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Nonsteroidal estrogen

Topic: Biology

 From HandWiki - Reading time: 11 min

Short description: Class of drugs
Nonsteroidal estrogen
Drug class
Diethylstilbestrol, one of the most well-known nonsteroidal estrogens.
Class identifiers
SynonymsNonsteroidal estrogen receptor agonists
ATC codeG03C
Biological targetEstrogen receptors (ERα, ERβ, mERs (e.g., GPER, others))
Chemical classNonsteroidal

A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure.[1] The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES).[1][2] Although nonsteroidal estrogens formerly had an important place in medicine, they have gradually fallen out of favor following the discovery of toxicities associated with high-dose DES starting in the early 1970s, and are now almost never used.[2][3][4] On the other hand, virtually all selective estrogen receptor modulators (SERMs) are nonsteroidal, with triphenylethylenes like tamoxifen and clomifene having been derived from DES,[5] and these drugs remain widely used in medicine for the treatment of breast cancer among other indications.[6] In addition to pharmaceutical drugs, many xenoestrogens, including phytoestrogens, mycoestrogens, and synthetic endocrine disruptors like bisphenol A, are nonsteroidal substances with estrogenic activity.[7]

Pharmacology

Nonsteroidal estrogens act as agonists of the estrogen receptors, ERα and ERβ.

v · d · e 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 Script error: The function "median" does not exist. (0.04–0.24) Script error: The function "median" does not exist. (0.10–2.08) Estrogen
Estrone E1; 17-Ketoestradiol Script error: The function "median" does not exist. (0.7–60) Script error: The function "median" does not exist. (1.36–52) Script error: The function "median" does not exist. (0.3–1.01) Script error: The function "median" does not exist. (0.35–9.24) Estrogen
Estriol E3; 16α-OH-17β-E2 Script error: The function "median" does not exist. (4.03–56) Script error: The function "median" does not exist. (14.0–44.6) Script error: The function "median" does not exist. (0.35–1.4) Script error: The function "median" does not exist. (0.63–0.7) Estrogen
Estetrol E4; 15α,16α-Di-OH-17β-E2 4.0 3.0 4.9 19 Estrogen
Alfatradiol 17α-Estradiol Script error: The function "median" does not exist. (7–80.1) Script error: The function "median" does not exist. (2–42) 0.2–0.52 0.43–1.2 Metabolite
16-Epiestriol 16β-Hydroxy-17β-estradiol Script error: The function "median" does not exist. (4.94–63) 50 ? ? Metabolite
17-Epiestriol 16α-Hydroxy-17α-estradiol Script error: The function "median" does not exist. (29–103) 79–80 ? ? Metabolite
16,17-Epiestriol 16β-Hydroxy-17α-estradiol 1.0 13 ? ? Metabolite
2-Hydroxyestradiol 2-OH-E2 Script error: The function "median" does not exist. (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 Script error: The function "median" does not exist. (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 Script error: The function "median" does not exist. (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 Script error: The function "median" does not exist. (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 Script error: The function "median" does not exist. (68.8–480) Script error: The function "median" does not exist. (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 Script error: The function "median" does not exist. (89.1–468) Script error: The function "median" does not exist. (61.2–295) 0.04 0.05 Estrogen
Hexestrol Dihydrodiethylstilbestrol Script error: The function "median" does not exist. (31–302) 60–234 0.06 0.06 Estrogen
Dienestrol Dehydrostilbestrol Script error: The function "median" does not exist. (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 Script error: The function "median" does not exist. (0.1–47) Script error: The function "median" does not exist. (0.28–6) 3.4–9.69 2.5 SERM
Afimoxifene 4-Hydroxytamoxifen; 4-OHT Script error: The function "median" does not exist. (1.7–257) Script error: The function "median" does not exist. (0.98–339) Script error: The function "median" does not exist. (0.1–3.61) 0.04–4.8 SERM
Toremifene 4-Chlorotamoxifen; 4-CT ? ? 7.14–20.3 15.4 SERM
Clomifene MRL-41 Script error: The function "median" does not exist. (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 – Script error: The function "median" does not exist. (7.8–69) Script error: The function "median" does not exist. (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 2.63 1.22 ? ? SERM
Bazedoxifene – ? ? 0.053 ? SERM
Etacstil GW-5638 4.30 11.5 ? ? SERM
ICI-164,384 – Script error: The function "median" does not exist. (3.70–97.7) 166 0.2 0.08 Antiestrogen
Fulvestrant ICI-182,780 Script error: The function "median" does not exist. (9.4–325) Script error: The function "median" does not exist. (2.05–40.5) 0.42 1.3 Antiestrogen
Propylpyrazoletriol PPT Script error: The function "median" does not exist. (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 – Script error: The function "median" does not exist. (0.0117–94) Script error: The function "median" does not exist. (0.41–185) 0.14–80.0 0.07–27.0 Xenoestrogen
Genistein – Script error: The function "median" does not exist. (0.0012–16) Script error: The function "median" does not exist. (0.86–87) 2.6–126 0.3–12.8 Xenoestrogen
Equol – 0.2–0.287 Script error: The function "median" does not exist. (0.10–2.85) ? ? Xenoestrogen
Daidzein – Script error: The function "median" does not exist. (0.0018–9.3) Script error: The function "median" does not exist. (0.04–17.1) 2.0 85.3 Xenoestrogen
Biochanin A – Script error: The function "median" does not exist. (0.022–0.15) Script error: The function "median" does not exist. (0.010–1.2) 174 8.9 Xenoestrogen
Kaempferol – Script error: The function "median" does not exist. (0.029–0.10) Script error: The function "median" does not exist. (0.002–3.00) ? ? Xenoestrogen
Naringenin – Script error: The function "median" does not exist. (<0.001–0.01) Script error: The function "median" does not exist. (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 – Script error: The function "median" does not exist. (13–52.5) ? ? ? Xenoestrogen
β-Zearalenol – Script error: The function "median" does not exist. (0.032–13) ? ? ? Xenoestrogen
Zeranol α-Zearalanol 48–111 ? ? ? Xenoestrogen
Taleranol β-Zearalanol Script error: The function "median" does not exist. (13–17.8) 14 0.8 0.9 Xenoestrogen
Zearalenone ZEN Script error: The function "median" does not exist. (2.04–28) Script error: The function "median" does not exist. (2.43–31.5) ? ? Xenoestrogen
Zearalanone ZAN 0.51 ? ? ? Xenoestrogen
Bisphenol A BPA Script error: The function "median" does not exist. (0.008–1.0) Script error: The function "median" does not exist. (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 – Script error: The function "median" does not exist. ? ? ? Xenoestrogen
Methoxychlor p,p'-Dimethoxy-DDT Script error: The function "median" does not exist. (<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 Script error: The function "median" does not exist. (<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 Script error: The function "median" does not exist. (<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 Script error: The function "median" does not exist. (0.0015–<0.1) Script error: The function "median" does not exist. (0.01–0.3) 152 1084 Progestogen
Norethynodrel 5(10)-Norethisterone Script error: The function "median" does not exist. (0.3–0.7) <0.1–0.22 14 53 Progestogen
Tibolone 7α-Methylnorethynodrel Script error: The function "median" does not exist. (0.45–2.0) 0.2–0.076 ? ? Progestogen
Δ4-Tibolone 7α-Methylnorethisterone 0.069–<0.1 0.027–<0.1 ? ? Progestogen
3α-Hydroxytibolone – Script error: The function "median" does not exist. (1.06–5.0) 0.6–0.8 ? ? Progestogen
3β-Hydroxytibolone – Script error: The function "median" does not exist. (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.

