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Estrogen conjugate - Wikipedia
Wikipedia

Estrogen conjugate

Not to be confused with Conjugated estrogens.

An estrogen conjugate is a conjugate of an endogenous estrogen. They occur naturally in the body as metabolites of estrogens and can be reconverted back into estrogens. They serve as a circulating reservoir for estrogen, particularly in the case of orally administered pharmaceutical estradiol. Estrogen conjugates include sulfate and/or glucuronide conjugates of estradiol, estrone, and estriol:

Estrone sulfate, the 3-sulfate conjugate of estrone.
Estriol glucuronide, the 16αあるふぁ-glucuronide conjugate of estriol.

Estrogen conjugates are conjugated at the C3, C16αあるふぁ, and/or C17βべーた positions, where hydroxyl groups are available.[1]

Estrogen conjugates have been used as pharmaceutical estrogens, as in estrone sulfate as estropipate (piperazine estrone sulfate) and in conjugated estrogens (Premarin) and conjugated estriol (Progynon, Emmenin).

Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
Estrogen Other names RBATooltip Relative binding affinity (%)a REP (%)b
ER ERαあるふぁ ERβべーた
Estradiol E2 100 100 100
Estradiol 3-sulfate E2S; E2-3S ? 0.02 0.04
Estradiol 3-glucuronide E2-3G ? 0.02 0.09
Estradiol 17βべーた-glucuronide E2-17G ? 0.002 0.0002
Estradiol benzoate EB; Estradiol 3-benzoate 10 1.1 0.52
Estradiol 17βべーた-acetate E2-17A 31–45 24 ?
Estradiol diacetate EDA; Estradiol 3,17βべーた-diacetate ? 0.79 ?
Estradiol propionate EP; Estradiol 17βべーた-propionate 19–26 2.6 ?
Estradiol valerate EV; Estradiol 17βべーた-valerate 2–11 0.04–21 ?
Estradiol cypionate EC; Estradiol 17βべーた-cypionate ?c 4.0 ?
Estradiol palmitate Estradiol 17βべーた-palmitate 0 ? ?
Estradiol stearate Estradiol 17βべーた-stearate 0 ? ?
Estrone E1; 17-Ketoestradiol 11 5.3–38 14
Estrone sulfate E1S; Estrone 3-sulfate 2 0.004 0.002
Estrone glucuronide E1G; Estrone 3-glucuronide ? <0.001 0.0006
Ethinylestradiol EE; 17αあるふぁ-Ethynylestradiol 100 17–150 129
Mestranol EE 3-methyl ether 1 1.3–8.2 0.16
Quinestrol EE 3-cyclopentyl ether ? 0.37 ?
Footnotes: a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC50) that were determined via in-vitro βべーた‐galactosidase (βべーた-gal) and green fluorescent protein (GFP) production assays in yeast expressing human ERαあるふぁ and human ERβべーた. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure). Sources: See template page.
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.

See also edit

References edit

  1. ^ Bhavnani, BR (January 1998). "Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism". Proceedings of the Society for Experimental Biology and Medicine. 217 (1): 6–16. doi:10.3181/00379727-217-44199. PMID 9421201. S2CID 45177839.
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