iHeartMedia Inc., the biggest operator of radio stations in the U.S. and headed by Bob Pittman of MTV fame, plans to include language in its next quarterly report warning investors that it may not survive another year.

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The company IHRT, -1.83% , which owns iHeartRadio and billboard advertising company Clear Channel Outdoor Holdings CCO, -8.95% , said it continues to expect cash flow to be negative and is uncertain as to whether it will be able to refinance or extend the maturities of some of its borrowings, according to a regulatory filing.

The company has almost $350 million of debt coming due this year, part of a massive $20 billion debt load it took on as part of a $24 billion leveraged buyout of then Clear Channel Communications Inc. by private-equity firms Bain Capital and Thomas H. Lee Partners in 2008. It has another $8.3 billion of debt coming due in 2019.

“Management anticipates that our financial statements to be issued for the three months ended March 31, 2017, will include disclosure indicating there will be substantial doubt as to our ability to continue as a going concern for a period of 12 months following the date the first quarter 2017 financial statements are issued,” the company said in its filing with the Securities and Exchange Commission.

iHeart’s most active bonds, the 9.00% notes that mature in March of 2021, traded down 2 points to 75 cents on the dollar on Friday, according to MarketAxess. Its 6.875% notes due in June of 2018 were trading at 69 cents on the dollar.

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Moody’s Investors Service said an exchange offer in March, in which iHeart swapped $476 million of senior unsecured notes due 2018 for senior secured priority guarantee notes due 2021, was a continuation of iHeart’s distressed exchange.

As for its stock, shares on Friday fell 3%.

The rating agency had revised the outlook on iHeart’s ratings to negative from stable in December, suggesting it might further downgrade its already deep into junk Caa2 rating in the medium term. Moody’s said at the time it expected iHeart would be forced into a debt restructuring in the next year.

Chairman and CEO of iHeart Media, Inc. Bob Pittman Getty Images

The company attempted in April to persuade its creditors to accept a series of exchange offers that would allow it to refinance more than $14 billion of term loans and other debt, offering new debt, equity and ownership in Clear Channel Outdoor Holdings. After its lenders failed to take up that offer, the company extended the deadline to late April.

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Some experts said bankruptcy is now almost inevitable.

“I think it will go into Chapter 11 and what will happen is what has happened in most of these LBO cases,” said Chuck Tatelbaum, international bankruptcy expert and senior attorney at the Tripp Scott law firm. “The lender will take back the company as part of a Chapter 11 plan, the other creditors will get nothing and the shareholders will be wiped out.”

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iHeart, which began life as a single radio station in San Antonio in the early 1970s, today operates more than 850 radio stations across the U.S. But the radio sector has struggled with competition from the likes of streaming services Pandora US:P and Spotify. That has pressured ad sales, which were already on a downward track as ad dollars flock to companies like Alphabet Inc.’s Google GOOGL, -2.41% GOOG, -2.37% and Facebook Inc. FB, -0.89% that allow advertisers to target specific markets.

The company’s efforts to increase revenue and cash flow have largely failed. Revenue fell 2.4% in the first quarter to $1.33 billion, while expenses rose 3%, according to the SEC filing. Operating income fell 73% to $114 million. As of March 1, the company had $365 million of cash on its balance sheet, including $220.6 million of cash held by Clear Channel Outdoor.

Pittman, who is widely regarded as a marketing genius, took over as CEO in 2011, and immediately embarked on a series of moves aimed at positioning iHeart as a modern tech company with a bright future.

In one instance, he redesigned the company’s New York headquarters into a “Kubrickian spaceship,” as Variety magazine described it, complete with laser displays, modular fiberglass pods and a tunnel with video images projected into streams of mist.

Pittman brought in a new management team and embarked on a campaign of promotional events, including the iHeart concert series, the iHeart Radio Music Awards and lavish parties at the annual ad-industry event, Cannes Lions International Festival of Creativity.

iHeart posted a net loss of $240 million in 2016, after a net loss of $737 million in the year-earlier period.

”The bottom line is you have to have a profit and you have to have sufficient cash flow to function as a company,” said Tatelbaum.

iHeart shares closed down 4.8%. The S&P 500 SPX, -1.11% ended down 0.3%.

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