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Progesterone carboxymethyloxime

Chemical compound From Wikipedia, the free encyclopedia

Progesterone carboxymethyloxime
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Progesterone carboxymethyloxime, or progesterone 3-(O-carboxymethyl)oxime (P4-3-CMO), is a progestin which was never marketed.[1][2][3] It is an oral prodrug of progesterone with improved pharmacokinetic properties.[1] The compound was developed in an attempt to address the poor oral pharmacokinetics of progesterone, including its very low bioavailability and short biological half-life.[1][2] These properties of progesterone are thought to be caused by its low water solubility and high metabolic clearance rate due to rapid degradation in the intestines and liver.[1][2] Drugs with low aqueous solubility are not absorbed well in the intestines because their dissolution in water is limited.[4]

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P4-3-CMO (as the potassium salt) showed water solubility that was increased by more than four orders of magnitude relative to progesterone (solubility = 9.44 mol/L and 0.0006 mol/L, respectively).[2] In addition, it showed an in vitro terminal half-life in rat liver microsomes that was 363-fold longer than that of progesterone (half-life = 795.5 minutes and 2.2 minutes, respectively).[1] As such, P4-3-CMO could have both improved absorption and increased metabolic stability relative to progesterone.[1][2] However, the compound has not been further assessed nor studied in humans.[1][2]

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