A medication dispensing system uses a series of medication rings grouped as a rotary drum and controlled for dispensing medication on a daily basis into a divided pill box. Each medication ring includes an associated medication collar that cooperates with the medication ring to reduce the possibility of abrasion of the medication dosages held in the medication rings. The pill box is moved and rotated within the dispensing system by a carriage to dispense medication into appropriate cells of the pill box. A computer control module controls the movement of the various components and is programmable for loading and dispensing different medication regimes.