17α-Ethynyl-3β-androstanediol (developmental code HE-3539 ; also known as 17α-ethynyl-5α-androstane-3β,17β-diol ) is a synthetic estrogen and a 17α-substituted derivative of 3β-androstanediol which was never marketed.[1] [2]
17α-Ethynyl-3β-androstanediol Clinical data Other names HE-3539; HE3539; Ethinylandrostanediol; 17α-Ethynyl-5α-androstane-3β,17β-diol; 5α,17α-Pregn-20-yne-3β,17-diol Routes of By mouth Drug class Estrogen Identifiers (5S ,8R ,9S ,10S ,13S ,14S ,17R )-17-ethynyl-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a ]phenanthrene-3,17-diol
CAS Number PubChem CID Chemical and physical data Formula C 21 H 32 O 2 Molar mass −1 3D model (JSmol ) C[C@]12CCC(C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O
InChI=1S/C21H32O2/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/h1,14-18,22-23H,5-13H2,2-3H3/t14-,15?,16+,17-,18-,19-,20-,21-/m0/s1
Key:CKAXZOYFIHQCBN-KVECEQEYSA-N
17α-Ethynyl-3β-androstanediol shows high affinity for the estrogen receptors in vitro IC50 Tooltip Half-maximal inhibitory concentration values of 16 nM for ERα and 126 nM for ERβ relative to values of 8 nM at ERα and 7 nM at ERβ for estradiol ), and activates the estrogen receptors in vitro (EC50 Tooltip Half-maximal effective concentration value of 0.9 nM relative to 0.002 nM for estradiol).[2] androgen receptor in vitro (IC50 = 277 nM relative to 15 nM for dihydrotestosterone ), but doesn't appear to activate the receptor.[2] 17α-ethynyl-3α-androstanediol and 5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone) as active metabolites in vivo [2] in-vitro estrogenic activity, 17α-ethynyl-3β-androstanediol produces estrogenic effects like uterotrophy and testicular atrophy in animals.[1]
Esters of 17α-ethynyl-3β-androstanediol have been developed and studied.[3]
17α-Ethynyl-3β-androstanediol is a positional isomer of 17α-ethynyl-3α-androstanediol, and is a metabolite of this compound in vivo metabolic inversion of the position of the C3 hydroxyl group .[2] biological activity of 17α-ethynyl-3α-androstanediol.[2]
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 -Estradiol1-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-DDT0.01 (<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 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.
Analogues of 17α-ethynyl-3β-androstanediol include 17α-ethynyl-3α-androstanediol , ethinylandrostenediol (17α-ethynyl-5-androstenediol), ethandrostate (17α-ethynyl-5-androstenediol 3β-cyclohexanepropionate), ethinylestradiol (17α-ethynylestradiol), ethisterone (17α-ethynyltestosterone), and 5α-dihydroethisterone (17α-ethynyldihydrotestosterone).
References edit ^ a b 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". Proceedings of the Society for Experimental Biology and Medicine . 92 (2): 404–408. doi :10.3181/00379727-92-22493. PMID 13350363. S2CID 87469965. ^ a b c d e f Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, et al. (February 2012). "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Investigational New Drugs . 30 (1): 59–78. doi :10.1007/s10637-010-9517-0. PMID 20814732. S2CID 24785562. ^ Clinton R, Neumann H, Laskowski S, Christiansen R (1957). "Notes - 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.
