Martin Shkreli, the former pharmaceutical executive best known for unapologetically raising the price of an old drug, must pay $64.6 million and will be barred for life from the drug industry for violating antitrust law in connection with that medicine, a federal court ordered on Friday.Mr. Shkreli is serving a seven-year prison sentence for defrauding investors related to his work running two hedge funds. That conviction is unrelated to the drug pricing saga that elevated him to notoriety. He is expected to be released later this year.In 2015, Mr. Shkreli — then a pharmaceutical entrepreneur in his early 30s not well known outside of his industry — acquired a decades-old drug known as Daraprim, which is used to treat a life-threatening parasitic infection, and raised its price to $750 a tablet, up from $13.50. The incident alarmed politicians and the public, who were already worried about rising drug prices and the role that pharmaceutical companies can play in making medicines unaffordable.Most pharmaceutical executives raise drug prices more quietly and gradually, and with reassurances about ensuring patient access, but Mr. Shkreli seemed unrepentant. He became known as “pharma bro” for his brash attitude when faced with criticism from lawmakers and others over the drug price increase.On Friday, Judge Denise L. Cote of the U.S. District Court for the Southern District of New York ruled that Mr. Shkreli tried to maintain a monopoly over Daraprim through anticompetitive tactics. The lawsuit had been brought by the Federal Trade Commission and the attorneys general of seven states, including New York.The judge found that Mr. Shkreli violated state and federal antitrust laws and that his former company, now known as Vyera Pharmaceuticals, brought in $64.6 million in excess profits from its sales of Daraprim from that conduct.The court found that under Mr. Shkreli’s control, Vyera changed the way the drug was distributed and impeded competition in the generic market. As a result, consumers were harmed by higher prices and fewer options for the drug, “forcing many patients and physicians to make difficult and risky decisions for the treatment of life-threatening diseases,” the New York attorney general’s office said in a news release.Lawyers for Mr. Shkreli did not immediately return a request for comment on Friday afternoon.