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Stilbestrol

From Wikipedia, the free encyclopedia
Not to be confused with Diethylstilbestrol.
Stilbestrol
Names
Preferred IUPAC name
4,4′-[(E)-Ethene-1,2-diyl]diphenol
Other names
Dihydroxystilbene; 4,4'-Dihydroxystilbene, 4,4'-stilbenediol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C14H12O2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h1-10,15-16H/b2-1+
    Key: XLAIWHIOIFKLEO-OWOJBTEDSA-N
  • C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O
  • c1cc(ccc1/C=C/c2ccc(cc2)O)O
Properties
C14H12O2
Molar mass 212.24388 g/mol
-130·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid nonsteroidal estrogen[1] and the parent compound of a group of more potent nonsteroidal estrogen derivatives that includes, most notably, diethylstilbestrol (DES).[1][2][3] The term "stilbestrol" is often used incorrectly to refer to DES, but they are not the same compound.[2]

Stilbestrol itself is an active estrogen but is less potent than DES and other derivatives.[1]

Stilbestrol derivatives

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The stilbestrol estrogenic drugs include the following:

Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol are the most well-known.[4]

Mechanism of action

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The stilbestrol estrogens bind with high affinity to both ERαあるふぁ and ERβべーた.[5]

Affinities of estrogen receptor ligands for the ERαあるふぁ and ERβべーた
Ligand Other names Relative binding affinities (RBA, %)a Absolute binding affinities (Ki, nM)a Action
ERαあるふぁ ERβべーた ERαあるふぁ ERβべーた
Estradiol E2; 17βべーた-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あるふぁ-OH-17βべーた-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あるふぁ,16αあるふぁ-Di-OH-17βべーた-E2 4.0 3.0 4.9 19 Estrogen
Alfatradiol 17αあるふぁ-Estradiol 20.5 (7–80.1) 8.195 (2–42) 0.2–0.52 0.43–1.2 Metabolite
16-Epiestriol 16βべーた-Hydroxy-17βべーた-estradiol 7.795 (4.94–63) 50 ? ? Metabolite
17-Epiestriol 16αあるふぁ-Hydroxy-17αあるふぁ-estradiol 55.45 (29–103) 79–80 ? ? Metabolite
16,17-Epiestriol 16βべーた-Hydroxy-17αあるふぁ-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あるふぁ-Hydroxyestrone 16αあるふぁ-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べーた-disulfate 0.0004 ? ? ? Metabolite
Estradiol 3-glucuronide E2-3G 0.0079 ? ? ? Metabolite
Estradiol 17βべーた-glucuronide E2-17G 0.0015 ? ? ? Metabolite
Estradiol 3-gluc. 17βべーた-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べーた-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べーた-Dihydroequilin 7-Dehydro-17βべーた-estradiol 7.9–113 7.9–108 0.09 0.17 Estrogen
17αあるふぁ-Dihydroequilin 7-Dehydro-17αあるふぁ-estradiol 18.6 (18–41) 14–32 0.24 0.57 Estrogen
17βべーた-Dihydroequilenin 6,8-Didehydro-17βべーた-estradiol 35–68 90–100 0.15 0.20 Estrogen
17αあるふぁ-Dihydroequilenin 6,8-Didehydro-17αあるふぁ-estradiol 20 49 0.50 0.37 Estrogen
Δでるた8-Estradiol 8,9-Dehydro-17βべーた-estradiol 68 72 0.15 0.25 Estrogen
Δでるた8-Estrone 8,9-Dehydroestrone 19 32 0.52 0.57 Estrogen
Ethinylestradiol EE; 17αあるふぁ-Ethynyl-17βべーた-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べーた-Methoxy-EE 35–43 5–20 0.5 2.6 Estrogen
Methylestradiol 17αあるふぁ-Methyl-17βべーた-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あるふぁ agonist
16αあるふぁ-LE2 16αあるふぁ-Lactone-17βべーた-estradiol 14.6–57 0.089 0.27 131 ERαあるふぁ agonist
16αあるふぁ-Iodo-E2 16αあるふぁ-Iodo-17βべーた-estradiol 30.2 2.30 ? ? ERαあるふぁ agonist
Methylpiperidinopyrazole MPP 11 0.05 ? ? ERαあるふぁ antagonist
Diarylpropionitrile DPN 0.12–0.25 6.6–18 32.4 1.7 ERβべーた agonist
8βべーた-VE2 8βべーた-Vinyl-17βべーた-estradiol 0.35 22.0–83 12.9 0.50 ERβべーた agonist
Prinaberel ERB-041; WAY-202,041 0.27 67–72 ? ? ERβべーた agonist
ERB-196 WAY-202,196 ? 180 ? ? ERβべーた agonist
Erteberel SERBA-1; LY-500,307 ? ? 2.68 0.19 ERβべーた agonist
SERBA-2 – ? ? 14.5 1.54 ERβべーた 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べーた-Sitosterol – <0.001–0.0875 <0.001–0.016 ? ? Xenoestrogen
Resveratrol – <0.001–0.0032 ? ? ? Xenoestrogen
αあるふぁ-Zearalenol – 48 (13–52.5) ? ? ? Xenoestrogen
βべーた-Zearalenol – 0.6 (0.032–13) ? ? ? Xenoestrogen
Zeranol αあるふぁ-Zearalanol 48–111 ? ? ? Xenoestrogen
Taleranol βべーた-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あるふぁ-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あるふぁ-Androstanediol 3αあるふぁ-Adiol 0.07 0.3 260 48 Androgen
3βべーた-Androstanediol 3βべーた-Adiol 3 7 6 2 Androgen
Androstanedione 5αあるふぁ-Androstanedione <0.01 <0.01 >10000 >10000 Androgen
Etiocholanedione 5βべーた-Androstanedione <0.01 <0.01 >10000 >10000 Androgen
Methyltestosterone 17αあるふぁ-Methyltestosterone <0.0001 ? ? ? Androgen
Ethinyl-3αあるふぁ-androstanediol 17αあるふぁ-Ethynyl-3αあるふぁ-adiol 4.0 <0.07 ? ? Estrogen
Ethinyl-3βべーた-androstanediol 17αあるふぁ-Ethynyl-3βべーた-adiol 50 5.6 ? ? Estrogen
Progesterone P4; 4-Pregnenedione <0.001–0.6 <0.001–0.010 ? ? Progestogen
Norethisterone NET; 17αあるふぁ-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あるふぁ-Methylnorethynodrel 0.5 (0.45–2.0) 0.2–0.076 ? ? Progestogen
Δでるた4-Tibolone 7αあるふぁ-Methylnorethisterone 0.069–<0.1 0.027–<0.1 ? ? Progestogen
3αあるふぁ-Hydroxytibolone – 2.5 (1.06–5.0) 0.6–0.8 ? ? Progestogen
3βべーた-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あるふぁ and ERβべーた proteins (except the ERβべーた values from Kuiper et al. (1997), which are rat ERβべーた). Sources: See template page.
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Triphenylethylene.

