A 23-year-old Makaha man with a history of drug-related charges was expected to be charged Friday with second-degree murder in the shooting death of his one-time friend, 26-year-old Christopher K. Medeiros, himself convicted of five felonies.

Chad Duran allegedly shot Medeiros in the head Wednesday night at Medeiros’ Makaha apartment on Lahaina Street. A neighbor brought Medeiros to the Wai­anae Coast Comprehensive Health Center. Paramedics picked him up and transported him in critical condition to the Queen’s Medical Center, where he died Thursday.

Duran, who lives three streets away from Medeiros on Noho­lio Road, was found and arrested shortly after the shooting on suspicion of attempted murder.

A neighbor of Medeiros said about 10 deputy sheriffs and what appeared to be plainclothes police officers wearing bulletproof vests arrived Friday and seized his redHonda car, but did not see what else occurred.

Police and Department of Public Safety spokes­women could not confirm that, saying the investigation into the shooting is ongoing.

Neighbors say at one time the two men were friends.

Duran had pleaded guilty in 2010 to charges of drug promotion and use of drug paraphernalia, and the court granted him a deferred acceptance of his guilty plea, which would have allowed him to remain free and keep the convictions off his record if he stayed out of trouble.

Instead he was jailed multiple times for probation violation and then ordered Aug. 16 to serve a 15-day intermittent sentence at Oahu Community Correctional Center, turning himself in on weekends beginning Aug. 17. He was expected to complete his sentence Sunday, Department of Public Safety spokes­woman Toni Schwartz said.

Duran also had three temporary restraining orders filed against him by different individuals.

Medeiros had a history of violent crimes:

» In April 2005 he threatened a man with a beer bottle and demanded the keys to his car. He was charged with robbery.

» In October 2005 he punched a man in the face at a Makaha intersection while 15 to 20 people looked on. According to witnesses, the man dropped to the ground and was attacked by several males until he was unconscious, police said in court documents.

» Also in October 2005, Medeiros pulled a woman out of a pickup truck at the Makaha 7-Eleven and punched the driver in the face and fractured his shoulder.

In a plea deal for all three cases in 2007, Medeiros pleaded to the lesser crime of theft in the robbery case and to two counts of second-degree assault, criminal property damage and unauthorized entry into a motor vehicle. He completed a five-year sentence for all crimes on July 31, 2011.