Ethinylandrostenediol

Ethinylandrostenediol
Clinical data
Other namesSKF-2856; 17α-Ethynyl-5-androstenediol; 17α-Ethynylandrost-5-ene-3β,17-diol; 17α-Pregn-5-en-20-yne-3β,17-diol; NSC-17098
Drug classEstrogen; Progestogen; Progestin
Identifiers
  • (3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O
  • InChI=1S/C21H30O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,5,15-18,22-23H,6-13H2,2-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1
  • Key:VGJUOWGYQZYCII-TVWVXWENSA-N

Ethinylandrostenediol (developmental code name SKF-2856), also known as 17α-ethynyl-5-androstenediol, is a synthetic estrogen, progestogen, and androgen which was never marketed.[1][2][3][4][5][6] It is the C17α ethynyl derivative of the androgen precursor and prohormone 5-androstenediol.[1]

Ethinylandrostenediol was first synthesized in the late 1930s and along with its close analogue ethisterone (17α-ethynyltestosterone) was one of the first progestins (synthetic progestogens) to be developed.[7][8][9] Ethinylandrostenediol is orally active similarly to ethisterone and shows about half its progestogenic potency.[9] Ethinylandrostenediol was an intermediate in the initial synthesis of ethisterone.[10]

Ethinylandrostenediol shows tissue selectivity in its estrogenic effects in animals and doesn't seem to have estrogenic effects in the uterus.[1] The androgenic activity of ethinylandrostenediol is weak.[9]

An ester of ethinylandrostenediol, ethandrostate (17α-ethynyl-5-androstenediol 3β-cyclohexylpropionate), has been studied clinically in men and women with prostate cancer and breast cancer, respectively.[11][12][13][14][15]

Notable structural analogues of ethinylandrostenediol include 5-androstenediol, 17α-ethynyl-3β-androstanediol, 17α-ethynyl-3α-androstanediol, ethisterone (17α-ethynyltestosterone), and methandriol (17α-methyl-5-androstenediol), as well as ethinylestradiol (17α-ethynylestradiol or 17α-ethynylestra-1,3,5(10)-triene-3,17β-diol).

