WASHINGTON (AP) — The Trump administration has frozen all Venezuelan government assets in a dramatic escalation of tensions with Nicolás Maduro.

The ban places Maduro’s socialist administration alongside a short list of adversaries from Cuba, North Korea, Syria and Iran that have been targeted by such aggressive U.S. actions.

The ban blocks American companies and individuals from doing business with Maduro’s government and its top supporters. It came Monday night as an executive order from President Donald Trump and takes effect immediately.

Trump’s order spares Venezuela’s still sizable private sector. Yet it represents the most sweeping U.S. action to remove Maduro since the Trump administration recognized opposition leader Juan Guaidó as Venezuela’s rightful leader in January.

The order also exposes foreign entities doing business with the Maduro government to U.S. retaliation.