A system comprising: a needle hub (26, 126, 226) having a proximal end (52, 152) and a distal end (50, 150), the proximal end (52, 152) of the needle hub (26, 126 226) having a connection portion configured to receive a first container; a cannula (20, 120, 120B) received by the needle hub (26, 126, 226), the cannula (20, 120, 120B) having a proximal end (32, 132) and a distal end (30, 130) and a lumen; a cannula seal (22, 122, 222) comprising a resilient sleeve enclosing at least a portion of the cannula (20, 120, 120B), the cannula seal (22, 122, 222) having an open proximal end (42, 142) and a distal end (40, 140), wherein the needle hub (26, 126, 226) and cannula seal (22, 122, 222) define a collapsible capsule having an interior cavity; and a vial adapter configured to be attached to a second container, the vial adapter having a vial seal (100, 100A) and a body, the vial seal (100, 100A) is configured to engage the cannula seal (22, 122, 222), the body of the vial adapter is configured to align with a septum (94, 94A) of the second container; wherein the cannula seal (22, 122, 222) has a first position where the cannula seal (22, 122) encloses the distal end (30, 130) of the cannula 20, 120, 120B) and a second position where the cannula seal (22, 122, 222) is engaged to the vial and is retracted to insert the distal end (30, 130) of the cannula (20, 120, 120B) and lumen to an interior of the vial, and further wherein the vial seal (100, 100A) of the vial adapter defines a recess that is configured to receive the distal end (40, 140) of the cannula seal (22, 122, 222), characterized in that the system further comprising an aspiration arrangement having a ring-shaped filter and a one-way valve disposed in the collapsible capsule the filter disposed between the interior cavity and an exterior of the collapsible capsule thereby allowing air to be aspirated through the filter and into the cannula lumen. a needle hub (26, 126, 226) having a proximal end (52, 152) and a distal end (50, 150), the proximal end (52, 152) of the needle hub (26, 126 226) having a connection portion configured to receive a first container; a cannula (20, 120, 120B) received by the needle hub (26, 126, 226), the cannula (20, 120, 120B) having a proximal end (32, 132) and a distal end (30, 130) and a lumen; a cannula seal (22, 122, 222) comprising a resilient sleeve enclosing at least a portion of the cannula (20, 120, 120B), the cannula seal (22, 122, 222) having an open proximal end (42, 142) and a distal end (40, 140), wherein the needle hub (26, 126, 226) and cannula seal (22, 122, 222) define a collapsible capsule having an interior cavity; and a vial adapter configured to be attached to a second container, the vial adapter having a vial seal (100, 100A) and a body, the vial seal (100, 100A) is configured to engage the cannula seal (22, 122, 222), the body of the vial adapter is configured to align with a septum (94, 94A) of the second container; wherein the cannula seal (22, 122, 222) has a first position where the cannula seal (22, 122) encloses the distal end (30, 130) of the cannula 20, 120, 120B) and a second position where the cannula seal (22, 122, 222) is engaged to the vial and is retracted to insert the distal end (30, 130) of the cannula (20, 120, 120B) and lumen to an interior of the vial, and further wherein the vial seal (100, 100A) of the vial adapter defines a recess that is configured to receive the distal end (40, 140) of the cannula seal (22, 122, 222), characterized in that the system further comprising an aspiration arrangement having a ring-shaped filter and a one-way valve disposed in the collapsible capsule the filter disposed between the interior cavity and an exterior of the collapsible capsule thereby allowing air to be aspirated through the filter and into the cannula lumen.