Updated

Lawyers for a condemned Virginia inmate have filed an emergency motion for a restraining order to stay the execution, which is scheduled for next month.

Court documents show that attorneys for Ricky Gray filed motions for a temporary restraining order and a preliminary injunction Friday. Attorneys are asking the U.S. District Court in Richmond to stay the execution due to the risk that he will suffer a painful death.

Gray was convicted of killing a family of four, including two young girls, in Richmond in 2006. His execution set for Jan. 18.

Earlier this week, Gray's lawyers asked the court to block his execution, in which the state will use drugs from a secret compounding pharmacy.

A spokesman for the Virginia attorney general did not immediately respond to a request for comment.