17α-Dihydroequilin
17α-Dihydroequilin, or α-dihydroequilin, also known as 7-dehydro-17α-estradiol, as well as estra-1,3,5(10),7-tetraene-3,17α-diol, is a naturally occurring steroidal estrogen found in horses which is closely related to equilin, equilenin, and 17α-estradiol.[1][2] The compound, as the 3-sulfate ester sodium salt, is present in conjugated estrogens (Premarin), a pharmaceutical extract of the urine of pregnant mares, and is the third highest quantity constituent in the formulation (13.8%).[1] The compound has been studied clinically.[3]
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. |
![]() | |
Clinical data | |
---|---|
Other names | α-Dihydroequilin; 7-Dehydro-17α-estradiol; Estra-1,3,5(10),7-tetraen-3,17α-diol |
Routes of administration | By mouth |
Drug class | Estrogen |
ATC code | |
Identifiers | |
IUPAC name
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
ECHA InfoCard | 100.010.440 ![]() |
Chemical and physical data | |
Formula | C18H22O2 |
Molar mass | 270.366 g/mol g·mol−1 |
3D model (JSmol) | |
SMILES
| |
InChI
|
See also
References
- Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
- IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 378–. ISBN 978-92-832-1291-1.
- Wilcox, John G.; Stanczyk, Frank Z.; Morris, Randy S.; Gentzschein, Elisabet; Lobo, Rogerio A. (1996). "Biologic effects of 17α-dihydroequilin sulfate". Fertility and Sterility. 66 (5): 748–752. doi:10.1016/S0015-0282(16)58629-4. ISSN 0015-0282.
This article is issued from
Wikipedia.
The text is licensed under Creative
Commons - Attribution - Sharealike.
Additional terms may apply for the media files.