{{Short description|Steroidal progestin drug}} {{About|a non-clinically used progestin compound|the pharmaceutical drug|medroxyprogesterone acetate}} {{Drugbox | IUPAC_name = (6''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1''H''-cyclopenta[''a'']phenanthren-3-one | image = Medroxyprogesterone.svg | image_class = skin-invert-image | width = 225px | image2 = Medroxiprogesterona3D.png | image_class2 = bg-transparent | width2 = 225px
<!--Clinical data--> | tradename = | pregnancy_category = | legal_status = | routes_of_administration = | class = Progestin; Progestogen
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | 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
<!--Chemical data--> | 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.<ref name="Elks2014">{{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–}}</ref><ref name="IndexNominum2000">{{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–}}</ref><ref name="MortonHall1999">{{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–}}</ref><ref name="Drugs.com">{{Cite web | url=https://www.drugs.com/international/medroxyprogesterone.html | title=Medroxyprogesterone}}</ref> A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.<ref name="Merck">{{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 }}</ref> ''Medroxyprogesterone'' is sometimes used as a synonym for ''medroxyprogesterone acetate'',<ref name = Merck/> and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.<ref name="pmid1119869">{{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 }}</ref>
==Pharmacology== ===Pharmacodynamics=== Compared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen.<ref name="pmid16784762">{{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 }}</ref> Medroxyprogesterone is also notable in that it is a minor metabolite of MPA.<ref name="pmid1271819">{{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 }}</ref> In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen ''in vitro'' on human androgen receptor.<ref>{{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 }}</ref>
{| class="wikitable sortable mw-collapsible mw-collapsed" style="width:425px; text-align:left; margin-left:auto; margin-right:auto; border:none;" |+ class="nowrap" | MP and related steroids at the PR (nM)<ref name="pmid16784762" /> |- ! Compound !! {{abbr|K<sub>i</sub>|Inhibitory constant}} !! {{abbrlink|EC<sub>50</sub>|Half-maximal effective concentration}}<sup>a</sup> !! {{abbr|EC<sub>50</sub>|Half-maximal effective concentration}}<sup>b</sup> |- | 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; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | Values are nM. <sup>a</sup> = Coactivator recruitment. <sup>b</sup> = 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.<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position.<ref name="Elks2014" /><ref name="IndexNominum2000" /> 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.<ref name="Elks2014" /><ref name="IndexNominum2000" />
==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}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" />
'''Brand Name'''
Meprate 10 Tablets (practo)
== References == {{Reflist}}
{{Progesterone receptor modulators}}
Category:Abandoned drugs Category:Tertiary alcohols Category:Alkene derivatives Category:Diketones Category:Pregnanes Category:Progestogens