10,11-EDP epoxide

(±)10(11)-EDP ethanolamide is an ω-3 endocannabinoid epoxide and cannabinoid (CB) receptor agonist (EC₅₀s = 0.43 and 22.5 nM for CB₁ and CB₂ receptors, respectively). It is produced though direct epoxygenation of docosahexaenoyl ethanolamide (DHEA; ) by cytochrome P450 (CYP) epoxygenases. 10,11-EDP epoxide (12.5 and 25 μM) reduces the viability of 143B metastatic osteosarcoma cells. It induces apoptosis and inhibits cell migration in a wound-healing assay in 143B, MG63, and HOS osteosarcoma cells. (±)10(11)-EDP ethanolamide also reduces tube formation by human umbilical vein endothelial cells (HUVECs) in a Matrigel™ assay.