17α-Ethynyl-3α-androstanediol (developmental code names HE-3235 , Apoptone ), also known as 17α-ethynyl-5α-androstane-3α,17β-diol , is a synthetic androstane steroid and a 17α-substituted derivative of 3α-androstanediol which was never marketed.[1] [2] [3] prostate cancer but was discontinued.[1] [2] [3]
17α-Ethynyl-3α-androstanediol Clinical data Other names Ethynylandrostanediol; HE3235; Apoptone; 17α-Ethynyl-5α-androstanediol; 17α-Ethynyl-5α-androstane-3α,17β-diol; 5α-Pregn-20-yne-3α,17α-diol Routes of By mouth Drug class Estrogen Identifiers (3R ,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 ChemSpider UNII CompTox Dashboard (EPA ) Chemical and physical data Formula C 21 H 32 O 2 Molar mass −1 3D model (JSmol ) C[C@]12CC[C@H](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-JRRMKBMNSA-N
17α-Ethynyl-3α-androstanediol itself shows very low affinity for steroid receptors , including the AR Tooltip androgen receptor , ERα Tooltip estrogen receptor alpha , ERβ Tooltip estrogen receptor beta , PR Tooltip progesterone receptor , and GR Tooltip glucocorticoid receptor , and its mechanism of action is not well-characterized.[1] [4] 5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone), a ligand of several steroid hormone receptors , and 17α-ethynyl-3β-androstanediol , an estrogen , as active metabolites .[1] [5] biological activity of 17α-ethynyl-3α-androstanediol, with 17α-ethynyl-3α-androstanediol potentially serving as a prodrug .[1] [5]
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-3α-androstanediol include 17α-ethynyl-3β-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 c d e Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J (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. ^ a b Trauger R, Corey E, Bell D, White S, Garsd A, Stickney D, Reading C, Frincke J (2009). "Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235)". Br. J. Cancer . 100 (7): 1068–72. doi :10.1038/sj.bjc.6604987. PMC 2669987 . PMID 19337256. ^ a b [1] [permanent dead link ^ Koreckij TD, Trauger RJ, Montgomery RB, Pitts TE, Coleman I, Nguyen H, Reading CL, Nelson PS, Vessella RL, Corey E (2009). "HE3235 inhibits growth of castration-resistant prostate cancer". Neoplasia . 11 (11): 1216–25. doi :10.1593/neo.09960. PMC 2767223 . PMID 19881957. ^ 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". Proc. Soc. Exp. Biol. Med . 92 (2): 404–8. doi :10.3181/00379727-92-22493. PMID 13350363. S2CID 87469965.
17α, ethynyl, androstanediol, developmental, code, names, 3235, apoptone, also, known, 17α, ethynyl, androstane, 17β, diol, synthetic, androstane, steroid, 17α, substituted, derivative, androstanediol, which, never, marketed, under, development, treatment, pro. 17a Ethynyl 3a androstanediol developmental code names HE 3235 Apoptone also known as 17a ethynyl 5a androstane 3a 17b diol is a synthetic androstane steroid and a 17a substituted derivative of 3a androstanediol which was never marketed 1 2 3 It was under development for the treatment of prostate cancer but was discontinued 1 2 3 17a Ethynyl 3a androstanediolClinical dataOther namesEthynylandrostanediol HE3235 Apoptone 17a Ethynyl 5a androstanediol 17a Ethynyl 5a androstane 3a 17b diol 5a Pregn 20 yne 3a 17a diolRoutes ofadministrationBy mouthDrug classEstrogenIdentifiersIUPAC