Shares of Zynga Inc. (Nasdaq: ZNGA) sank to a new low Friday following the social game developer’s announcement of a gloomy third-quarter outlook. Prices dropped as low as $2.21 in Fridaytrades, more than 20 percent. The San Francisco company had already lost more than half of its market value since its initial public offering last December.

At the close,, Zynga was at $2.48 down 34, bringing the loss to 74 percent.

Since late July, when a weak second quarter earnings report first sent Zynga’s stock plummeting, the company’s share prices have dropped more than 70 percent from their opening price of $10 per share and remained stubbornly below $3 despite fleeting moments of recovery. As recently as March, shares in what remains the most popular Facebook Inc. (Nasdaq: FB) social network app developer by a wide margin were trading for as much as $15.

Share prices entered their latest free-fall in after-hours trading Thursday after the company released its preliminary third-quarter earnings report. In the statement, Zynga said it expects to report a net loss somewhere between $90 million and $105 million. For the third quarter, the company expects to report revenue in the range of $300 million to $305 million. Bookings, meanwhile, are expected in the range of $250 million to $255 million – a steep drop from the $302 million Zynga reported in the second quarter.

Writing on the company’s blog following the announcement, Zynga CEO and co-founder Mark Pincus said “the challenges we faced in our web business in Q2 continued in Q3 and while many of our games achieved plan, we still experienced overall weakness in the ‘invest and express’ category.”

As a result, the company lowered its full-year bookings forecast to a range of $1.085 billion to $1.1 billion, compared to its originally forecast of $1.15 billion to $1.23 billion. Citing delays in launching some of its planned new titles, the company said the full-year outlook was lowered to reflect “reduced expectations” for “certain web games,” including the recently launched Facebook game “The Ville” -- a game that is now at the center of a tenuous legal battle with Electronic Arts Inc. (Nasdaq: EA) after EA accused Zynga of infringing on the copyright for its Facebook game “The Sims Social.”

Zynga was careful to specify that the diminished expectations were the results of “certain web games,” however. Reiterating the strategy they first announced after their second quarter earnings report, Pincus said that his company will refocus on mobile gaming and casino games in particular -- a strategy its already acted on by hiring an veteran online gambling executive and contributing to gambling lobbying efforts throughout the United States.

Despite the promise of increasing monetization of its mobile audience, analysts are beginning to doubt Zynga’s ability to recover from its recent tumble at all. Ben Schacter, an analyst at Macquaerie Securities, said to the game industry site Gamasutra "we don't see a floor on the horizon. Our concern has been and remains that while Zynga executed against its first mover advantage on the Facebook platform, off of the platform they are just one of many."

In other words, Zynga lacks the natural advantage it has on the Facebook platform -- the company leads its closest competitor, Microsoft Inc. (Nasdaq: MSFT), by more than 300 million monthly active users on the social media site, according to AppData -- when it comes to any emerging market like mobile. And any number of competitors have already swooped into that space after noticing the rapid and seemingly unstoppable ascent of Zynga itself in just five years.

Pincus went on to say that his company will undergo some “targeted cost reductions,” but gave no specific details. Having already lost 12 C-level executives in less than two months following its second quarter earnings report, however, the statement leaves open the possibility of further cuts to underperforming sections, such as Facebook titles that have failed to attract significant user retention. He also added that Zynga will be “focusing our new game pipeline to reflect our strategic priorities,” but nevertheless conceded that several new games “are at risk of launching later than expected.”

Zynga also noted in its Thursday statement third-quarter results will include a write-down between $85 million and $95 million for the acquisition of OMGPOP, the mobile game studio Zynga acquired in March for about $180 million. The deal was largely motivated by the massive popularity OMGPOP’s mobile game “Draw Something” was enjoying at the time, a popularity that fell sharply less than two months after the acquisition.

“While we’re encouraged by our strong starting position on mobile, developing this new growth market to the scale of our web business will take time,” Pincus wrote.

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