I've asked in the past about this (via support) and been told no. If you want to replace a file you need to upload the new one and deactivate the old one assuming the new was approved (and a note to the inspectors that it's a duplicate of image xxxxxx which will be deactivated upon approval will avoid it getting a rejection for being a duplicate).

What this means is you don't have your best match position or sales track record for the newly uploaded file.

In general, I'd just leave the old one as is and shoot something new.

About a year ago I had them replace ~20 files with updated versions. They did it no problems although it took them a few months. I just put them all in a zip folder and uploaded to my host and they took it from there.

It was one of the rare positive experiences with IS.