Medroxyprogesterone (MP), is a progestin which is not used medically.[2][3][4][5] A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.[6] Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,[6] and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.[7]
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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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| Identifiers | |
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| ECHA InfoCard | 100.007.545 |
| Chemical and physical data | |
| Formula | C22H32O3 |
| Molar mass | 344.495 g·mol−1 |
| 3D model (JSmol) | |
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Pharmacology
editPharmacodynamics
editCompared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen.[8] Medroxyprogesterone is also notable in that it is a minor metabolite of MPA.[9] In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen in vitro on human androgen receptor.[10]
| 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
editMedroxyprogesterone, 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.[2][3] It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position.[2][3] 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.[2][3]
Society and culture
editGeneric names
editMedroxyprogesterone is the generic name of the drug and its INN and BAN.[2][3][5]
Brand Name
Meprate 10 Tablets (practo)
References
edit- ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
- ^ a b c d e Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 657–. ISBN 978-1-4757-2085-3.
- ^ a b c d e Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 638–. ISBN 978-3-88763-075-1.
- ^ Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 173–. ISBN 978-0-7514-0499-9.
- ^ a b "Medroxyprogesterone".
- ^ a b "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08.
- ^ Lenco W, Mcknight M, Macdonald AS (January 1975). "Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits". Annals of Surgery. 181 (1): 67–73. doi:10.1097/00000658-197501000-00015. PMC 1343717. PMID 1119869.
- ^ a b Pullen MA, Laping N, Edwards R, Bray J (September 2006). "Determination of conformational changes in the progesterone receptor using ELISA-like assays". Steroids. 71 (9): 792–8. doi:10.1016/j.steroids.2006.05.009. PMID 16784762. S2CID 24703323.
- ^ Ishihara M, Kirdani Y, Osawa Y, Sandberg AA (January 1976). "The metabolic fate of medroxyprogesterone acetate in the baboon". Journal of Steroid Biochemistry. 7 (1): 65–70. doi:10.1016/0022-4731(76)90167-9. PMID 1271819.
- ^ Šauer P, Bořík A, Golovko O, Grabic R, Staňová AV, Valentová O, et al. (November 2018). "Do progestins contribute to (anti-)androgenic activities in aquatic environments?". Environmental Pollution. 242 (Pt A): 417–425. Bibcode:2018EPoll.242..417S. doi:10.1016/j.envpol.2018.06.104. PMID 29990947. S2CID 51622914.