Israeli pharmaceutical giant Teva is among a number of companies fined by the European Commission for breaches of competition regulations.
The EU on Wednesday hit French drugs giant Servier with a huge 331 million euro fine for colluding to delay a cheaper generic version of perindopril, a popular blood pressure treatment.
In a statement, the European Commission said total fines in the case amounted to 427.7 million euros ($582 million), with Israeli generic giant Teva and four other companies also subject to penalties.
Servier is accused of trying to delay the introduction of a generic version of perindopril, a cardio-vascular medicine. The allegation is the result of a broad EU probe into the pharmaceutical industry launched in 2008.
"Servier had a strategy to systematically buy out any competitive threats to make sure that they stayed out of the market," said EU Competition Commissioner Joaquin Almunia.
"Such behaviour is clearly anti-competitive and abusive," he added.
Generic products are far cheaper than brand medicines - on average generics cost 40 percent less two years after they enter the market - and are a huge savings to patients and health care providers while remaining just as effective.
But in so-called pay-for-delay deals, drug makers can pay generic rivals to thwart the introduction of cheaper versions of blockbuster drugs for an agreed time.
The generic companies fined in the Servier case are Teva, Indian companies Niche/Unichem and Lupin, US company Mylan and Slovenia's Krka.
The fine inflicted on Servier is close to the maximum possible of up to 10 percent of the group's total annual sales. In 2013, Servier posted sales of 4.2 billion euros, with a net profit of 325 millions euros.
A year ago, Danish drugmaker Lundbeck was fined 93.8 million euros by the Commission for striking a 2002 agreement to delay the generic version of its popular anti-depressant, citalopram.
Arutz Sheva Staff contributed to this report.