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| Other names | Progesterone acetate; Progesterone 3-acetate; 3-Acetoxypregna-3,5-diene-20-one; 20-Oxopregna-3,5-dien-3-yl acetate; 3,5-Progesterol acetate; NSC-124740 |
| Drug class | Progestogen;Progestogen ether |
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| Chemical and physical data | |
| Formula | C23H32O3 |
| Molar mass | 356.506 g·mol−1 |
| 3D model (JSmol) | |
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Progesterone 3-acetyl enol ether, also known asprogesterone acetate,[1] as well as3-acetoxypregna-3,5-dien-20-one, is aprogestin which was never marketed.[2][3][4][5] It was reported to possess similarpotency toprogesterone andhydroxyprogesterone caproate in the rabbitendometrialcarbonic anhydrase test, abioassay ofprogestogenic activity.[2][3] In addition, it was able to maintainpregnancy in animals.[2] Progesterone 3-acetyl enol ether is closely related toquingestrone, which is also known as progesterone 3-cyclopentyl enol ether and was formerly marketed as anoral contraceptive.[6]
The 3-acetyl ether may becleaved from progesterone 3-acetyl enol etherin vivo and, based on itschemical structure, this may result in thetransformation of progesterone 3-acetyl enol ether into3α-dihydroprogesterone and/or3β-dihydroprogesterone. 3β-Dihydroprogesterone has been reported to possess about the sameprogestogenicpotency asprogesterone in theClauberg test, whereas 3α-dihydroprogesterone was not assessed.[7]
The C3 enol ethers of progesterone are less suited for use viadepot injection relative toprogestogen esters likehydroxyprogesterone caproate due to their susceptibility tooxidativemetabolism.[8]
An interesting substance which has received little attention is the 3-cyclopentyl enol ether of progesterone (quingestrone). [...]
In the Clauberg bioassay the 3β-hydroxy-4-pregnen-20-one shows about the same potency as progesterone (34). In regard to the biological activity of the 3α epimer no data are available.
Among a large no. of pregnane derivs. the esters of 17-α-hydroxyprogesterone (I), itself of weak lutein hormone action, have a strong and long-lasting gestagen action. The optimal results are obtained with I caproate. It permits the administration of depot doses in clear solns. Within the range of dosage used no androgenic effect was noted. It has no influence on growth and on the secondary sex characteristics in infantile and adult castrate male rats. The 3-enol esters of progesterone, which have a somewhat prolonged action, are less suited for depot administration because of their oxidizability.
