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Hello, my name is***** am a small animal veterinarian. I'm currently typing up my reply. This may take a few minutes. Thank you for your patience.
I am sorry to hear that Dexter has been having trouble urinating. There can be a number of causes for this to occur in dogs, the most common problem is a physical obstruction of the urethra with a urinary stone. Other causes can include swellings that obstruct the urethra - could be due to infection/inflammation or a growth, inability of the kidneys to produce urine due to underlying kidney damage, or a functional problem with the bladder that is preventing normal urination - can be due to nerve or muscle problems.
Ultimately it is very concerning that Dexter cannot pass urine at all. When dogs cannot empty their bladder of urine the electrolytes and other substances that are supposed to be urinated out can instead be absorbed back into the blood stream this can cause dogs to deteriorate very rapidly since these substances can affect heart function. The other big problem that can develop when pets cannot urinate is that the pressure builds up and this pressure can cause kidney damage. In very bad cases these problems can be extremely serious. It doesn't sound like Dexter is showing symptoms of these problems yet, but it is very important to have him examined by your local veterinarian or emergency clinic ASAP so that they can examine him and work towards getting him to urinate again. The sooner he is treated the lower the risk of further decline, this will allow Dexter to recover more quickly and it will likely cost less to treat as there won't be as many problems to fix.
Once you veterinarian examines Dexter they may suggest further testing e.g. blood tests that will check his kidneys and electrolyte levels, a blood cell panel to look for white and red cell changes, an abdominal x-ray and/or ultrasound to check for stones or other swellings. A urine test is very important too to look for signs of infections or crystals, the vet will likely be able to obtain urine by using a needle and syringe.
I wish you and Dexer the best of luck. Please let me know if you have any follow up questions, I will be happy to answer them.
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