COLUMBIA, S.C. (AP) — A South Carolina man sent to death row twice for separate murders was put to death Friday by lethal injection in the state’s sixth execution in nine months.

Stephen Stanko, 57, was pronounced dead at 6:34 p.m.

He was executed for shooting a friend and then cleaning out his bank account in Horry County in 2005.

The execution began After a 3 1/2 minute final statement where Stanko apologized to his victims and asked not to be judged by the worst day of his life. Prison officials asked for the first dose of the powerful sedative pentobarbital.

Stanko appeared to be saying words, turned toward the families of the victims and then let out several quick breaths as his lips quivered.

Stanko appeared to stop breathing after a minute. A prison employee asked for a second dose of pentobarbital about 13 minutes later. He was announced dead about 28 minutes after the execution started.

Stanko also was serving a death sentence for killing his live-in girlfriend in her Georgetown County home hours earlier, strangling her as he raped her teenage daughter. Stanko slit the teen’s throat, but she survived.

Stanko was leaning toward dying by South Carolina’s new firing squad, like the past two inmates before him. But after autopsy results from the last inmate killed by that method showed the bullets from the three volunteers nearly missed his heart, Stanko went with lethal injection.

Stanko was the last of four executions scheduled around the country this week. Florida and Alabama each put an inmate to death on Tuesday. On Wednesday, Oklahoma executed a man transferred from federal to state custody to allow his death.

The federal courts rejected Stanko’s last-ditch effort to spare his life as his lawyers argued the state isn’t carrying out lethal injection properly after autopsy results found fluid in the lungs of other inmates killed that way.

Also South Carolina Gov. Henry McMaster refused clemency.in a phone call to prison officials minutes before the execution began.

A governor has not spared a death row inmate’s life in the previous 48 executions since South Carolina reinstated the death penalty about 50 years ago.