I see you are concerned that your son has recurrent croup. Croup is usually caused by one of many viruses that cause constriction and swelling of the upper airway, usually below the voice box. This manifests as a harsh cough that sounds like a dog or seal bark as well as a noise when the child breathes in that is called a stridor. It is indeed unusual for croup to manifest as frequently as you describe. In my experience asthma can manifest as recurrent croup episodes. Also an allergic component may also be involved. Your doctors are already thinking along these lines because I see the medications they have prescribed are covering these specific entities.
You do not state as to whether your child responds acutely to these medications. If he does, then he should be continuing these as a daily maintenance to prevent rather than just treat acute episodes. If he does respond to appropriate doses of the mentioned medications, his condition is most likely non-contagious and he can attend day care if he feels well.
If your child gets no relief at all from these medicines, your doctors may want to consider some imaging studies and an Ear Nose and Throat Specialist evaluation to see if there is an underlying lesion in his upper airway, or a vocal cord abnormality that may be predisposing him to manifest croupy symptoms, with even routine URI’s (colds). If your child has a history of spitting up or reflux, you might have your doctors consider this as a contributory factor and see if treatment for reflux relieves his symptoms.
Good luck, LJGMD
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