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Metformin has acid dissociation constant values (pK<sub>a</sub>) of 2.8 and 11.5, so it exists very largely as the hydrophilic cationic species at physiological pH values. The metformin pK<sub>a</sub> values make it a stronger base than most other basic medications with less than 0.01% nonionized in blood. Furthermore, the [[Lipophilicity|lipid solubility]] of the nonionized species is slight as shown by its low logP value (log(10) of the distribution coefficient of the nonionized form between octanol and water) of −1.43. These chemical parameters indicate low lipophilicity and, consequently, rapid passive diffusion of metformin through cell membranes is unlikely. As a result of its low lipid solubility it requires the [[Membrane transport protein|transporter]] [[SLC22A1]] in order for it to enter cells. The logP of metformin is less than that of [[phenformin]] (−0.84) because two methyl substituents on metformin impart lesser lipophilicity than the larger phenylethyl side chain in [[phenformin]]. More lipophilic derivatives of metformin are presently under investigation with the aim of producing prodrugs with superior oral absorption than metformin.

Translations:Metformin/47/en - Revision history

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