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17β-Dihydroequilin

Clinical data
Other names	β-Dihydroequilin; Δ-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
IUPAC name (9S,13S,14S,17S)-13-Methyl-6,9,11,12,14,15,16,17-octahydrocyclopentaphenanthrene-3,17-diol
CAS Number	3563-27-7
PubChem CID	11954027
ChemSpider	10128322
UNII	WXG88DST4R
ChEBI	CHEBI:62851
ChEMBL	ChEMBL121458
CompTox Dashboard (EPA)	DTXSID40871892
ECHA InfoCard	100.020.576
Chemical and physical data
Formula	C18H22O2
Molar mass	270.372 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3C(=CCC4=C3C=CC(=C4)O)1CC2O
InChI 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.

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/m, relative to 580 L/day/m for estradiol.

Chemistry

17β-Dihydroequilin, or simply β-dihydroequilin, also known as δ-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 (δ-estrone) is to 17β-dihydroequilin as estrone is to estradiol.

References

1. ^ Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
2. Fritz MA, Speroff L (28 March 2012). "Postmenopausal Hormone Therapy". Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.

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