LOS ANGELES, California (CNN) -- Anna Nicole Smith's boyfriend and two doctors entered "not guilty" pleas Wednesday to new charges connected to the death of the former Playboy model and reality TV star in 2007.
Howard K. Stern appeared in court on charges connected to the death of Anna Nicole Smith.
Howard K. Stern, Smith's lawyer and companion, appeared in Los Angeles County Superior Court, along with Dr. Khristine Eroshevich and Dr. Sandeep Kapoor to formally hear the charges.
Smith's death in a Hollywood, Florida, hotel on February 8, 2007, was ruled to be from "acute combined drug intoxication," the Broward County, Florida medical examiner said.
The three are charged with an illegal conspiracy to prescribe, administer and dispense controlled substances to an addict. Stern faces 11 felony counts, while the doctors were charged with six each.
They were all charged earlier this year with conspiring to give Smith drugs, but prosecutors revised the counts based on the latest findings from the investigation. The three defendants previously entered "not guilty" pleas to those charges. A preliminary hearing is set for next month in the case.
A series of affidavits used by state investigators to obtain search warrants in their 2½-year probe was unsealed and released Tuesday. They revealed new details, including an account of one witness who told investigators she saw Stern inject Smith with drugs.
A nanny hired to care for Smith's infant daughter, who was born in the Bahamas in September 2006, told investigators she witnessed Stern and Dr. Eroshevich "crush pills, heat them to turn them into liquid and inject Smith," according to an affidavit from a state investigator.
The nanny stated that "after taking pills or being injected Smith would be 'like you were drinking,' often falling in the house, and sleeping for two or more days at a time," California Bureau of Narcotics Enforcement Special Agent Danny Santiago said in a sworn statement.
Doctors gave Smith numerous dangerous drugs over the three years before her death, including while she was pregnant, according to the affidavits.
One investigator described Smith, whose real name was Vickie Lynn Marshall, as a "drug seeker."
She "was given drugs in excessive amounts," according to a medical expert consulted and quoted by a state medical board investigator.
Dr. Jill Klessig also told an investigator that "in addition to the prescribing issues, there appears to have been a personal relationship" between Smith and the two doctors that crossed the boundaries of professionalism.
Investigators found photos of Dr. Eroshevich -- a woman -- and Smith "naked in the bathtub in intimate embraces," according to one sworn statement. Dr. Klessig said "such behavior constitutes unprofessional behavior."
One affidavit references a video clip of Kapoor "kissing and snuggling" with Smith "in a reclined position in a nightclub setting."
Eroshevich traveled to the Bahamas to visit Smith and was with her for four days in Hollywood, Florida, four days before her death, an investigator said in an affidavit.
The doctor personally visited a Burbank, California, pharmacy in September 2006 to get chloral hydrate, a sleep aid, for Smith to use in the Bahamas. It was just four days after Smith gave birth to a daughter in Nassau.
"I wouldn't give her chloral hydrate unless you want your picture on the front page of the National Enquirer," pharmacist Steve Mazlin told Eroshevich, according to the affidavit.
Another pharmacist said that when he refused to fill a prescription for a long list of strong narcotics, he told Dr. Eroshevich the order amounted to "pharmaceutical suicide."
The affidavit from Jon Genens, a senior investigator with the California medical board, detailed dozens of prescriptions written for Smith -- under several aliases -- for a long list of narcotics and sleep aids.
Genens said even during her pregnancy, starting in January 2006, Kapoor prescribed an average of 10 tablets of methadone per day for Smith. He noted that Kapoor lowered the dosage in the last three months of her pregnancy.
The volume of dangerous drugs being ordered by doctors spurred the chief pharmacist at the store where most of the prescriptions were filled to call a drug expert for advice in late 2006, according to a sworn statement by California Department of Justice Special Agent Jennifer Doss.
Dr. Greg Thompson told Doss that he recalled the dosages were "dangerously high."
"Dr. Thompson stated they might work for a drug addict under supervised care, or with a dying cancer patient in a hospital, or 'if you were going to kill someone,' " Doss said. Thompson told Doss he later "admonished Dr. Eroshevich" about the drugs she was requesting for Smith.
"Dr. Thompson stated Dr. Eroshevich was obviously not familiar with a lot of medications she was prescribing for Anna Nicole Smith," Doss said in her affidavit.
The Doss affidavit said the doctor used Smith's boyfriend as a cover to get the prescriptions filled.
"Of the 12 medications found in Anna Nicole Smith's hotel room at the time of her death, seven medications were prescribed in the name of Howard K Stearn (believed to be Howard K Stern) by Dr. Eroshevich," Doss said.
The drugs were apparently personally delivered to Smith in the Bahamas and Florida by her doctor, Doss said.
"It is reasonable to believe that Dr. Eroshevich provided Anna Nicole Smith prescription medications and controlled substances by transporting them from California to Nassau, Bahamas with her on her travels to visit Anna Nicole Smith," Doss said.
CNN's Jack Hannah contributed to this report.