List of nonsteroidal estrogens

Synthetic

Pharmaceutical

SERMs like tamoxifen and raloxifene can also be considered to be nonsteroidal estrogens in some tissues.[8]

Environmental

Natural

See also

References

  1. ↑ 1.0 1.1 "Non-steroidal steroid receptor modulators". IDrugs 9 (7): 488–94. 2006. doi:10.2174/0929867053764671. PMID 16821162. 
  2. ↑ 2.0 2.1 "The nonsteroidal effects of diethylstilbestrol: the rationale for androgen deprivation therapy without estrogen deprivation in the treatment of prostate cancer". J. Urol. 170 (5): 1703–8. 2003. doi:10.1097/01.ju.0000077558.48257.3d. PMID 14532759. 
  3. ↑ "Diethylstilbestrol (DES) update: recommendations for the identification and management of DES-exposed individuals". J Midwifery Womens Health 48 (1): 19–29. 2003. doi:10.1016/s1526-9523(02)00370-7. PMID 12589302. 
  4. ↑ "Diethylstilbestrol exposure". Am Fam Physician 69 (10): 2395–400. 2004. PMID 15168959. 
  5. ↑ Philipp Y. Maximov; Russell E. McDaniel; V. Craig Jordan (23 July 2013). Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 4–. ISBN 978-3-0348-0664-0. https://books.google.com/books?id=p-W5BAAAQBAJ&pg=PA4. 
  6. ↑ Edward P. Gelmann; Charles L. Sawyers; Frank J. Rauscher, III (19 December 2013). Molecular Oncology. Cambridge University Press. pp. 885–. ISBN 978-0-521-87662-9. https://books.google.com/books?id=GrZEAgAAQBAJ&pg=PA885. 
  7. ↑ "Endocrine disruptors: can biological effects and environmental risks be predicted?". Regul. Toxicol. Pharmacol. 36 (1): 118–30. 2002. doi:10.1006/rtph.2002.1564. PMID 12383724. 
  8. ↑ V. Craig Jordan (2013). Estrogen Action, Selective Estrogen Receptor Modulators, and Women's Health: Progress and Promise. World Scientific. pp. 362–365. ISBN 978-1-84816-958-6. https://books.google.com/books?id=ejS6CgAAQBAJ&pg=PA362. 

Further reading



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