Sorry, I was considering short things like dates and numbers as identifiers. I realize that's not quite right -- what I should have said was that indexes are designed for short things period (short identifiers being one of those things). Thanks.
> This fails when you need to insert new values into the table.
Yes, that's part of the extra code you need to keep the values accurately sorted. There are a lot of different particular code solutions that might work -- whether allowing for collisions and re-ordering every night with a cron job, or putting large gaps between numbers, or using floats.
But my main point stands, which is that standard relational databases are not designed to be able to maintain a sorted index of long URL's out of the box. Indexes aren't meant for that and they won't work, and this is by design. You're going to have to roll your own code for that.
Fortunately I've never come across a case in the wild where maintaining a globally sorted list of long items was required (though I'm not saying they never exist). E.g. if you're building a spider that needs to match against URL's, you'd index a short hash of the URL as a non-unique index. Or if you wanted to display sorted URL's for a site, you'd index by domain name only, and then sort the remainder of the URL at query time.