c(cccc3)C(C)(C)C
• InChI: 1S/C23H22F3N3O3/c1-22(2,3)17-7-4-5-9-19(17)31-20-18(8-6-14-27-20)29-21(30)28-15-10-12-16(13-11-15)32-23(24,25)26/h4-14H,1-3H3,(H2,28,29,30)
• Clé InChI: AHFLGPTXSIRAQK-UHFFFAOYSA-N

Description

Description générale

A phenoxypyridinyl-phenylurea that acts as a highly selective P2Y₁ antagonist (K_i = 6 nM against 0.5 nM [β-³³P]-2-MeS-ADP in competitive binding assays toward human P2Y₁), while displaying much reduced or no affinity toward other P2Y family G-protein-coupled purinergic receptors (K_i = ≥2.5 µM against 0.5 nM [β-³³P]-2-MeS-ADP binding toward hP2Y₁₄; K_i >15 µM toward human P2Y₂, P2Y₆, P2Y₁₁, and P2Y₁₂). Effectively inhibits 2.5 µM ADP-induced platelet aggregation in vitro (IC₅₀ = 2.1 µM using human platelet rich plasma) and reduces FeCl₂-induced (via 10 min localized artery surface exposure to 50% FeCl₂) carotid artery internal thrombus (blood clot) formation in anesthetized rats in vivo (by 68% 50 min post 10 min FeCl₂ exposure; single 10 mg/kg i.v. 15 min prior to FeCl₂ exposure, followed by continuous i.v. infusion at 10 mg/kg/h) with only 3.3- and 3.1-fold enhanced cuticle and mesenteric bleeding time, respectively. The same antithrombosis efficacy when achieved with the P2Y₁₂ antagonist Clopidogrel (20 mg/kg p.o.) is reported to result in much prolonged cuticle and mesenteric bleeding time (4.1- and 8.2-fold of control level, respectively). Pharmacokinetic studies in rats indicate a moderate oral bioavailability (F = 10%; C_max = 5.83 µM; T_max = 2 h; T_1/2 = 1.43 h; 30 mg/kg delivered with 10% cremophor:10% EtOH:80% H₂O).

Actions biochimiques/physiologiques

Primary Target
P2Y₁

Reversible: yes

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Autres remarques

Zhang, D., et al. 2015. Nature In press.
Chao, H., et al. 2013. J. Med. Chem.56, 1704.

Informations légales

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable