Medroxyprogesterone
Steroidal progestin drug
From Wikipedia, the free encyclopedia
Medroxyprogesterone (MP), is a progestin which is not used medically.[1][2][3][4] A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.[5] Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,[5] and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.[6]
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| Other names | MP; Methylhydroxyprogesterone; 6α-Methyl-17α-hydroxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-en-3,20-dione |
| Drug class | Progestin; Progestogen |
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| ECHA InfoCard | 100.007.545 |
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| Formula | C22H32O3 |
| Molar mass | 344.495 g·mol−1 |
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Pharmacology
Pharmacodynamics
Compared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen.[7] Medroxyprogesterone is also notable in that it is a minor metabolite of MPA.[8] In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen in vitro on human androgen receptor.[9]
| Compound | Ki | EC50a | EC50b |
|---|---|---|---|
| Progesterone | 4.3 | 0.9 | 25 |
| Medroxyprogesterone | 241 | 47 | 32 |
| Medroxyprogesterone acetate | 1.2 | 0.6 | 0.15 |
| Values are nM. a = Coactivator recruitment. b = Reporter cell line. | |||
Chemistry
Medroxyprogesterone, also known as 6α-methyl-17α-hydroxyprogesterone or as 6α-methyl-17α-hydroxypregn-4-en-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone.[1][2] It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position.[1][2] The generic name of medroxyprogesterone is a contraction of 6α-methyl-17α-hydroxyprogesterone. It is closely related to medrogestone as well as other unesterified 17α-hydroxyprogesterone derivatives such as chlormadinone, cyproterone, and megestrol.[1][2]