[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/18-methylsegesterone-acetate-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki40\/18-methylsegesterone-acetate-wikipedia\/","headline":"18-Methylsegesterone acetate – Wikipedia","name":"18-Methylsegesterone acetate – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia after-content-x4 Chemical compound 18-Methylsegesterone acetate Other names 18-Methyl-SGA; 13\u03b2-Ethyl-SGA; 18-Methylnestorone; 18-Methyl-NES; 13\u03b2-Ethylnestorone; 13\u03b2-Ethyl-NES; 18-Methylelcometrine;","datePublished":"2018-10-17","dateModified":"2018-10-17","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki40\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/b\/be\/18-Methylsegesterone_acetate.svg\/200px-18-Methylsegesterone_acetate.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/b\/be\/18-Methylsegesterone_acetate.svg\/200px-18-Methylsegesterone_acetate.svg.png","height":"158","width":"200"},"url":"https:\/\/wiki.edu.vn\/en\/wiki40\/18-methylsegesterone-acetate-wikipedia\/","wordCount":2893,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopedia       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Chemical compound18-Methylsegesterone acetateOther names18-Methyl-SGA; 13\u03b2-Ethyl-SGA; 18-Methylnestorone; 18-Methyl-NES; 13\u03b2-Ethylnestorone; 13\u03b2-Ethyl-NES; 18-Methylelcometrine; 16-Methylene-17\u03b1-acetoxy-18-methyl-19-norprogesterone; 16-Methylene-17\u03b1-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetateDrug classProgestin; Progestogen; Progestogen ester[(8R,9S,10R,13S,14S,17R)-17-Acetyl-13-ethyl-16-methylidene-3-oxo-2,6,7,8,9,10,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetatePubChem CIDChemSpiderFormulaC24H32O4Molar mass384.516\u00a0g\u00b7mol\u221213D model (JSmol)CC[C@]12CC[C@H]3[C@H]([C@@H]1CC(=C)[C@@]2(C(=O)C)OC(=O)C)CCC4=CC(=O)CC[C@H]34       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4InChI=1S\/C24H32O4\/c1-5-23-11-10-20-19-9-7-18(27)13-17(19)6-8-21(20)22(23)12-14(2)24(23,15(3)25)28-16(4)26\/h13,19-22H,2,5-12H2,1,3-4H3\/t19-,20+,21+,22-,23-,24-\/m0\/s1Key:YIAUAVGJQYAQFE-ZUYVPRDGSA-N18-Methylsegesterone acetate (18-methyl-SGA; also known as 18-methylnestorone) is a progestin medication of the 19-norprogesterone group which was never marketed.[1][2][3] It was first described in a patent in 1997 and then in a literature paper in 2003.[4][1] 18-Methyl-SGA is the C18 methyl or C13\u03b2 ethyl derivative of segesterone acetate (SGA; 16-methylene-17\u03b1-acetoxy-19-norprogesterone), and shows 3 to 10\u00a0times the progestogenic potency of SGA in bioassays.[1] This is analogous to the case of the 19-nortestosterone progestin norethisterone and its 18-methyl derivative levonorgestrel, the latter showing substantially increased potency relative to the former similarly.[1] As SGA is already one of the most potent progestins to have been developed, with 100-fold the potency of progesterone and 10-fold the potency of levonorgestrel in bioassays, 18-methyl-SGA is an extremely potent progestogen, among if not the most potent known.[2][5][1]SGA is a highly selective progestogen.[1][5] Like SGA, 18-methyl-SGA shows negligible affinity for the androgen receptor.[1][3] While 18-methyl-SGA has not been assessed at the other steroid hormone receptors, it is expected to be highly selective for the progesterone receptor similarly to SGA.[1] 18-Methyl-SGA shows over 16\u00a0times the affinity of progesterone for the progesterone receptor expressed in rat uterus.[1] In terms of oral bioavailability, it is known that SGA is not active orally, while the oral activity of 18-methyl-SGA is unknown.