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| Clinical data | |
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| Other names | P4-3-CMO; Progesterone 3-carboxymethyloxime; Progesterone 3-(O-carboxymethyl)oxime; 3-(O-Carboxymethyl-oximino)progesterone; [[(20-Oxopregn-4-en-3-ylidene)amino]oxy]acetic acid |
| Routes of administration | By mouth [1] |
| Drug class | Progestogen; Neurosteroid |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.164.875 |
| Chemical and physical data | |
| Formula | C23H33NO4 |
| Molar mass | 387.520 g·mol−1 |
| 3D model (JSmol) | |
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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]
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]
