medroxyprogesterone
{{Short description|Steroidal progestin drug}}
{{About|a non-clinically used progestin compound|the pharmaceutical drug|medroxyprogesterone acetate}}
{{Drugbox
| IUPAC_name = (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
| image = Medroxyprogesterone.svg
| width = 225px
| image2 = Medroxiprogesterona3D.png
| width2 = 225px
| tradename =
| pregnancy_category =
| legal_status =
| routes_of_administration =
| class = Progestin; Progestogen
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 520-85-4
| CAS_supplemental =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = HSU1C9YRES
| ATC_prefix = None
| ATC_suffix =
| PubChem = 10631
| ChemSpiderID = 10185
| synonyms = MP; Methylhydroxyprogesterone; 6α-Methyl-17α-hydroxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-en-3,20-dione
| C=22 | H=32 | O=3
| SMILES = O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)C)CC[C@H]3[C@@H]1C[C@@H]2C)C)(C)CC4
| StdInChI = 1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1
| StdInChIKey = FRQMUZJSZHZSGN-HBNHAYAOSA-N
}}
Medroxyprogesterone (MP), is a progestin which is not used medically.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA657|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=657–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA638|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=638–}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=mqaOMOtk61IC&pg=PA173|date=31 October 1999|publisher=Springer Science & Business Media|isbn=978-0-7514-0499-9|pages=173–}}{{Cite web | url=https://www.drugs.com/international/medroxyprogesterone.html | title=Medroxyprogesterone}} A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.{{cite web | publisher = Merck Manual | url = http://www.merck.com/mmpe/lexicomp/medroxyprogesterone.html | title = MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp | access-date = 2010-07-08 | date = 2009-12-01 }} Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate, and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.{{cite journal | vauthors = Lenco W, Mcknight M, Macdonald AS | title = Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits | journal = Annals of Surgery | volume = 181 | issue = 1 | pages = 67–73 | date = January 1975 | pmid = 1119869 | pmc = 1343717 | doi = 10.1097/00000658-197501000-00015 }}
Pharmacology
=Pharmacodynamics=
Compared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen.{{cite journal | vauthors = Pullen MA, Laping N, Edwards R, Bray J | title = Determination of conformational changes in the progesterone receptor using ELISA-like assays | journal = Steroids | volume = 71 | issue = 9 | pages = 792–8 | date = September 2006 | pmid = 16784762 | doi = 10.1016/j.steroids.2006.05.009 | s2cid = 24703323 }} Medroxyprogesterone is also notable in that it is a minor metabolite of MPA.{{cite journal | vauthors = Ishihara M, Kirdani Y, Osawa Y, Sandberg AA | title = The metabolic fate of medroxyprogesterone acetate in the baboon | journal = Journal of Steroid Biochemistry | volume = 7 | issue = 1 | pages = 65–70 | date = January 1976 | pmid = 1271819 | doi = 10.1016/0022-4731(76)90167-9 }} In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen in vitro on human androgen receptor.{{cite journal | vauthors = Šauer P, Bořík A, Golovko O, Grabic R, Staňová AV, Valentová O, Stará A, Šandová M, Kocour Kroupová H | display-authors = 6 | title = Do progestins contribute to (anti-)androgenic activities in aquatic environments? | journal = Environmental Pollution | volume = 242 | issue = Pt A | pages = 417–425 | date = November 2018 | pmid = 29990947 | doi = 10.1016/j.envpol.2018.06.104 | bibcode = 2018EPoll.242..417S | s2cid = 51622914 }}
| class="wikitable sortable mw-collapsible mw-collapsed" style="width:425px; text-align:left; margin-left:auto; margin-right:auto; border:none;" | |||
| Compound | Binding affinity | {{abbrlink|EC50|Half-maximal effective concentration}}a | {{abbr|EC50|Half-maximal effective concentration}}b |
|---|---|---|---|
| Progesterone | 4.3 | 0.9 | 25 |
| Medroxyprogesterone | 241 | 47 | 32 |
| Medroxyprogesterone acetate | 1.2 | 0.6 | 0.15 |
| class="sortbottom"
| colspan="4" style="width: 1px;" | Values are nM. a = Coactivator recruitment. b = Reporter cell line. |
Chemistry
{{See also|List of progestogens}}
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. It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position. 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.
Society and culture
=Generic names=
Medroxyprogesterone is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}}.
Brand Name
Meprate 10 Tablets (practo)
References
{{Reflist}}
{{Progesterone receptor modulators}}