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| Clinical data | |
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| Other names | 9β,10α-Progesterone; 9β,10α-Pregn-4-ene-3,20-dione |
| Drug class | Progestin;Progestogen |
| ATC code |
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| Identifiers | |
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| CAS Number | |
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| ECHA InfoCard | 100.018.553 |
| Chemical and physical data | |
| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
| 3D model (JSmol) | |
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Retroprogesterone, also known as9β,10α-progesterone or as9β,10α-pregn-4-ene-3,20-dione, is aprogestin which was never marketed.[1][2] It is astereoisomer of thenaturally occurringprogestogenprogesterone, in which thehydrogen atom at the 9th carbon is in the α-position (below the plane) instead of the β-position (above the plane) and themethyl group at the 10th carbon is in the β-position instead of the α-position.[1][2] In other words, the atom positions at the two carbons have been reversed relative to progesterone, hence the nameretroprogesterone. This reversal results in a "bent" configuration in which the plane of rings A and B is orientated at a 60° angle below the rings C and D.[3] This configuration is ideal for interaction with theprogesterone receptor, with retroprogesterone binding with highaffinity to this receptor.[4] However, the configuration is not as ideal for binding to othersteroid hormone receptors, and as a result, retroprogesterone derivatives have increasedselectivity for the progesterone receptor relative to progesterone.[5]
Retroprogesterone is theparent compound of a group of progestins consisting of the marketed progestinsdydrogesterone (6-dehydroretroprogesterone) andtrengestone (1,6-didehydro-6-chlororetroprogesterone) and the never-marketed progestinRo 6-3129, as well as theactive metabolites of these progestins like 20α-dihydrodydrogesterone and 20α-dihydrotrengestone (i.e., the 20α-hydroxylatedanalogues).[1][2][6][7]
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