Affinities of estrogen receptor ligands for the ERα and ERβ
Ligand Other names Relative binding affinities (RBA, %)a Absolute binding affinities (Ki, nM)a Action
ERα ERβ ERα ERβ
Estradiol E2; 17β-Estradiol 100 100 0.115 (0.04–0.24) 0.15 (0.10–2.08) Estrogen
Estrone E1; 17-Ketoestradiol 16.39 (0.7–60) 6.5 (1.36–52) 0.445 (0.3–1.01) 1.75 (0.35–9.24) Estrogen
Estriol E3; 16α-OH-17β-E2 12.65 (4.03–56) 26 (14.0–44.6) 0.45 (0.35–1.4) 0.7 (0.63–0.7) Estrogen
Estetrol E4; 15α,16α-Di-OH-17β-E2 4.0 3.0 4.9 19 Estrogen
Alfatradiol 17α-Estradiol 20.5 (7–80.1) 8.195 (2–42) 0.2–0.52 0.43–1.2 Metabolite
16-Epiestriol 16β-Hydroxy-17β-estradiol 7.795 (4.94–63) 50 ? ? Metabolite
17-Epiestriol 16α-Hydroxy-17α-estradiol 55.45 (29–103) 79–80 ? ? Metabolite
16,17-Epiestriol 16β-Hydroxy-17α-estradiol 1.0 13 ? ? Metabolite
2-Hydroxyestradiol 2-OH-E2 22 (7–81) 11–35 2.5 1.3 Metabolite
2-Methoxyestradiol 2-MeO-E2 0.0027–2.0 1.0 ? ? Metabolite
4-Hydroxyestradiol 4-OH-E2 13 (8–70) 7–56 1.0 1.9 Metabolite
4-Methoxyestradiol 4-MeO-E2 2.0 1.0 ? ? Metabolite
2-Hydroxyestrone 2-OH-E1 2.0–4.0 0.2–0.4 ? ? Metabolite
2-Methoxyestrone 2-MeO-E1 <0.001–<1 <1 ? ? Metabolite
4-Hydroxyestrone 4-OH-E1 1.0–2.0 1.0 ? ? Metabolite
4-Methoxyestrone 4-MeO-E1 <1 <1 ? ? Metabolite
16α-Hydroxyestrone 16α-OH-E1; 17-Ketoestriol 2.0–6.5 35 ? ? Metabolite
2-Hydroxyestriol 2-OH-E3 2.0 1.0 ? ? Metabolite
4-Methoxyestriol 4-MeO-E3 1.0 1.0 ? ? Metabolite
Estradiol sulfate E2S; Estradiol 3-sulfate <1 <1 ? ? Metabolite
Estradiol disulfate Estradiol 3,17β-disulfate 0.0004 ? ? ? Metabolite
Estradiol 3-glucuronide E2-3G 0.0079 ? ? ? Metabolite
Estradiol 17β-glucuronide E2-17G 0.0015 ? ? ? Metabolite
Estradiol 3-gluc. 17β-sulfate E2-3G-17S 0.0001 ? ? ? Metabolite
Estrone sulfate E1S; Estrone 3-sulfate <1 <1 >10 >10 Metabolite
Estradiol benzoate EB; Estradiol 3-benzoate 10 ? ? ? Estrogen
Estradiol 17β-benzoate E2-17B 11.3 32.6 ? ? Estrogen
Estrone methyl ether Estrone 3-methyl ether 0.145 ? ? ? Estrogen
ent-Estradiol 1-Estradiol 1.31–12.34 9.44–80.07 ? ? Estrogen
Equilin 7-Dehydroestrone 13 (4.0–28.9) 13.0–49 0.79 0.36 Estrogen
Equilenin 6,8-Didehydroestrone 2.0–15 7.0–20 0.64 0.62 Estrogen
17β-Dihydroequilin 7-Dehydro-17β-estradiol 7.9–113 7.9–108 0.09 0.17 Estrogen
17α-Dihydroequilin 7-Dehydro-17α-estradiol 18.6 (18–41) 14–32 0.24 0.57 Estrogen
17β-Dihydroequilenin 6,8-Didehydro-17β-estradiol 35–68 90–100 0.15 0.20 Estrogen
17α-Dihydroequilenin 6,8-Didehydro-17α-estradiol 20 49 0.50 0.37 Estrogen
Δ8-Estradiol 8,9-Dehydro-17β-estradiol 68 72 0.15 0.25 Estrogen
Δ8-Estrone 8,9-Dehydroestrone 19 32 0.52 0.57 Estrogen
Ethinylestradiol EE; 17α-Ethynyl-17β-E2 120.9 (68.8–480) 44.4 (2.0–144) 0.02–0.05 0.29–0.81 Estrogen
Mestranol EE 3-methyl ether ? 2.5 ? ? Estrogen
Moxestrol RU-2858; 11β-Methoxy-EE 35–43 5–20 0.5 2.6 Estrogen
Methylestradiol 17α-Methyl-17β-estradiol 70 44 ? ? Estrogen
Diethylstilbestrol DES; Stilbestrol 129.5 (89.1–468) 219.63 (61.2–295) 0.04 0.05 Estrogen
Hexestrol Dihydrodiethylstilbestrol 153.6 (31–302) 60–234 0.06 0.06 Estrogen
Dienestrol Dehydrostilbestrol 37 (20.4–223) 56–404 0.05 0.03 Estrogen
Benzestrol (B2) 114 ? ? ? Estrogen
Chlorotrianisene TACE 1.74 ? 15.30 ? Estrogen
Triphenylethylene TPE 0.074 ? ? ? Estrogen
Triphenylbromoethylene TPBE 2.69 ? ? ? Estrogen
Tamoxifen ICI-46,474 3 (0.1–47) 3.33 (0.28–6) 3.4–9.69 2.5 SERM
Afimoxifene 4-Hydroxytamoxifen; 4-OHT 100.1 (1.7–257) 10 (0.98–339) 2.3 (0.1–3.61) 0.04–4.8 SERM
Toremifene 4-Chlorotamoxifen; 4-CT ? ? 7.14–20.3 15.4 SERM
Clomifene MRL-41 25 (19.2–37.2) 12 0.9 1.2 SERM
Cyclofenil F-6066; Sexovid 151–152 243 ? ? SERM
Nafoxidine U-11,000A 30.9–44 16 0.3 0.8 SERM
Raloxifene 41.2 (7.8–69) 5.34 (0.54–16) 0.188–0.52 20.2 SERM
Arzoxifene LY-353,381 ? ? 0.179 ? SERM
Lasofoxifene CP-336,156 10.2–166 19.0 0.229 ? SERM
Ormeloxifene Centchroman ? ? 0.313 ? SERM
Levormeloxifene 6720-CDRI; NNC-460,020 1.55 1.88 ? ? SERM
Ospemifene Deaminohydroxytoremifene 0.82–2.63 0.59–1.22 ? ? SERM
