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Hi I'm Dr. Carole and I'm sorry to hear about Leo. I'm assuming he urinated outside the box, is that correct? It is possible he may have a urinary tract or bladder problem. He may have an infection that is causing him to have pain when he urinates and they associate that pain with the box so they go elsewhere looking for somewhere it doesn't hurt to urinate. Cats can also get what is called Idiopathic Cystitis which can look just like an infection with pain on urination and sometimes bloody urine but it is caused by an inflammation in the bladder wall and NOT an infection. Where antibiotics would be used to treat the infection the cystitis is treated with fluids and pain medications. Sometimes cats can get bladder or kidney stones that cause an infection and pain, that may need special diet or surgery to treat. Unfortunately male cats can sometimes develop a urinary tract blockage from mucous or crystals associated with these diseases that is a medical emergency and those cats need to have a urinary catheter placed and kept in the hospital for fluids. So if he can't urinate at all he needs to be seen ASAP!
I would suggest taking him to the vet for a urine test to diagnose the problem and get him appropriate treatment. They will likely get the sample by a process called Cystocentesis where they remove the urine directly from the bladder with a needle. This assures you get a sterile sample so if bacteria is present it means there is an infection.
I hope this helps. If I can answer any other questions please let me know. Otherwise please provide a rating so I can get credit for my response. Thanks
Oh Ok well for future knowledge you know all about urine issues in cats. If he had blood in the stool he may have a colitis or inflammation in the colon. It can make for painful defecation so same holds true, if it hurts to poop look for somewhere it doesn't hurt. In some cases the problem stems from a bacterial overgrowth and will need antibiotics. Sometimes is parasites. I recommend bringing in a fecal sample to the vet to check for both things. In the meantime try to give some fiber in the diet. Either metamucil mixed with the food or some canned pumpkin (cats usually love this). Make sure you keep the box clean, at least twice a day scoop the feces and urine and until he feels better consider adding a second box. There has been no changes with the box location or litter right?
Ah OK so the blood was probably due to stress (stress will cause a colitis very commonly). How many cats are in the house currently and how many boxes?
Ok for now I would suggest adding another box and maybe keeping the "problem child" confined to a small area with his own box. Do the fiber supplements for the colitis so he is not painful when defecating and make sure he has the same litter in the box as he is used to. If he is not better take in the stool for examination in case he needs medications to treat a bowel problem.
It was my pleasure, glad I could be of help. I would be very appreciative if you could provide a rating so I can get credit for my answer. Thanks