A man and three teenagers have been charged with drugging a woman at a pizza shop in Sydney's south before taking it in turns to rape her, police say.
The alleged attack on the 18-year-old woman occurred at the shop on Forest Road in Lugarno on October 15, after she went there with a 17-year-old male friend, one of those now charged over her aggravated sexual assault.
A NSW Police spokeswoman said the pair were at the pizza shop about 8pm that Saturday when they met another 17-year-old boy, a 15-year-old boy and a 38-year-old man.
Police will allege in court that the three males who met them were known to the 17-year-old boy who was originally with the alleged victim.
During the night, a drug was allegedly put in the woman's wine glass.
"Police will allege the woman was given an unknown substance and, while under the influence, she was sexually assaulted a number of times by the boys and man," the spokeswoman said.
Police will allege in court that the sexual assault occurred at the rear of the pizza shop.
The males are then accused of driving the woman to nearby Riverwood several hours later and dropping her in the centre of the suburb.
A passerby called triple zero after finding the woman disoriented on the road.
NSW Ambulance paramedics treated the woman at the scene, before taking her to Liverpool Hospital, where staff called police.
Officers from the St George Local Area Command launched an investigation and, on Thursday, arrested the four males.
They were taken to Liverpool police station and were each charged with aggravated sexual assault in company, and refused bail by police.
The man is due to appear in Liverpool Local Court and the teenagers at a children's court on Friday.