Bazedoxifene ? ? 0.053 ? SERM
Etacstil GW-5638 4.30 11.5 ? ? SERM
ICI-164,384 63.5 (3.70–97.7) 166 0.2 0.08 Antiestrogen
Fulvestrant ICI-182,780 43.5 (9.4–325) 21.65 (2.05–40.5) 0.42 1.3 Antiestrogen
Propylpyrazoletriol PPT 49 (10.0–89.1) 0.12 0.40 92.8 ERα agonist
16α-LE2 16α-Lactone-17β-estradiol 14.6–57 0.089 0.27 131 ERα agonist
16α-Iodo-E2 16α-Iodo-17β-estradiol 30.2 2.30 ? ? ERα agonist
Methylpiperidinopyrazole MPP 11 0.05 ? ? ERα antagonist
Diarylpropionitrile DPN 0.12–0.25 6.6–18 32.4 1.7 ERβ agonist
8β-VE2 8β-Vinyl-17β-estradiol 0.35 22.0–83 12.9 0.50 ERβ agonist
Prinaberel ERB-041; WAY-202,041 0.27 67–72 ? ? ERβ agonist
ERB-196 WAY-202,196 ? 180 ? ? ERβ agonist
Erteberel SERBA-1; LY-500,307 ? ? 2.68 0.19 ERβ agonist
SERBA-2 ? ? 14.5 1.54 ERβ agonist
Coumestrol 9.225 (0.0117–94) 64.125 (0.41–185) 0.14–80.0 0.07–27.0 Xenoestrogen
Genistein 0.445 (0.0012–16) 33.42 (0.86–87) 2.6–126 0.3–12.8 Xenoestrogen
Equol 0.2–0.287 0.85 (0.10–2.85) ? ? Xenoestrogen
Daidzein 0.07 (0.0018–9.3) 0.7865 (0.04–17.1) 2.0 85.3 Xenoestrogen
Biochanin A 0.04 (0.022–0.15) 0.6225 (0.010–1.2) 174 8.9 Xenoestrogen
Kaempferol 0.07 (0.029–0.10) 2.2 (0.002–3.00) ? ? Xenoestrogen
Naringenin 0.0054 (<0.001–0.01) 0.15 (0.11–0.33) ? ? Xenoestrogen
8-Prenylnaringenin 8-PN 4.4 ? ? ? Xenoestrogen
Quercetin <0.001–0.01 0.002–0.040 ? ? Xenoestrogen
Ipriflavone <0.01 <0.01 ? ? Xenoestrogen
Miroestrol 0.39 ? ? ? Xenoestrogen
Deoxymiroestrol 2.0 ? ? ? Xenoestrogen
β-Sitosterol <0.001–0.0875 <0.001–0.016 ? ? Xenoestrogen
Resveratrol <0.001–0.0032 ? ? ? Xenoestrogen
α-Zearalenol 48 (13–52.5) ? ? ? Xenoestrogen
β-Zearalenol 0.6 (0.032–13) ? ? ? Xenoestrogen
Zeranol α-Zearalanol 48–111 ? ? ? Xenoestrogen
Taleranol β-Zearalanol 16 (13–17.8) 14 0.8 0.9 Xenoestrogen
Zearalenone ZEN 7.68 (2.04–28) 9.45 (2.43–31.5) ? ? Xenoestrogen
Zearalanone ZAN 0.51 ? ? ? Xenoestrogen
Bisphenol A BPA 0.0315 (0.008–1.0) 0.135 (0.002–4.23) 195 35 Xenoestrogen
Endosulfan EDS <0.001–<0.01 <0.01 ? ? Xenoestrogen
Kepone Chlordecone 0.0069–0.2 ? ? ? Xenoestrogen
o,p'-DDT 0.0073–0.4 ? ? ? Xenoestrogen
p,p'-DDT 0.03 ? ? ? Xenoestrogen
Methoxychlor p,p'-Dimethoxy-DDT 0.01 (<0.001–0.02) 0.01–0.13 ? ? Xenoestrogen
HPTE Hydroxychlor; p,p'-OH-DDT 1.2–1.7 ? ? ? Xenoestrogen
Testosterone T; 4-Androstenolone <0.0001–<0.01 <0.002–0.040 >5000 >5000 Androgen
Dihydrotestosterone DHT; 5α-Androstanolone 0.01 (<0.001–0.05) 0.0059–0.17 221–>5000 73–1688 Androgen
Nandrolone 19-Nortestosterone; 19-NT 0.01 0.23 765 53 Androgen
Dehydroepiandrosterone DHEA; Prasterone 0.038 (<0.001–0.04) 0.019–0.07 245–1053 163–515 Androgen
5-Androstenediol A5; Androstenediol 6 17 3.6 0.9 Androgen
4-Androstenediol 0.5 0.6 23 19 Androgen
4-Androstenedione A4; Androstenedione <0.01 <0.01 >10000 >10000 Androgen
3α-Androstanediol 3α-Adiol 0.07 0.3 260 48 Androgen
3β-Androstanediol 3β-Adiol 3 7 6 2 Androgen
Androstanedione 5α-Androstanedione <0.01 <0.01 >10000 >10000 Androgen
Etiocholanedione 5β-Androstanedione <0.01 <0.01 >10000 >10000 Androgen
Methyltestosterone 17α-Methyltestosterone <0.0001 ? ? ? Androgen
Ethinyl-3α-androstanediol 17α-Ethynyl-3α-adiol 4.0 <0.07 ? ? Estrogen
Ethinyl-3β-androstanediol 17α-Ethynyl-3β-adiol 50 5.6 ? ? Estrogen
Progesterone P4; 4-Pregnenedione <0.001–0.6 <0.001–0.010 ? ? Progestogen
Norethisterone NET; 17α-Ethynyl-19-NT 0.085 (0.0015–<0.1) 0.1 (0.01–0.3) 152 1084 Progestogen
Norethynodrel 5(10)-Norethisterone 0.5 (0.3–0.7) <0.1–0.22 14 53 Progestogen
Tibolone 7α-Methylnorethynodrel 0.5 (0.45–2.0) 0.2–0.076 ? ? Progestogen
Δ4-Tibolone 7α-Methylnorethisterone 0.069–<0.1 0.027–<0.1 ? ? Progestogen
3α-Hydroxytibolone 2.5 (1.06–5.0) 0.6–0.8 ? ? Progestogen
3β-Hydroxytibolone 1.6 (0.75–1.9) 0.070–0.1 ? ? Progestogen
Footnotes: a = (1) Binding affinity values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of in-vitro systems with labeled estradiol and human ERα and ERβ proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). Sources: See template page.

