German company Deutsche Bank has been fined $258m (£167m) by US regulators for working with US-sanctioned countries Syria and Iran.
The bank will pay penalties to the New York State Department of Financial Services and the Federal Reserve.
Employees who worked on the illegal transactions must not work with the bank again, the Federal Reserve said.
The bank also violated various New York state laws and is paying the two agencies separately.
"The firm did not have sufficient policies and procedures to ensure that activities conducted at its offices outside of the United States complied with US sanctions laws," an official from the Federal Reserve said.