A vial adapter for side engagement of a vial cap includes a needleless connector having a housing and defining one or more fluid pathways therein an elongated piercing spike operatively coupled to the needleless connector, the elongated piercing spike having a longitudinal axis and one or more channels for fluid connectivity with the one or more fluid pathways at least one housing arm coupled to the housing and extending parallel to the longitudinal axis and a coupling member configured to orthogonally receive a vial cap with respect to the longitudinal axis, the coupling member having a planar surface, an aperture of the planar surface longitudinally aligned with the elongated piercing spike, and at least one support arm extending from the planar surface operatively coupled with the at least one housing arm to allow relative longitudinal movement between the coupling member and the elongated piercing spike.