References

  1. ^ a b c Tan VY (2010). Characterization of the estrogenic activity of a synthetic adrenal steroid 17-α ethinyl androstenediol and its potential use in hormone replacement therapy (Ph.D. thesis). hdl:10356/45321.
  2. ^ Beyler AL, Clinton RO (June 1956). "Uterine growth stimulating and testicular growth suppressing activities of 17alpha-ethinylandrostane-3beta, 17beta-diol, its delta 5-analog and derivatives". Proc. Soc. Exp. Biol. Med. 92 (2): 404–8. doi:10.3181/00379727-92-22493. PMID 13350363. S2CID 87469965.
  3. ^ Masson G, Selye H (1945). "Additional steroids with luteoid activity". Journal of Pharmacology and Experimental Therapeutics. 84 (1): 46–52. JSTOR 1671439.
  4. ^ Overbeek GA (1948). "Luteoid activity of ethinyl-androstenediol". Acta Brevia Neerl Physiol Pharmacol Microbiol e A. 15 (5–7): 68. PMID 18873577.
  5. ^ Mardones E, Iglesias R, Lipschutz A (February 1956). "The antiluteinizing potency of five derivatives of progesterone". Endocrinology. 58 (2): 212–9. doi:10.1210/endo-58-2-212. PMID 13285465.
  6. ^ Neumann F (1968). "Chemische Konstitution und pharmakologische Wirkung". Die Gestagene. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology. Springer. pp. 680–1025. doi:10.1007/978-3-642-99941-3_6. ISBN 978-3-642-99942-0.
  7. ^ Stavely HE (1939). "Preparation of a Pregnane Compound from Dehydroandrosterone". Journal of the American Chemical Society. 61 (1): 79–80. doi:10.1021/ja01870a023. ISSN 0002-7863.
  8. ^ Stavely HE (1940). "The Preparation of Δ5-Pregnenediol-3,17-one-20 from Δ5-17-Ethynyl-androstenediol-3,17". Journal of the American Chemical Society. 62 (3): 489–491. doi:10.1021/ja01860a007. ISSN 0002-7863.
  9. ^ a b c Emmens CW (22 October 2013). Hormone Assay. Elsevier Science. pp. 422–. ISBN 978-1-4832-7286-3.
  10. ^ Sneader W (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 200–. ISBN 978-0-471-89979-2.
  11. ^ Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J (February 2012). "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs. 30 (1): 59–78. doi:10.1007/s10637-010-9517-0. PMID 20814732. S2CID 24785562.
  12. ^ Shipley EG (1962). "Anti-gonadotropic steroids, inhibition of ovulation and mating". In Dorfman RI (ed.). Bioassay. Elsevier. pp. 179–274. ISBN 978-1-4832-7276-4.
  13. ^ Boccabella A, Bakritges C (January 1956). "Effects of ethandrostate on pituitary and sex organs of rats". Anatomical Record. 124 (2): 260.
  14. ^ Clinton R, Neumann H, Laskowski S, Christiansen R (1957). "Esters of 17α-Ethinyl-androstane-3β,17β-diol and 17 α-Ethinylandrost-5-ene-3β, 17β-diol". The Journal of Organic Chemistry. 22 (4): 473–475. doi:10.1021/jo01355a627. ISSN 0022-3263.
  15. ^ Olson KB, Frawley TF, Stein AA, Shields D (1958). "Ethandrostate: endocrine effects and studies in treatment of cancer". Cancer. 11 (3): 537–45. doi:10.1002/1097-0142(195805/06)11:3<537::aid-cncr2820110313>3.0.co;2-w. PMID 13523561. S2CID 738607.



