The present invention relates to lipid compounds, which can be used alone or in combination with other lipid components such as neutral lipids, charged lipids, steroids and / or their analogs, and / or lipid-conjugated polymers to form lipid nanoparticles for delivering therapeutic and / or prophylactic agents. In some instances, the lipid nanoparticles are used to deliver nucleic acids, such as
messenger RNA and / or
antisense RNA. Methods of using such lipid nanoparticles to treat and / or prevent various diseases are also provided. In one embodiment, a compound having the structure of formula (I) is provided: or a salt or an isomer or an N-
oxide thereof, wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Pharmaceutical compositions comprising one or more of the compounds of the foregoing
structural formula (I) and a therapeutic and / or prophylactic agent are also provided. In some embodiments, the pharmaceutical composition further comprises one or more components selected from neutral lipids, charged lipids, steroids and lipid-conjugated polymers. Such compositions are useful for forming lipid nanoparticles for delivering therapeutic and / or prophylactic agents. In other embodiments, the present invention provides a method of administering a therapeutic and / or prophylactic agent to a subject in need thereof, the method comprising preparing a pharmaceutical combination of a lipid
nanoparticle comprising a compound of
structural formula (I) and a therapeutic and / or prophylactic agent, and delivering the composition to the subject.