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Hello, I'm Dr Gary. I've been practicing veterinary medicine since 2007. I look forward to helping with your questions/ concerns.
It sounds like he is having some pain as he tries to pass this. I wish there was a quick fix, but you kind of just have to let it pass on it's own.
Bones will get digested nicely in the stomach. The problem is that it gets digested down to a sand type consistency. This will irritate the lining of the intestine as it moves through. Once in the colon, it can lead to some irritation and bleeding.
To help it pass, I like to give extra fiber and a laxative. As a fiber source, you can give 1-2 teaspoons of canned pumpkin 2-3 times daily. As a laxative, you can pick up laxatone at a pet store and give a small amount 1-2 times daily. Alternatively, you could give Miralax- 1/4 teaspoon 1-2 times daily.
I hope this helps, let me know if you have any other questions.