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If it was purchased through iBooks and won't open with the Calibre reader (or other software besides iBooks) then it likely has Apple's "Fairplay" DRM attached.
I don't really know anything about removing Apple's DRM. There used to be software called Requiem that required an old version of iTunes to work and I'm told there is currently some commercial software that works, but I don't know the name. Of course forum rules here prohibit detailed discussion of DRM removal, but maybe someone on Apprentice Alf's blog would know the current methods, if any, for removing iBooks/Fairplay DRM.
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