SAN ANTONIO >> iHeartMedia Inc. lost $174 million in the second quarter as the radio, billboard and digital giant edged closer to bankruptcy as it struggles under more than $20 billion in debt, the company said Thursday.

The San Antonio-based company’s second-quarter loss narrowed from a loss of $278.9 million during the same three months last year, the company said in releasing its earnings results Thursday. It was the company’s 28th loss over the last 29 quarters.

Revenue dropped to $1.59 billion in the second quarter, from $1.62 billion a year ago, a 1.5 percent decline.

Analysts right now aren’t concerned about profits as its been more than 7 years since the company’s been solidly profitable. They are instead keeping a close watch on iHeartMedia’s cash flow, which is key to its ability to stay afloat.

iHeartMedia, which owns more than 850 radio stations and sponsors popular music festivals across the U.S., reiterated its April 20 warning to investors that it may not survive another year. The company has generated negative cash flow over the last two years, meaning that it’s spending more money on its debt and other expenses than it’s generating.

Cash flow decreased 5.5 percent to $454 million in the second quarter from $482.8 million in the same period last year.

“We will continue to incur net losses and generate negative cash flows from operating activities as a result of our indebtedness and significant related interest expense,” the company said in its earnings release. It repeated its warning in May that if it can’t refinance its debt or find other liquidity, “forecasted cash flows would not be sufficient for us to meet our obligations.”

The company’s cash on hand is dwindling quarter to quarter. It had $845 million in cash on Dec. 31 and $365 million at the end of the first quarter.

As of June 30, its cash on hand dropped to $260.5 million. iHeartMedia warned investors that unless the company can refinance its debt and extend credit facilities that expire at the end of this year, it will likely start missing some of its bond payments beginning early next year.

“That is not headed in the right direction. (Debt costs) are eating away a lot from the cash position,” said Seth Crystall, Debtwire senior credit analyst.

But the revenue and cash flow from radio and billboard advertising should improve during the third and fourth quarters, allowing iHeartMedia to cover its obligations through the end of this year, Crystall said.

iHeartMedia’s has a revolving-credit facility secured by advertising revenue that expires at the end of 2017. But the company is confident that the account can be renewed, said iHeartMedia President, Chief Operating Officer and Chief Financial Officer Rich Bressler.

During a conference call with analysts Thursday, Bressler emphasized that advertising volume has been lower this year than expected. Capital expenditures, including installing new digital billboards, have risen because of higher expectations for advertising, but capital spending will be scaled back, Bressler said.

“Second-quarter revenue came in close to expected. Expenses were a little high. Advertising is weaker than the company thought it would be earlier this year. Management will adjust expenses to address that. Debt is still high. The cash balances are going down. Management will have to address the balance sheet. The negative cash flow, that goes on,” Crystall said.

Bressler told analysts the radio advertising environment is growing tougher because of competition, citing two giant digital companies, Google and Facebook.

“Google and Facebook are doing well,” Crystall acknowledged. “They are taking that from somewhere.”

Total debt at the company stood at $20.38 billion on June 30, up slightly from $20.37 billion on Dec. 31.

Much of iHeartMedia’s debt stems from 2008 when 70 percent of the company, then called Clear Channel Communications, was sold to two Boston-based private equity firms, Bain Capital Partners and Thomas H. Lee Partners. About 30 percent of the company remains publicly traded on the over-the-counter market.

The company, which is in the midst of a $14.6 billion debt exchange offer to lenders and bondholders, Thursday extended the deadline another two weeks to Aug. 18.

Bressler and Coleman didn’t discuss their negotiations with lenders and bondholders.

The company’s main owners, Bain and Lee, are offering lenders and bondholders up to 49 percent in equity of the radio and billboard units if enough of them accept the debt-exchange offer terms, which center on reducing principle amounts on existing bonds and loans and extending maturities by two years.

So far, only 0.6 percent of the $14.6 billion has been exchanged under the current offer, the company said Thursday.

Roughly $317.6 million in bonds and loans come due this year, $324 million in 2018 and $8.4 billion in 2019.

The company could buy itself some time if a little more than half of the loans can be refinanced under the debt exchange offer, said Philip Brendel, a Bloomberg Intelligence credit analyst.

“If more than half of the loans in the debt-exchange offer participate, the company could amend its loan agreement to eliminate the threat of a ‘going concern’ language default, which would alleviate the risk of default up to its January 2019 maturity,” Brendel said.

iHeartMedia’s billboard unit, Clear Channel Outdoor Holdings Inc., reported a $4.78 million second-quarter loss Thursday, narrower than the $69.11 million loss the same quarter a year ago.

Outdoor advertising revenues fell to $687.8 million in the second quarter from $708.1 million a year earlier, a 2.9 percent decline.

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