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| Clinical data | |
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| Other names | 11α-Methoxyethinylestradiol; 11α-Methoxy-17α-ethynylestradiol; 11α-Methoxy-19-nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17-diol |
| Routes of administration | By mouth[1] |
| Drug class | Estrogen;Estrogen ether |
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| CAS Number | |
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| ChemSpider | |
| UNII | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C21H26O3 |
| Molar mass | 326.436 g·mol−1 |
| 3D model (JSmol) | |
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RU-16117 is anestrogen medication which was investigated for the potential treatment ofsymptoms ofestrogen deficiency such ashot flashes andosteoporosis in women but was never marketed.[1] It was developed for useby mouth.[1]
RU-16117 is anestrogen, or anagonist of theestrogen receptor (ER).[1][2] Inmouseuterinetissue, it shows about 5 to 13% of theaffinity ofestradiol for the ER and about 1% of theestrogenic activity of estradiol.[2][3][4] Conversely, it shows no affinity for theandrogen,progesterone,glucocorticoid, andmineralocorticoid receptors, nor any activities associated with interactions with these receptors.[2][5][3][4] While the association rate of RU-16117 to the ER is the same as that ofmoxestrol, it dissociates from the ER extremely rapidly at rates of about three times faster than estradiol and about 20 times faster than moxestrol.[1][6] This is similar to the case ofestriol, which RU-16117 is described as sharing similarities with.[1][6] RU-16117 is described as a weak orpartial estrogen or a mixed estrogen/antiestrogen.[1][2] It has been described as having highly activeantiestrogenic activity with very weakuterotrophic activity.[7][2] However, higher doses and/or prolonged administration of RU-16117 have been reported to induce equivalent estrogenic responses relative to estradiol and moxestrol.[1][6]
| Compound | PRTooltip Progesterone receptor | ARTooltip Androgen receptor | ERTooltip Estrogen receptor | GRTooltip Glucocorticoid receptor | MRTooltip Mineralocorticoid receptor | SHBGTooltip Sex hormone-binding globulin | CBGTooltip Corticosteroid binding globulin | ||
|---|---|---|---|---|---|---|---|---|---|
| Estradiol | 2.6 | 7.9 | 100 | 0.6 | 0.13 | 8.7 | <0.1 | ||
| Estriol | ? | ? | 15 | ? | ? | ? | ? | ||
| Ethinylestradiol | 15–25 | 1–3 | 112 | 1–3 | <1 | ? | ? | ||
| Moxestrol (11β-MeO-EE) | 0.8 | <0.1 | 12 | 3.2 | <0.1 | <0.2 | <0.1 | ||
| RU-16117 (11α-MeO-EE) | 1–3 | <1 | 13 | <1 | <1 | ? | ? | ||
| Values are percentages (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,E2 for theERTooltip estrogen receptor,DEXATooltip dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,DHTTooltip dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip Corticosteroid-binding globulin. | |||||||||
RU-16117, also known as 11α-methoxy-17α-ethynylestradiol (11α-MeO-EE) or as 11α-methoxy-17α-ethynylestra-1,3,5(10)-triene-3,17β-diol, is asyntheticestranesteroid and aderivative ofestradiol.[1] It is specifically a derivative ofethinylestradiol (17α-ethynylestradiol) with amethoxy group at the C11α position.[1] The compound is the C11αisomer or C11epimer ofmoxestrol (11β-methoxy-17α-ethynylestradiol).[1][9]
RU-16117 is derived fromΔ9,11-dehydroestradiol [Wikidata] (1). Its two hydroxy groups are firstprotected by the formation ofbenzyl ethers, giving (2) and the isolated double bond is hydrated by hydroboration, followed by oxidation with hydrogen peroxide in alkali to give (3). The newly-introduced alcohol ismethylated withiodomethane to produce (4). After removal of the protecting groups bycatalytic hydrogenation to form (5), the hydroxyl group in the five-membered ring is oxidized to aketone withchromium trioxide and the product, (6), is reacted with potassium acetylide to introduce theacetylide group of the drug.[1][10]
