Yes it is possible for an infection to clear up the first time with an antibiotic, it's possible to have the same symptoms but have an entirely different infection; however if the infection persists, it is probably in your best interest to have a "Urine Culture & Sensitivity" performed on your pet's urine. This test is a little pricey ($70-100) but it will determine which organism(s) your pet may have in its urine and which antibiotic(s) will treat it and work. I say organismS (plurally) because your pet may have 1 or more DIFFERENT organisms plaguing her; and while one antibiotic may kill one organism it may or may not affect the other. As far as Cushing's Disease is concerned, here is a website that can give you a little more insight on any disease: www.veterinarypartner.com,
"Because of the immunosuppression associated with Cushing’s disease, evidence of bacterial infection may be present as well or such evidence may be concealed by the dilution of the urine. Ideally urine should be CULTURED if it is too dilute to reliably detect white blood cells or blood. Recent studies have shown that 20% of dogs with Cushing’s disease have an inapparent bladder infection." <== that is probably why your doctor suspect's Cushings.
What other symptoms does she have, such as excessive peeing, drinking tons of water, weakness in back legs, big belly, etc. Those are some of the symptoms of Cushings.