Undecanoate

Undecanoate refers to esters or salts derived from undecanoic acid, a saturated carboxylic acid with an 11-carbon chain. In chemistry and pharmacology, undecanoate denotes the undecanoate ester of another molecule, formed by attaching the undecanoic acid moiety to an alcohol or to the parent drug. The resulting esters are typically highly lipophilic, reflecting the long hydrophobic chain of undecanoic acid, and are often used to create long-acting prodrugs.

In pharmaceutical contexts, undecanoate esters are valued for slow hydrolysis and extended release of the active compound. A well-known example is testosterone undecanoate, the undecanoate ester of testosterone, which serves as a long-acting prodrug in hormone replacement therapy or related treatments. The lipophilicity of undecanoate esters influences their absorption, distribution, and rate of enzymatic cleavage to release the active drug and undecanoic acid.

Beyond testosterone, undecanoate derivatives have been explored or employed to prolong the activity of various lipophilic drugs, particularly steroids. The pharmacokinetic behavior of undecanoate esters depends on the site and rate of ester hydrolysis by bodily esterases, as well as formulation factors that affect tissue uptake and release.

Safety and regulatory considerations for undecanoate-containing formulations align with those of the parent drug. As with other long-acting hormone or lipid-based prodrugs, potential risks include effects related to the active agent and, in some cases, issues related to prolonged exposure. Clinical use requires appropriate medical supervision and dosing.

See also: Decanoate, ester, prodrug.