17α, ethynyl, androstanediol, developmental, code, 3539, also, known, 17α, ethynyl, androstane, 17β, diol, synthetic, estrogen, 17α, substituted, derivative, androstanediol, which, never, marketed, clinical, dataother, nameshe, 3539, he3539, ethinylandrostaned. 17a Ethynyl 3b androstanediol developmental code HE 3539 also known as 17a ethynyl 5a androstane 3b 17b diol is a synthetic estrogen and a 17a substituted derivative of 3b androstanediol which was never marketed 1 2 17a Ethynyl 3b androstanediolClinical dataOther namesHE 3539 HE3539 Ethinylandrostanediol 17a Ethynyl 5a androstane 3b 17b diol 5a 17a Pregn 20 yne 3b 17 diolRoutes ofadministrationBy mouthDrug classEstrogenIdentifiersIUPAC name 5S 8R 9S 10S 13S 14S 17R 17 ethynyl 10 13 dimethyl 1 2 3 4 5 6 7 8 9 11 12 14 15 16 tetradecahydrocyclopenta a phenanthrene 3 17 diolCAS Number13611 96 6PubChem CID45042186Chemical and physical dataFormulaC 21H 32O 2Molar mass316 485 g mol 13D model JSmol Interactive imageSMILES C C 12CCC C C H 1CC C H 3 C H 2CC C 4 C H 3CC C 4 C C O C OInChI InChI 1S C21H32O2 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 14 18 22 23H 5 13H2 2 3H3 t14 15 16 17 18 19 20 21 m0 s1Key CKAXZOYFIHQCBN KVECEQEYSA N17a Ethynyl 3b androstanediol shows high affinity for the estrogen receptors in vitro IC50Tooltip Half maximal inhibitory concentration values of 16 nM for ERa and 126 nM for ERb relative to values of 8 nM at ERa and 7 nM at ERb for estradiol and activates the estrogen receptors in vitro EC50Tooltip Half maximal effective concentration value of 0 9 nM relative to 0 002 nM for estradiol 2 It also has weak affinity for the androgen receptor in vitro IC50 277 nM relative to 15 nM for dihydrotestosterone but doesn t appear to activate the receptor 2 17a Ethynyl 3b androstanediol may produce 17a ethynyl 3a androstanediol and 5a dihydroethisterone 5a dihydro 17a ethynyltestosterone as active metabolites in vivo 2 In accordance with its in vitro estrogenic activity 17a ethynyl 3b androstanediol produces estrogenic effects like uterotrophy and testicular atrophy in animals 1 Esters of 17a ethynyl 3b androstanediol have been developed and studied 3 17a Ethynyl 3b androstanediol is a positional isomer of 17a ethynyl 3a androstanediol and is a metabolite of this compound in vivo via metabolic inversion of the position of the C3 hydroxyl group 2 It may be involved in the biological activity of 17a ethynyl 3a androstanediol 2 vte Affinities of estrogen receptor ligands for the ERa and ERb Ligand Other names Relative binding affinities RBA a Absolute binding affinities Ki nM a ActionERa ERb ERa ERbEstradiol E2 17b Estradiol 100 100 0 115 0 04 0 24 0 15 0 10 2 08 EstrogenEstrone 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 EstrogenEstriol E3 16a