[1] The addition of an 18-methyl group to SGA is unlikely to affect its rate of delivery from sustained release systems.[1] As such, 18-methyl-SGA should be ideally suited for use via routes of administration like subcutaneous implants and transdermal patches.[1]       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4See also[edit]References[edit]^ a b c d e f g h i j k l m Tuba Z, Bardin CW, Dancsi A, Francsics-Czinege E, Moln\u00e1r C, Cs\u00f6rgei J, Falkay G, Koide SS, Kumar N, Sundaram K, Duk\u00e1t-Abr\u00f3k V, Balogh G (May 2000). “Synthesis and biological activity of a new progestogen, 16-methylene-17alpha-hydroxy-18-methyl-19-norpregn-4-ene-3, 20-dione acetate”. Steroids. 65 (5): 266\u201374. doi:10.1016\/S0039-128X(99)00109-9. PMID\u00a010751638. S2CID\u00a037188669.^ a b Sitruk-Ware R, Small M, Kumar N, Tsong YY, Sundaram K, Jackanicz T (November 2003). “Nestorone: clinical applications for contraception and HRT”. Steroids. 68 (10\u201313): 907\u201313. doi:10.1016\/S0039-128X(03)00140-5. PMID\u00a014667982. S2CID\u00a034984413.^ a b Kumar N, Fagart J, Liere P, Mitchell SJ, Knibb AR, Petit-Topin I, Rame M, El-Etr M, Schumacher M, Lambert JJ, Rafestin-Oblin ME, Sitruk-Ware R (January 2017). “Nestorone as a Novel Progestin for Nonoral Contraception: Structure-Activity Relationships and Brain Metabolism Studies”. Endocrinology. 158 (1): 170\u2013182. doi:10.1210\/en.2016-1426. PMC\u00a05412978. PMID\u00a027824503.^ 18-methyl 16-methylene 19-nor pregnane derivatives as progestins, pharmaceutical compositions containing them and process for the preparation thereof. https:\/\/patents.google.com\/patent\/WO1997023498A1\/en^ a b Kumar N, Koide SS, Tsong Y, Sundaram K (2000). “Nestorone: a progestin with a unique pharmacological profile”. Steroids. 65 (10\u201311): 629\u201336. doi:10.1016\/S0039-128X(00)00119-7. PMID\u00a011108869. S2CID\u00a013722269.PRAgonistsTestosterone derivatives: Progestins: 6,6-Difluoronorethisterone6,6-Difluoronorethisterone acetate17\u03b1-Allyl-19-nortestosteroneAllylestrenolAltrenogestChloroethynylnorgestrelCingestolDanazolDesogestrelDienogestEthinylandrostenediolEthisteroneEthyneroneEtonogestrelEtynodiolEtynodiol diacetateGestodeneGestrinoneLevonorgestrelLevonorgestrel esters (e.g., levonorgestrel butanoate)LynestrenolLynestrenol phenylpropionateMetynodiolMetynodiol diacetateNorelgestrominNorethisterone (norethindrone)Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)NoretynodrelNorgesteroneNorgestimateNorgestrelNorgestrienoneNorvinisteroneOxendoloneQuingestanolQuingestanol acetateTiboloneTigestolTosagestin; Anabolic\u2013androgenic steroids: 11\u03b2-Methyl-19-nortestosterone11\u03b2-Methyl-19-nortestosterone dodecylcarbonate19-Nor-5-androstenediol19-Nor-5-androstenedione19-NordehydroepiandrosteroneBolandiolBolandiol dipropionateBolandioneDimethisteroneDienedioneDienoloneDimethandroloneDimethandrolone buciclateDimethandrolone dodecylcarbonateDimethandrolone undecanoateDimethyldienoloneDimethyltrienoloneEthyldienoloneEthylestrenol (ethylnandrol)MethyldienoloneMetribolone (R-1881)Methoxydienone (methoxygonadiene)MiboleroneNandroloneNandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)NorethandroloneNormethandrone (methylestrenolone, normethandrolone, normethisterone)RU-2309TetrahydrogestrinoneTrenbolone (trienolone)Trenbolone esters (e.g., trenbolone acetate, trenbolone enanthate)TrendioneTrestoloneTrestolone acetateMixed(SPRMs)AntagonistsmPR(PAQR)     (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4"},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/18-methylsegesterone-acetate-wikipedia\/#breadcrumbitem","name":"18-Methylsegesterone acetate – Wikipedia"}}]}]