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Abandoned drugs
Ethinylandrostenediol
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    Ethinylandrostenediol

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    Ethinylandrostenediol
    Ethinylandrostenediol.svg
    Clinical data
    Other names SKF-2856; 17α-Ethynyl-5-androstenediol; 17α-Ethynylandrost-5-ene-3β,17-diol; 17α-Pregn-5-en-20-yne-3β,17-diol; NSC-17098
    Drug class Estrogen; 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
    Formula C21H30O2
    Molar mass 314.469 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. It is the C17α ethynyl derivative of the androgen precursor and prohormone 5-androstenediol.

    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. Ethinylandrostenediol is orally active similarly to ethisterone and shows about half its progestogenic potency. Ethinylandrostenediol was an intermediate in the initial synthesis of ethisterone.

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

    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.

    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.




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