OH 17b E2 12 65 4 03 56 26 14 0 44 6 0 45 0 35 1 4 0 7 0 63 0 7 EstrogenEstetrol E4 15a 16a Di OH 17b E2 4 0 3 0 4 9 19 EstrogenAlfatradiol 17a Estradiol 20 5 7 80 1 8 195 2 42 0 2 0 52 0 43 1 2 Metabolite16 Epiestriol 16b Hydroxy 17b estradiol 7 795 4 94 63 50 Metabolite17 Epiestriol 16a Hydroxy 17a estradiol 55 45 29 103 79 80 Metabolite16 17 Epiestriol 16b Hydroxy 17a estradiol 1 0 13 Metabolite2 Hydroxyestradiol 2 OH E2 22 7 81 11 35 2 5 1 3 Metabolite2 Methoxyestradiol 2 MeO E2 0 0027 2 0 1 0 Metabolite4 Hydroxyestradiol 4 OH E2 13 8 70 7 56 1 0 1 9 Metabolite4 Methoxyestradiol 4 MeO E2 2 0 1 0 Metabolite2 Hydroxyestrone 2 OH E1 2 0 4 0 0 2 0 4 Metabolite2 Methoxyestrone 2 MeO E1 lt 0 001 lt 1 lt 1 Metabolite4 Hydroxyestrone 4 OH E1 1 0 2 0 1 0 Metabolite4 Methoxyestrone 4 MeO E1 lt 1 lt 1 Metabolite16a Hydroxyestrone 16a OH E1 17 Ketoestriol 2 0 6 5 35 Metabolite2 Hydroxyestriol 2 OH E3 2 0 1 0 Metabolite4 Methoxyestriol 4 MeO E3 1 0 1 0 MetaboliteEstradiol sulfate E2S Estradiol 3 sulfate lt 1 lt 1 MetaboliteEstradiol disulfate Estradiol 3 17b disulfate 0 0004 MetaboliteEstradiol 3 glucuronide E2 3G 0 0079 MetaboliteEstradiol 17b glucuronide E2 17G 0 0015 MetaboliteEstradiol 3 gluc 17b sulfate E2 3G 17S 0 0001 MetaboliteEstrone sulfate E1S Estrone 3 sulfate lt 1 lt 1 gt 10 gt 10 MetaboliteEstradiol benzoate EB Estradiol 3 benzoate 10 EstrogenEstradiol 17b benzoate E2 17B 11 3 32 6 EstrogenEstrone methyl ether Estrone 3 methyl ether 0 145 Estrogenent Estradiol 1 Estradiol 1 31 12 34 9 44 80 07 EstrogenEquilin 7 Dehydroestrone 13 4 0 28 9 13 0 49 0 79 0 36 EstrogenEquilenin 6 8 Didehydroestrone 2 0 15 7 0 20 0 64 0 62 Estrogen17b Dihydroequilin 7 Dehydro 17b estradiol 7 9 113 7 9 108 0 09 0 17 Estrogen17a Dihydroequilin 7 Dehydro 17a estradiol 18 6 18 41 14 32 0 24 0 57 Estrogen17b Dihydroequilenin 6 8 Didehydro 17b estradiol 35 68 90 100 0 15 0 20 Estrogen17a Dihydroequilenin 6 8 Didehydro 17a estradiol 20 49 0 50 0 37 EstrogenD8 Estradiol 8 9 Dehydro 17b estradiol 68 72 0 15 0 25 EstrogenD8 Estrone 8 9 Dehydroestrone 19 32 0 52 0 57 EstrogenEthinylestradiol EE 17a Ethynyl 17b E2 120 9 68 8 480 44 4 2 0 144 0 02 0 05 0 29 0 81 EstrogenMestranol EE 3 methyl ether 2 5 EstrogenMoxestrol RU 2858 11b Methoxy EE 35 43 5 20 0 5 2 6 EstrogenMethylestradiol 17a Methyl 17b estradiol 70 44 EstrogenDiethylstilbestrol DES Stilbestrol 129 5 89 1 468 219 63 61 2 295 0 04 0 05 EstrogenHexestrol Dihydrodiethylstilbestrol 153 6 31 302 60 234 0 06 0 06 EstrogenDienestrol Dehydrostilbestrol 37 20 4 223 56 404 0 05 0 03 EstrogenBenzestrol B2 114 EstrogenChlorotrianisene TACE 1 74 15 30 EstrogenTriphenylethylene TPE 0 074 EstrogenTriphenylbromoethylene TPBE 2 69 EstrogenTamoxifen ICI 46 474 3 0 1 47 3 33 0 28 6 3 4 9 69 2 5 SERMAfimoxifene 4 