Chemistry:Comparison of estrogens
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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.
Pharmacodynamics
Affinities and efficacies
| Estrogen | ERα (%) | ERβ (%) |
| Estradiol | 100 | 100 |
| Estrone | 60 | 37 |
| Estriol | 14 | 21 |
| Ethinylestradiol | 190 | 11[3] |
| 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 |
| 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 |
| 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 |
See also
References
- ↑ "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 Suppl 1: 3–63. 2005. doi:10.1080/13697130500148875. PMID 16112947. http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf.
- ↑ "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology 138 (3): 863–70. 1997. doi:10.1210/endo.138.3.4979. PMID 9048584.
- ↑ "Differential Response of Estrogen Receptor α and Estrogen Receptor β to Partial Estrogen Agonists/Antagonists". Molecular Pharmacology 54 (1): 105-112. 1998. doi:10.1124/mol.54.1.105. PMID 9658195. http://molpharm.aspetjournals.org/content/54/1/105.long.
- ↑ "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta". Biochem. Pharmacol. 71 (10): 1459–69. 2006. doi:10.1016/j.bcp.2006.02.002. PMID 16554039.
- ↑ "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. 2000. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.
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