NEW YORK (REUTERS) - FriendFinder Networks, which publishes the adult magazine Penthouse, filed for Chapter 11 bankruptcy on Tuesday, a court filing showed.

The holding company, which also houses Internet sites such as adultfriendfinder.com, listed out estimated liabilities of US$500 million (S$632 million) to US$1 billion and assets of US$1 million to US$10 million, a court filing showed.

FriendFinder has not turned in a net profit at least since 2008, Thomson Reuters data shows. Total revenue for the four consecutive fiscal quarters ended June 30 this year was US$293.7 million, a filing showed.

"Despite continuing member interest and high volume traffic, the debtors did not make certain payments to the holders of existing first lien notes and cash pay second lien notes which constituted a default under their respective indentures," FriendFinder said in the filing.

FriendFinder said it agreed with certain holders of its senior debt to restructure its balance sheet and has commenced Chapter 11 proceedings to implement its recapitalisation plan.

In 2010, the owner of Penthouse magazine offered to buy rival Playboy Enterprises for US$210 million. The deal later fell through.