name 3R 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 Number183387 50 0PubChem CID42611099ChemSpider32698509UNII891O182ZP5CompTox Dashboard EPA DTXSID70171418Chemical and physical dataFormulaC 21H 32O 2Molar mass316 485 g mol 13D model JSmol Interactive imageSMILES C C 12CC C H 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 JRRMKBMNSA N 17a Ethynyl 3a androstanediol itself shows very low affinity for steroid receptors including the ARTooltip androgen receptor ERaTooltip estrogen receptor alpha ERbTooltip estrogen receptor beta PRTooltip progesterone receptor and GRTooltip glucocorticoid receptor and its mechanism of action is not well characterized 1 4 It produces 5a dihydroethisterone 5a dihydro 17a ethynyltestosterone a ligand of several steroid hormone receptors and 17a ethynyl 3b androstanediol an estrogen as active metabolites 1 5 These metabolites may contribute importantly to the biological activity of 17a ethynyl 3a androstanediol with 17a ethynyl 3a androstanediol potentially serving as a prodrug 1 5 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 Action ERa ERb ERa ERb Estradiol E2 17b 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 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 Estrogen Estetrol E4 15a 16a Di OH 17b E2 4 0 3 0 4 9 19 Estrogen Alfatradiol 17a Estradiol 20 5 7 80 1 8 195 2 42 0 2 0 52 0 43 1 2 Metabolite 16 Epiestriol 16b Hydroxy 17b estradiol 7 795 4 94 63 50 Metabolite 17 Epiestriol 16a Hydroxy 17a estradiol 55 45 29 103 79 80 Metabolite 16 17 Epiestriol 16b Hydroxy 17a 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 lt 0 001 lt 1 lt 1 Metabolite 4 Hydroxyestrone 4 OH E1 1 0 2 0 1 0 Metabolite 4 Methoxyestrone 4 MeO E1 lt 1 lt 1 Metabolite 16a Hydroxyestrone 16a 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 lt 1 lt 1 Metabolite Estradiol disulfate Estradiol 3 17b disulfate 0 0004 Metabolite Estradiol 3 glucuronide E2 3G 0 0079 Metabolite Estradiol 17b glucuronide E2 17G 0 0015 Metabolite Estradiol 3 gluc 17b sulfate E2 3G 17S 0 0001 Metabolite Estrone sulfate E1S Estrone 3 sulfate lt 1 lt 1 gt 10 gt 10 Metabolite Estradiol benzoate EB Estradiol 3 benzoate 10 Estrogen Estradiol 17b 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 17b Dihydroequilin 7 Dehydro 17b estradiol 7 9 113 7 9 108 0 09 0 17 Estrogen 17a Dihydroequilin 7 Dehydro 17a estradiol 18 6 18 41 14 32 0 24 0 57 Estrogen 17b Dihydroequilenin 6 8 Didehydro 17b estradiol 35 68 90 100 0 15 0 20 Estrogen 17a Dihydroequilenin 6 8 Didehydro 17a estradiol 20 49 0 50 0 37 Estrogen D8 Estradiol 8 9 Dehydro 17b estradiol 68 72 0 15 0 25 Estrogen D8 Estrone 8 9 Dehydroestrone 19 32 0 52 0 57 Estrogen Ethinylestradiol EE 17a Ethynyl 17b 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 11b Methoxy EE 35 43 5 20 0 5 2 6 Estrogen Methylestradiol 17a Methyl 17b 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 ERa agonist 16a LE2 16a Lactone 17b estradiol 14 6 57 0 089 0 27 131 ERa agonist 16a Iodo E2 16a Iodo 17b estradiol 30 2 2 30 ERa agonist Methylpiperidinopyrazole MPP 11 0 05 ERa antagonist Diarylpropionitrile DPN 0 12 0 25 6 6 18 32 4 1 7 ERb agonist 8b VE2 8b Vinyl 17b estradiol 0 35 22 0 83 12 9 0 50 ERb agonist Prinaberel ERB 041 WAY 202 041 0 27 67 72 ERb agonist ERB 196 WAY 202 196 180 ERb agonist