Comparison of estrogens

Estradiol, a major estrogen and both a hormone and a medication.

This is a comparison of estrogens, or agonists of the estrogen receptor (ER). Estrogens include both natural estrogens like estradiol and synthetic estrogens like ethinylestradiol and diethylstilbestrol.

Affinities and efficacies

Relative binding affinities of estrogens[1][2]
Estrogen ERα (%) ERβ (%)
Estradiol 100 100
Estrone 60 37
Estriol 14 21
17α-Estradiol 58 11
4-Hydroxyestradiol 13 7
2-Hydroxyestradiol 7 11
Estrone 3-sulfate <1 <1
Moxestrol 43 5
Diethylstilbestrol 468 295
Hexestrol 302 234
Dienestrol 223 404
Tamoxifen 7 6
4-Hydroxytamoxifen 178 339
Clomifene 25 12
Nafoxidine 44 16
ICI-164384 85 166
5-Androstenediol 6 17
4-Androstenediol 0.5 0.6
3β-Androstanediol 3 7
3α-Androstanediol 0.07 0.3
Dehydroepiandrosterone 0.04 0.07
4-Androstenedione <0.01 <0.01
Coumestrol 94 185
Genistein 5 36
β-Zearalanol 16 14
Bisphenol A 0.05 0.33
Relative binding affinities + transactivation capacities of estrogens[3]
RBA
RTC
Estrogen
 ERα (%) ERβ (%) ERα (%) ERβ (%)
Estradiol 100 100 100 100
Estrone 4.0 3.5 2.6 4.3
Estriol 11.3 17.6 10.6 16.6
Ethinylestradiol 233 37.8 213 27.2
Propylpyrazoletriol 10.0 0.12 20.0 ND
16α-LE2 14.6 0.089 18.9 0.07
Diarylpropionitrile 0.12 6.6 0.063 3.0
8β-VE2 0.35 22.0 0.11 34.0
Fulvestrant 9.4 8.3 ND ND
4-Hydroxytamoxifen 1.7 2.3 ND ND
Raloxifene 7.8 0.54 ND ND
Genistein 0.032 0.86 0.045 1.2
Biochanin A 0.022 1.2 0.021 1.0
Coumestrol 0.05 0.41 0.11 1.0
Daidzein 0.015 0.13 0.011 0.12
ER (rat uterine cytosol) RBA + estrogenicity (change in rat uterine wet weight) of estrogen metabolites[4]
Compound RBA Uterine weight (%)
Control – 100
Estradiol 100 506
Estriol 10 468
2-Hydroxyestradiol 24 285
2-Methoxyestradiol 0.05 101
4-Hydroxyestradiol 45 ?
4-Methoxyestradiol 13 260
2-Hydroxyestrone 2 130
2-Methoxyestrone 0.01 ?
4-Hydroxyestrone 11 351
4-Methoxyestrone 0.13 338

Oral potencies by weight

Relative oral potency (by weight) of major clinically used estrogens[1]
Estrogen Hot flashes FSH HDL cholesterol SHBG CBG Angiotensinogen
Estradiol 100 100 100 100 100 100
Estriol 30 30 20 ? ? ?
Estrone sulfate ? 90 50 90 70 150
CEEs 120 110 150 300 150 500
Equilin sulfate ? ? 600 750 600 750
Ethinylestradiol 12,000 12,000 40,000 50,000 60,000 35,000
Diethylstilbestrol ? 340 ? 2,560 2,450 1,950
Hot flashes = clinical relief of hot flashes; FSH = suppression of FSH levels; HDL cholesterol, SHBG, CBG,
and angiotensinogen = increase in the serum levels of these hepatic proteins.

See also

References

  1. 1 2 Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. PMID 16112947. doi:10.1080/13697130500148875.
  2. ↑ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–70. PMID 9048584. doi:10.1210/endo.138.3.4979.
  3. ↑ Escande A, Pillon A, Servant N, Cravedi JP, Larrea F, Muhn P, Nicolas JC, Cavaillès V, Balaguer P (2006). "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta". Biochem. Pharmacol. 71 (10): 1459–69. PMID 16554039. doi:10.1016/j.bcp.2006.02.002.
  4. ↑ Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". J. Soc. Gynecol. Investig. 7 (3): 175–83. PMID 10865186. doi:10.1016/s1071-5576(00)00049-6.


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