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Pivaloyloxymethyl (POM, pivoxil, pivoxyl) is a
Pivaloyloxymethyl (POM, pivoxil, pivoxyl) is a protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis.
In man ...
used in organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.''Protective Groups in Organic Synthesis'', 3rd Edition, Theodora M. Greene and Peter G. M. Wuts, The POM radical
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has the formula (CH3)3C-CO-O-CH2.
The POM group is also sometimes used to produce prodrugs. For example, the POM group can be attached to a negatively charged organophosphate
In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered ...
group(s) of a drug causing a neutralization of the negative charge, which can allow the drug to become more lipid-soluble
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipoph ...
and thus more able to diffuse passively across cell membrane
The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of all cells from the outside environment (the ...
s 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 include adefovir dipivoxil
Adefovir is a prescription medicine used to treat (chronic) infections with hepatitis B virus. A prodrug form of adefovir was previously called bis-POM PMEA, with trade names Preveon and Hepsera. It is an orally administered nucleotide analog reve ...
, pivampicillin, cefditoren pivoxil, pivmecillinam
Pivmecillinam (INN) or amdinocillin pivoxil ( USAN, trade names Selexid, Penomax and Coactabs) is an orally active prodrug of mecillinam, an extended-spectrum penicillin antibiotic. Pivmecillinam is the pivaloyloxymethyl ester of mecillinam.
...
, and valproate pivoxil. Tenofovir disoproxil
Tenofovir disoproxil, sold under the trade name Viread among others, is a medication used to treat chronic hepatitis B and to prevent and treat HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for preven ...
contains a very similar prodrug group.
See also
*Pivalic acid
Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (''t''-BuC(O)) is Piv and for pivalic acid ...
References
{{reflist Protecting groups Carboxylate esters