What sort of medication did he get, if you don't mind my asking?
I'm suspecting ulcers in my girl, so I'm just trying to research!
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I have a thread that I started when I first started thinking it was ulcer that has what I've been doing here : Cinny's Ulcer Thread
A lot of my information I found here: stomach ulcers in horses and hind gut ulcers
Mostly I have been giving him the 1/4 tube of Ulcer Guard a day, but the vet is switching us to the Rantidine to do an actual treatment as it's much much cheaper than the gastroguard/ulcerguard treatment by about 900 bucks.
The most important thing I have found to make him comfortable for rides, I found in the article and my vet agrees with it. Fill your horse's stomach before the ride. I have found that giving him 2 cups of alfalfa pellets (the only alfalfa in his diet) with about 25 tums as I'm prepping him for our ride makes a HUGE difference right now. My vet says later into the treatment it won't matter as much but it will always be a good idea to try to keep something in his tummy all day.
He also said to try something called a Nibblenet, which I found here...The NIBBLENET ® Slow Feeder Hay Bags - thenibblenet.com - Official website of The NIBBLENET ® Slow feeder Hay Bag - Slow Feed Hay Bags for Horses
but they are a little pricey for me after everything else. It looks AWESOME though because your horse nibbles it's hay all day keeping something in it's stomach and he says that the saliva neutralizes stomach acid, another reason you want them to nibble all day.
Hope this helps, I'll be keeping updates on Cin's ulcer thread, I just posted the vid separate so that people who saw him be a jerk in my show vids can see how different he is now as some thought it was a training/back to basics issue. I do agree, we have basics to get back to, especially in my equitation, I am just happy we don't have to rewind quite so far.