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Human drug metabolites
17β-Dihydroequilin
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    17β-Dihydroequilin

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    Not to be confused with 17α-Dihydroequilin, 17α-Dihydroequilenin, or 17β-Dihydroequilenin.
    17β-Dihydroequilin
    17β-Dihydroequilin.svg
    Clinical data
    Other names β-Dihydroequilin; Δ7-17β-Estradiol; 7-Dehydro-17β-estradiol; Estra-1,3,5(10),7-tetraen-3,17β-diol; NSC-12170
    Routes of
    administration    		 By mouth
    Drug class Estrogen
    Identifiers
    • (9S,13S,14S,17S)-13-Methyl-6,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthrene-3,17-diol
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.020.576
    Chemical and physical data
    Formula C18H22O2
    Molar mass 270.372 g·mol−1
    3D model (JSmol)
    • C[C@]12CC[C@H]3C(=CCC4=C3C=CC(=C4)O)[C@@H]1CC[C@@H]2O
    • InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16-17,19-20H,2,6-9H2,1H3/t14-,16+,17+,18+/m1/s1
    • Key:NLLMJANWPUQQTA-UBDQQSCGSA-N

    17β-Dihydroequilin is a naturally occurring estrogen sex hormone found in horses as well as a medication. As the C3 sulfate ester sodium salt, it is a minor constituent (1.7%) of conjugated estrogens (CEEs; brand name Premarin). However, as equilin, with equilin sulfate being a major component of CEEs, is transformed into 17β-dihydroequilin in the body, analogously to the conversion of estrone into estradiol, 17β-dihydroequilin is, along with estradiol, the most important estrogen responsible for the effects of CEEs.

    Pharmacology

    Pharmacodynamics

    17β-Dihydroequilin is an estrogen, or an agonist of the estrogen receptors (ERs), the ERα and ERβ. In terms of relative binding affinity for the ERs, 17β-dihydroequilin has about 113% and 108% of that of estradiol for the ERα and ERβ, respectively. 17β-Dihydroequilin has about 83% of the relative potency of CEEs in the vagina and 200% of the relative potency of CEEs in the uterus. Of the equine estrogens, it shows the highest estrogenic activity and greatest estrogenic potency.

    Like CEEs as a whole, 17β-dihydroequilin has disproportionate effects in certain tissues such as the liver and uterus.Equilin, the second major component of conjugated estrogens after estrone, is reversibly transformed into 17β-dihydroequilin analogously to the transformation of estrone into estradiol. However, whereas the balance of mutual interconversion of estrone and estradiol is largely shifted in the direction of estrone, it is nearly equal in the case of equilin and 17β-dihydroequilin. As such, although 17β-dihydroequilin is only a minor constituent of CEEs, it is, along with estradiol, the most important estrogen relevant to the estrogenic activity of the medication.

    Relative oral potencies of estrogens
    Estrogen HF VE UCa FSH LH HDL-C SHBG CBG AGT Liver
    Estradiol 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0
    Estrone ? ? ? 0.3 0.3 ? ? ? ? ?
    Estriol 0.3 0.3 0.1 0.3 0.3 0.2 ? ? ? 0.67
    Estrone sulfate ? 0.9 0.9 0.8–0.9 0.9 0.5 0.9 0.5–0.7 1.4–1.5 0.56–1.7
    Conjugated estrogens 1.2 1.5 2.0 1.1–1.3 1.0 1.5 3.0–3.2 1.3–1.5 5.0 1.3–4.5
    Equilin sulfate ? ? 1.0 ? ? 6.0 7.5 6.0 7.5 ?
    Ethinylestradiol 120 150 400 60–150 100 400 500–600 500–600 350 2.9–5.0
    Diethylstilbestrol ? ? ? 2.9–3.4 ? ? 26–28 25–37 20 5.7–7.5
    Sources and footnotes
    Notes: Values are ratios, with estradiol as standard (i.e., 1.0). Abbreviations: HF = Clinical relief of hot flashes. VE = Increased proliferation of vaginal epithelium. UCa = Decrease in UCa. FSH = Suppression of FSH levels. LH = Suppression of LH levels. HDL-C, SHBG, CBG, and AGT = Increase in the serum levels of these liver proteins. Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (hot flashes/gonadotropins). Sources: See template.

    Pharmacokinetics

    17β-Dihydroequilin has about 30% of the relative binding affinity of testosterone for sex hormone-binding globulin (SHBG), relative to 50% for estradiol. The metabolic clearance rate of 17β-dihydroequilin is 1,250 L/day/m2, relative to 580 L/day/m2 for estradiol.

    Chemistry

    See also: List of estrogens § Equine estrogens

    17β-Dihydroequilin, or simply β-dihydroequilin, also known as δ7-17β-estradiol or as 7-dehydro-17β-estradiol, as well as estra-1,3,5(10),7-tetraen-3,17β-diol, is a naturally occurring estrane steroid and an analogue of estradiol. In terms of chemical structure and pharmacology, equilin (δ7-estrone) is to 17β-dihydroequilin as estrone is to estradiol.



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