Pivaloyloxymethyl (POM,pivoxil,pivoxyl) is aprotecting group used inorganic synthesis.[1] The POMradical has the formula (CH3)3C-CO-O-CH2.
The POM group is also sometimes used to produceprodrugs. For example, the POM group can be attached to a negatively chargedorganophosphate group(s) of a drug causing a neutralization of the negative charge, which can allow the drug to become morelipid-soluble and thus more able to diffuse passively acrosscell membranes into cells. Upon entry into cells, the POM portion of the molecule can be removed by cellular processes resulting in release of active drug.
Clinically used prodrugs containing pivaloyloxymethyl groups includeadefovir dipivoxil,pivampicillin,cefditoren pivoxil,pivmecillinam, andvalproate pivoxil.Tenofovir disoproxil contains a very similar prodrug group.