Hydroxytamoxifen 4 OHT 100 1 1 7 257 10 0 98 339 2 3 0 1 3 61 0 04 4 8 SERMToremifene 4 Chlorotamoxifen 4 CT 7 14 20 3 15 4 SERMClomifene MRL 41 25 19 2 37 2 12 0 9 1 2 SERMCyclofenil F 6066 Sexovid 151 152 243 SERMNafoxidine U 11 000A 30 9 44 16 0 3 0 8 SERMRaloxifene 41 2 7 8 69 5 34 0 54 16 0 188 0 52 20 2 SERMArzoxifene LY 353 381 0 179 SERMLasofoxifene CP 336 156 10 2 166 19 0 0 229 SERMOrmeloxifene Centchroman 0 313 SERMLevormeloxifene 6720 CDRI NNC 460 020 1 55 1 88 SERMOspemifene Deaminohydroxytoremifene 0 82 2 63 0 59 1 22 SERMBazedoxifene 0 053 SERMEtacstil GW 5638 4 30 11 5 SERMICI 164 384 63 5 3 70 97 7 166 0 2 0 08 AntiestrogenFulvestrant ICI 182 780 43 5 9 4 325 21 65 2 05 40 5 0 42 1 3 AntiestrogenPropylpyrazoletriol PPT 49 10 0 89 1 0 12 0 40 92 8 ERa agonist16a LE2 16a Lactone 17b estradiol 14 6 57 0 089 0 27 131 ERa agonist16a Iodo E2 16a Iodo 17b estradiol 30 2 2 30 ERa agonistMethylpiperidinopyrazole MPP 11 0 05 ERa antagonistDiarylpropionitrile DPN 0 12 0 25 6 6 18 32 4 1 7 ERb agonist8b VE2 8b Vinyl 17b estradiol 0 35 22 0 83 12 9 0 50 ERb agonistPrinaberel ERB 041 WAY 202 041 0 27 67 72 ERb agonistERB 196 WAY 202 196 180 ERb agonistErteberel SERBA 1 LY 500 307 2 68 0 19 ERb agonistSERBA 2 14 5 1 54 ERb agonistCoumestrol 9 225 0 0117 94 64 125 0 41 185 0 14 80 0 0 07 27 0 XenoestrogenGenistein 0 445 0 0012 16 33 42 0 86 87 2 6 126 0 3 12 8 XenoestrogenEquol 0 2 0 287 0 85 0 10 2 85 XenoestrogenDaidzein 0 07 0 0018 9 3 0 7865 0 04 17 1 2 0 85 3 XenoestrogenBiochanin A 0 04 0 022 0 15 0 6225 0 010 1 2 174 8 9 XenoestrogenKaempferol 0 07 0 029 0 10 2 2 0 002 3 00 XenoestrogenNaringenin 0 0054 lt 0 001 0 01 0 15 0 11 0 33 Xenoestrogen8 Prenylnaringenin 8 PN 4 4 XenoestrogenQuercetin lt 0 001 0 01 0 002 0 040 XenoestrogenIpriflavone lt 0 01 lt 0 01 XenoestrogenMiroestrol 0 39 XenoestrogenDeoxymiroestrol 2 0 Xenoestrogenb Sitosterol lt 0 001 0 0875 lt 0 001 0 016 XenoestrogenResveratrol lt 0 001 0 0032 Xenoestrogena Zearalenol 48 13 52 5 Xenoestrogenb Zearalenol 0 6 0 032 13 XenoestrogenZeranol a Zearalanol 48 111 XenoestrogenTaleranol b Zearalanol 16 13 17 8 14 0 8 0 9 XenoestrogenZearalenone ZEN 7 68 2 04 28 9 45 2 43 31 5 XenoestrogenZearalanone ZAN 0 51 XenoestrogenBisphenol A BPA 0 0315 0 008 1 0 0 135 0 002 4 23 195 35 XenoestrogenEndosulfan EDS lt 0 001 lt 0 01 lt 0 01 XenoestrogenKepone Chlordecone 0 0069 0 2 Xenoestrogeno p DDT 0 0073 0 4 Xenoestrogenp p DDT 0 03 XenoestrogenMethoxychlor p p Dimethoxy DDT 0 01 lt 0 001 0 02 0 01 0 13 XenoestrogenHPTE Hydroxychlor p p OH DDT 1 2 1 7 XenoestrogenTestosterone T 4 Androstenolone lt 0 0001 lt 0 01 lt 0 002 0 040 gt 5000 gt 5000 AndrogenDihydrotestosterone DHT 5a Androstanolone 0 01 lt 0 001 0 05 0 0059 0 17 221 gt 5000 73 1688 AndrogenNandrolone 19 Nortestosterone 