Poor Pablo. Infected fold

It will take while for the hair to grow back. His tear staining is a sign of some sort of allergy. Have you tried isolating the cause of the runny eyes? Food? Seasonal allergies? I'd try Benadryl first and see if that helps. One pill daily with breakfast and dinner to start. That can be easily increased to two pills twice daily.

Also, you can get rid of those tear stains in a couple of weeks with Tylan powder. Once daily...1/8th Teaspoon with breakfast for 2-3 weeks and it's usually gone.
 
I thought the tear stains are just from the water. We've been feeding him fromm puppy pink bag up until recently now on grain free fromm. I haven't tired to isolate, thought it was the water.

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I would try to save tylosin antibiotic for more serious conditions such as chronic diarrhea then to use it for tear stains. I would use filtered water, ceramic or stainless steel water bowl only, make sure pet's food allergies are under control, and wash the dog's face near the eyes with some boric acid eye solution eg. collyrium or make your own. I read this formula on one web site:

Add one tablespoon Boracic Acid to a cup of boiling water, mix well. Place several cotton swabs into a plastic container. Pour the cooled solution over the swabs and seal the container. Use one swab daily to clean away tear and face staining. Make up a new mix at least once weekly.
 
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