Generally, prepaid medical expenses, including dental costs, are not deductible. An old Tax Court case said that advance payment for medical services to be rendered in the following year are not deductible in the year paid. The only exception is for prepaid of lifetime care from a continuing care facility or nursing home.
An employer reimbursement or allowance arrangement that requires you to adequately substantiate business expenses to your employer, and to return any excess reimbursement.