19 NT 0 01 0 23 765 53 AndrogenDehydroepiandrosterone DHEA Prasterone 0 038 lt 0 001 0 04 0 019 0 07 245 1053 163 515 Androgen5 Androstenediol A5 Androstenediol 6 17 3 6 0 9 Androgen4 Androstenediol 0 5 0 6 23 19 Androgen4 Androstenedione A4 Androstenedione lt 0 01 lt 0 01 gt 10000 gt 10000 Androgen3a Androstanediol 3a Adiol 0 07 0 3 260 48 Androgen3b Androstanediol 3b Adiol 3 7 6 2 AndrogenAndrostanedione 5a Androstanedione lt 0 01 lt 0 01 gt 10000 gt 10000 AndrogenEtiocholanedione 5b Androstanedione lt 0 01 lt 0 01 gt 10000 gt 10000 AndrogenMethyltestosterone 17a Methyltestosterone lt 0 0001 AndrogenEthinyl 3a androstanediol 17a Ethynyl 3a adiol 4 0 lt 0 07 EstrogenEthinyl 3b androstanediol 17a Ethynyl 3b adiol 50 5 6 EstrogenProgesterone P4 4 Pregnenedione lt 0 001 0 6 lt 0 001 0 010 ProgestogenNorethisterone NET 17a Ethynyl 19 NT 0 085 0 0015 lt 0 1 0 1 0 01 0 3 152 1084 ProgestogenNorethynodrel 5 10 Norethisterone 0 5 0 3 0 7 lt 0 1 0 22 14 53 ProgestogenTibolone 7a Methylnorethynodrel 0 5 0 45 2 0 0 2 0 076 ProgestogenD4 Tibolone 7a Methylnorethisterone 0 069 lt 0 1 0 027 lt 0 1 Progestogen3a Hydroxytibolone 2 5 1 06 5 0 0 6 0 8 Progestogen3b Hydroxytibolone 1 6 0 75 1 9 0 070 0 1 ProgestogenFootnotes 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 ERa and ERb proteins except the ERb values from Kuiper et al 1997 which are rat ERb Sources See template page Analogues of 17a ethynyl 3b androstanediol include 17a ethynyl 3a androstanediol ethinylandrostenediol 17a ethynyl 5 androstenediol ethandrostate 17a ethynyl 5 androstenediol 3b cyclohexanepropionate ethinylestradiol 17a ethynylestradiol ethisterone 17a ethynyltestosterone and 5a dihydroethisterone 17a ethynyldihydrotestosterone References edit a b 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 Proceedings of the Society for Experimental Biology and Medicine 92 2 404 408 doi 10 3181 00379727 92 22493 PMID 13350363 S2CID 87469965 a b c d e f Ahlem C Kennedy M Page T Bell D Delorme E Villegas S et al February 2012 17a alkynyl 3a 17b androstanediol non clinical and clinical pharmacology pharmacokinetics and metabolism Investigational New Drugs 30 1 59 78 doi 10 1007 s10637 010 9517 0 PMID 20814732 S2CID 24785562 Clinton R Neumann H Laskowski S Christiansen R 1957 Notes Esters of 17a Ethinyl androstane 3b 17b diol and 17 a Ethinylandrost 5 ene 3b 17b diol The Journal of Organic Chemistry 22 4 473 475 doi 10 1021 jo01355a627 ISSN 0022 3263 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte nbsp This antineoplastic or immunomodulatory drug article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 17a Ethynyl 3b androstanediol amp oldid 1156516952, wikipedia, wiki , book, books, library,
article , read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.