Erteberel SERBA 1 LY 500 307 2 68 0 19 ERb agonist SERBA 2 14 5 1 54 ERb 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 lt 0 001 0 01 0 15 0 11 0 33 Xenoestrogen 8 Prenylnaringenin 8 PN 4 4 Xenoestrogen Quercetin lt 0 001 0 01 0 002 0 040 Xenoestrogen Ipriflavone lt 0 01 lt 0 01 Xenoestrogen Miroestrol 0 39 Xenoestrogen Deoxymiroestrol 2 0 Xenoestrogen b Sitosterol lt 0 001 0 0875 lt 0 001 0 016 Xenoestrogen Resveratrol lt 0 001 0 0032 Xenoestrogen a Zearalenol 48 13 52 5 Xenoestrogen b Zearalenol 0 6 0 032 13 Xenoestrogen Zeranol a Zearalanol 48 111 Xenoestrogen Taleranol b 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 lt 0 001 lt 0 01 lt 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 lt 0 001 0 02 0 01 0 13 Xenoestrogen HPTE Hydroxychlor p p OH DDT 1 2 1 7 Xenoestrogen Testosterone T 4 Androstenolone lt 0 0001 lt 0 01 lt 0 002 0 040 gt 5000 gt 5000 Androgen Dihydrotestosterone DHT 5a Androstanolone 0 01 lt 0 001 0 05 0 0059 0 17 221 gt 5000 73 1688 Androgen Nandrolone 19 Nortestosterone 19 NT 0 01 0 23 765 53 Androgen Dehydroepiandrosterone DHEA Prasterone 0 038 lt 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 lt 0 01 lt 0 01 gt 10000 gt 10000 Androgen 3a Androstanediol 3a Adiol 0 07 0 3 260 48 Androgen 3b Androstanediol 3b Adiol 3 7 6 2 Androgen Androstanedione 5a Androstanedione lt 0 01 lt 0 01 gt 10000 gt 10000 Androgen Etiocholanedione 5b Androstanedione lt 0 01 lt 0 01 gt 10000 gt 10000 Androgen Methyltestosterone 17a Methyltestosterone lt 0 0001 Androgen Ethinyl 3a androstanediol 17a Ethynyl 3a adiol 4 0 lt 0 07 Estrogen Ethinyl 3b androstanediol 17a Ethynyl 3b adiol 50 5 6 Estrogen Progesterone P4 4 Pregnenedione lt 0 001 0 6 lt 0 001 0 010 Progestogen Norethisterone NET 17a Ethynyl 19 NT 0 085 0 0015 lt 0 1 0 1 0 01 0 3 152 1084 Progestogen Norethynodrel 5 10 Norethisterone 0 5 0 3 0 7 lt 0 1 0 22 14 53 Progestogen Tibolone 7a Methylnorethynodrel 0 5 0 45 2 0 0 2 0 076 Progestogen D4 Tibolone 7a Methylnorethisterone 0 069 lt 0 1 0 027 lt 0 1 Progestogen 3a Hydroxytibolone 2 5 1 06 5 0 0 6 0 8 Progestogen 3b 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 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 3a androstanediol include 17a ethynyl 3b 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 c d e Ahlem C Kennedy M Page T Bell D Delorme E Villegas S Reading C White S Stickney D Frincke J 2012 17a alkynyl 3a 17b 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 a b Trauger R Corey E Bell D White S Garsd A Stickney D Reading C Frincke J 2009 Inhibition of androstenediol dependent LNCaP tumour growth by 17alpha ethynyl 5alpha androstane 3alpha 17beta diol HE3235 Br J Cancer 100 7 1068 72 doi 10 1038 sj bjc 6604987 PMC 2669987 PMID 19337256 a b 1 permanent dead link Koreckij TD Trauger RJ Montgomery RB Pitts TE Coleman I Nguyen H Reading CL Nelson PS Vessella RL Corey E 2009 HE3235 inhibits growth of castration resistant prostate cancer Neoplasia 11 11 1216 25 doi 10 1593 neo 09960 PMC 2767223 PMID 19881957 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 Proc Soc Exp Biol Med 92 2 404 8 doi 10 3181 00379727 92 22493 PMID 13350363 S2CID 87469965 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 3a androstanediol amp oldid 1205936303, 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.