17β-Dihydroequilenin
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| Clinical data | |
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| Synonyms | β-Dihydroequilenin; Δ6,8-17β-Estradiol; 6,8-Didehydro-17β-estradiol; Estra-1,3,5(10),6,8-pentaen-3,17β-diol |
| Routes of administration | By mouth |
| Drug class | Estrogen |
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| Chemical and physical data | |
| Formula | C18H20O2 |
| Molar mass | 268.350 g/mol g·mol−1 |
| 3D model (JSmol) | |
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17β-Dihydroequilenin, or β-dihydroequilenin, also known as δ6,8-17β-estradiol or 6,8-didehydro-17β-estradiol, as well as estra-1,3,5(10),6,8-pentaen-3,17β-diol, is a naturally occurring steroidal estrogen found in horses which is closely related to equilin, equilenin, and estradiol, and, as the 3-sulfate ester sodium salt, is a minor constituent (0.5%) of conjugated estrogens (Premarin).[1] 17β-Dihydroequilenin has unexpectedly shown a selective estrogen receptor modulator (SERM)-like profile of estrogenic activity in studies with monkeys, in which beneficial effects on bone and the cardiovascular system were noted but proliferative responses in breast and endometrium were not observed.[2]
| Compound | Synonym | Proportion (%) | Relative potency in the vagina (%) |
Relative potency in the uterus (%) |
RBA for ERα (%) |
RBA for ERβ (%) |
ERα / ERβ RBA ratio |
|---|---|---|---|---|---|---|---|
| Conjugated estrogens | – | 100 | 38 | 100 | – | – | – |
| Estrone | – | 49.1–61.5 | 30 | 32 | 26 | 52 | 0.50 |
| Equilin | Δ7-Estrone | 22.4–30.5 | 42 | 80 | 13 | 49 | 0.26 |
| 17α-Dihydroequilin | Δ7-17α-Estradiol | 13.5–19.5 | 0.06 | 2.6 | 41 | 32 | 1.30 |
| 17α-Estradiol | – | 2.5–9.5 | 0.11 | 3.5 | 19 | 42 | 0.45 |
| Δ8-Estrone | – | 3.5–3.9 | ? | ? | 19 | 32 | 0.60 |
| Equilenin | Δ6,8-Estrone | 2.2–2.8 | 1.3 | 11.4 | 15 | 20–29 | 0.50–0.75 |
| 17β-Dihydroequilin | Δ7-17β-Estradiol | 0.5–4.0 | 83 | 200 | 113 | 108 | 1.05 |
| 17α-Dihydroequilenin | Δ6,8-17α-Estradiol | 1.2–1.6 | 0.018 | 1.3 | 20 | 49 | 0.40 |
| 17β-Estradiol | – | 0.56–0.9 | 100 | ? | 100 | 100 | 1.00 |
| 17β-Dihydroequilenin | Δ6,8-17β-Estradiol | 0.5–0.7 | 0.21 | 9.4 | 68 | 90 | 0.75 |
| Δ8-17β-Estradiol | – | Small amounts | ? | ? | 68 | 72 | 0.94 |
| Notes: All listed compounds are present in conjugated estrogen products specifically in the form of the sodium salts of the sulfate esters (i.e., as sodium estrone sulfate, sodium equilin sulfate, etc.). Sources: See template. | |||||||
See also[edit]
References[edit]
- ^ Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
- ^ Cline JM (2007). "Assessing the mammary gland of nonhuman primates: effects of endogenous hormones and exogenous hormonal agents and growth factors". Birth Defects Res. B Dev. Reprod. Toxicol. 80 (2): 126–46. doi:10.1002/bdrb.20112. PMID 17443713.
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