Ifetroban sodium

• CAT Number: I029204
• CAS Number: 156715-37-6
• Molecular Formula: C25H31N2NaO5
• Molecular Weight: 462.51
• Purity: ≥95%
• Synonyms: sodium;3-[2-[[(1S,2R,3S,4R)-3-[4-(pentylcarbamoyl)-1,3-oxazol-2-yl]-7-oxabicyclo[2.2.1]heptan-2-yl]methyl]phenyl]propanoate
• InChI: InChI=1S/C25H32N2O5.Na/c1-2-3-6-13-26-24(30)19-15-31-25(27-19)23-18(20-10-11-21(23)32-20)14-17-8-5-4-7-16(17)9-12-22(28)29;/h4-5,7-8,15,18,20-21,23H,2-3,6,9-14H2,1H3,(H,26,30)(H,28,29);/q;+1/p-1/t18-,20-,21+,23-;/m0./s1
• InChIKey: WOHSQDNIXPEQAE-QBKVZTCDSA-M
• SMILES: CCCCCNC(=O)C1=COC(=N1)C2C3CCC(C2CC4=CC=CC=C4CCC(=O)[O-])O3.[Na+]

Ifetroban (BMS-180291) sodium is an orally active antagonist of thromboxane A2 (TXA2) or prostaglandin H2 (PGH2) receptor. Ifetroban sodium shows antiplatelet activity, and inhibits tumor cell migration without affecting cell proliferation. Ifetroban sodium can be used for myocardial ischemia, hypertension, stroke, thrombosis, cardiomyopathy research[1][2][3][4].
Ifetroban sodium (CPI211) (100 nM; 48 h) results Tpr inhibition and potently blocks spontaneous metastasis from primary tumors, without affecting tumor cell proliferation, motility, or tumor growth in 4T1 cells (mouse mammary cancer)[2].
Ifetroban sodium (100 nM; 6 h) strongly inhibits PKC substrate phosphorylation, and blocks agonist (U46619, HY-108566)-induced TPr diminution in human umbilical vein endothelial cells (HUVECs)[2].
Ifetroban sodium (50 mg/kg/d; p.o.; 2 d prior to, through 28 d after tumor injection) decreases hematogenous metastasis of multiple cancer types without in mice model[2].
Ifetroban sodium (50 mg/kg/d; p.o.; 12 d) does not affect primary tumor growth but decreases tumor vessels in mice with 4T1 (mouse mammary cancer)[2].
Ifetroban sodium (BMS 180,291; 1 and 3 mg/kg, p.o.) inhibits aggregation and antagonizes TP-receptor in monekys. Ifetroban sodium (3 mg/kg, i.v.) causes only marginal and transient hemodynamic effects in anesthetized African green monkeys[3].

Reference

[1]. Johnson RA, et al. Effect of ifetroban, a thromboxane A2 receptor antagonist, in stroke-prone spontaneously hypertensive rats. Clin Exp Hypertens. 1996 Feb;18(2):171-88.
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[2]. Werfel TA, et al. Repurposing of a Thromboxane Receptor Inhibitor Based on a Novel Role in Metastasis Identified by Phenome-Wide Association Study. Mol Cancer Ther. 2020 Dec;19(12):2454-2464. 
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[3]. Schumacher WA, et al. Antiplatelet activity of the long-acting thromboxane receptor antagonist BMS 180,291 in monkeys. Prostaglandins. 1992 Nov;44(5):389-97.
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[4]. Rosenfeld L, et al. Ifetroban sodium: an effective TxA2/PGH2 receptor antagonist. Cardiovasc Drug Rev. 2001 Summer;19(2):97-115. 
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