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I wonder if he has a malabosorbtion problem. Sounds like he is not absorbing nutrients from the food he is eating. Get a lab work up on him. I would seriously change his diet and ask your vet about purchasing a supplement called pancreazyme. It is for pancreatitis but it will help him absorb nutrients from the food he eats and he will gain weight. It is safe to use even if he doesn’t have pancreatitis. Pancreazyme is pricey but well worth it and the best product to use. He needs to be on a much better diet. Diet is MEDICINE for pets and for people. Try Halo dog food. I highly recommend it! Introduce it slowly with cooked chicken and cooked pasta – make sure it is very soft. (easy to digest) Feed him three times a day – 1 1/4 cups three times a day, use 1/2 cup dry and the rest chicken and pasta and slowly make a transition to feeding him twice a day. He needs 2 cups of food twice a day once he is back to normal. The protein i look for in a pet food for a large dog is: Crude Protein 28% (Min), Crude Fat 12% (Min), or Crude Protein 28% (Min), Crude Fat 16% (Min) Halo dog food has the correct protein/fat ratios. I would recommend the turkey and duck to start with because it has less fat, not knowing if the fat content in the food he is eating is causing him to have problems. Trust me this is the best food out there!