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У этого термина существуют и другие значения, см. 21-я дивизия. 21-я парашютная дивизия 21. Fallschirm-Jäger-Division Годы существования апрель - май 1945 Страна нацистская Германия Подчинение Люфтваффе Дислокация Западный фронт Войны Вторая мировая война Участие в бои в Нидерландах 1945 К�...

 

 

Decomposition of an integer as a sum of positive integers This article is about partitioning an integer. For grouping elements of a set, see Partition of a set. For the partition calculus of sets, see Infinitary combinatorics. For the problem of partitioning a multiset of integers so that each part has the same sum, see Partition problem. Young diagrams associated to the partitions of the positive integers 1 through 8. They are arranged so that images under the reflection about the main diago...

French botanist Pierre Magnol Pierre Magnol (8 June 1638 – 21 May 1715)[1][2] was a French botanist. He was born in the city of Montpellier, where he lived and worked for most of his life. He became Professor of Botany and Director of the Royal Botanic Garden of Montpellier and held a seat in the Académie Royale des Sciences de Paris for a short while. He was one of the innovators who devised the botanical scheme of classification. He was the first to publish the concept of...

 

 

LanuviumGéographiePays  ItalieRégion LatiumVille métropolitaine ville métropolitaine de Rome CapitaleCommune LanuvioCoordonnées 41° 40′ 29″ N, 12° 41′ 51″ EHistoireRemplacé par Lanuviomodifier - modifier le code - modifier Wikidata Lanuvium est une cité antique latine du Latium, dans les monts Albains, en Italie centrale, aujourd’hui connue sous le nom de Lanuvio. Histoire Fondation légendaire Des vestiges de l’âge du fer montrent que ...

 

 

Ballon d'or 1962 Josef Masopust en 1962Généralités Sport Football Organisateur(s) France Football Édition 7e Catégorie Trophée européen Date 1962 Participants Joueurs européens évoluant en Europe Site web officiel Site officiel Palmarès Vainqueur Josef Masopust (1) Deuxième Eusébio Troisième Karl-Heinz Schnellinger Navigation Édition précédente Édition suivante modifier Le Ballon d'or 1962 récompensant le meilleur footballeur européen évoluant en Europe a été attribué ...

Hebrew song written by Naomi Shemer Menorah(מְנוֹרָה) Flag of Israel Jewish andIsraeli music Religious Contemporary Piyyut Zemirot Nigun Pizmonim Baqashot Secular Klezmer Sephardic Mizrahi Mainstream and jazz Classical Jewish art music Israel Hatikvah Jerusalem of Gold We Are Both from the Same Village Dance Israeli folk dancing Ballet Horah Yemenite dancing Music for holidays Shabbat Hanukkah Blessings Oh Chanukah Dreidel song Al Hanisim Mi Y'malel Ner Li Passover (Haggadah) Ma Nisht...

 

 

Chief deity of Roman state religion Jove redirects here. For other uses, see Jove (disambiguation). JupiterKing of the Gods God of the sky and diurnal thunderMember of the Archaic Triad, Capitoline Triad and the Dii ConsentesA marble statue of JupiterOther namesJoveVenerated inImperial cult of ancient RomePolytheistic religionAbodeThe heavensPlanetJupiter[1]SymbolLightning bolt, eagle, oak treeDayThursday (dies Jovis)GenealogyParentsSaturn and Ops[2][3]SiblingsVesta, C...