Estrogens closely related to the stilbestrols include paroxypropione (a metabolite of diethylstilbestrol) and the anise and fennel-derived compounds anol, dianol, anethole, dianethole, and photoanethole (from which the stilbestrol estrogens were actually originally derived). The triphenylethylene group of estrogenic drugs that includes triphenylethylene itself, estrobin, chlorotrianisene, broparestrol, ethamoxytriphetol, clomifene, tamoxifen, and more recently developed derivatives is also very closely related structurally to the stilbestrols.

Resveratrol is a stilbenoid with estrogenic properties that is not technically a stilbestrol derivative (it is 3,4',5-stilbenetriol).[6]

Occupational exposure

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Occupational exposure to stilbestrol has resulted in gynaecomastia in workers.[7]

See also

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References

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  1. ^ a b c Noller KL, Fish CR (July 1974). "Diethylstilbestrol usage: Its interesting past, important present, and questionable future". Med. Clin. North Am. 58 (4): 793–810. doi:10.1016/s0025-7125(16)32122-8. PMID 4276416.
  2. ^ a b VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
  3. ^ William John Edward Jessop (12 May 2014). Fearon's Introduction to Biochemistry. Elsevier. pp. 408–. ISBN 978-1-4831-9556-8.
  4. ^ Actions and Uses of Drugs. Stanford University Press. pp. 234–. ISBN 978-0-8047-1505-8.
  5. ^ Kuiper, George G. J. M.; Carlsson, Bo; Grandien, Kaj; Enmark, Eva; Häggblad, Johan; Nilsson, Stefan; Gustafsson, Jan-Åke (1997). "Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors αあるふぁ and βべーた". Endocrinology. 138 (3): 863–870. doi:10.1210/endo.138.3.4979. ISSN 0013-7227. PMID 9048584.
  6. ^ Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM; Lantvit; Christov; Mehta; Moon; Pezzuto (October 2001). "Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models". Cancer Res. 61 (20): 7456–63. PMID 11606380.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Fitzsimons, P.M. (October 1944). "Gynaecomastia in Stilboestrol Workers". Br J Ind Med. 1 (4): 235–237. PMC 1035620.
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