IMHO, you've got a LOT of redundancy. Not necessarily a bad thing, but if you've got to move that distance, perhaps it's best to skip some:
-Ditch the pillow. Attatch the blanket roll to the bottom of your bag. Might make for a more comfortable set-up.
- 5 water bottles? Might be lighter to buy bigger volume bottles (a 2-qt is probably lighter than 2 1-qt bottles)
- Aspirin, Tylenol, AND Aleve? They're all essentially the same thing. Slight chemical differences, similar indication for use. You also have more Aleve in your mess kit. Tylenol in your shave kit. Aspirin in your shave kit.
- Theraflu AND Tylenol Sinus? Ditto above.
- Q-tips? Nice, light, I'd ditch, but not big enough to argue if you like them.
- Just out of curiousity, how'd you come up with the numbers for condiments (19 sugar, 9 salt and pepper)?
- Moist towlettes in your messenger bag, and baby wipes in your ruck. You might be able to get away with one or the other.
- Rucksack, # 5,6,7 are repeats of #2,3,4.
- Your shaving kit is essentially a FAK. Do you need all of it again? Is shaving your first priority? Vitamin C, Chondroiton, multi-vitamins? Drop the baby Aspirin (unless you take daily!!!) and use regular aspirin. Or ditch the regular, and take 4 baby's to make the same dose.
- Clarinix and Alegra are both allergy pills. Why need both?
-How many spare batteries and bulbs do you need? You didn't mention size, which affects weight. If you go with an LED light, you can skip spare bulbs, and get away with minimal batteries.
- Ditto the monocular in place of binoculars. I'd probaby leave the camera too, unless it's really small.

So my suggestions probably don't cut much on weight, but maybe clear some space and lighten you a few pounds. Hope I'm not offending, but these are the first thoughts.