8,9-Dehydroestradiol

8,9-Dehydroestradiol, or Δ8-17β-estradiol, also known as estra-1,3,5(10),8-tetraen-17β-ol-3-one, 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 of conjugated estrogens (Premarin).[1] It is also an important active metabolite of 8,9-dehydroestrone, analogously to conversion of estrone or estrone sulfate into estradiol.[2][3]

Composition of conjugated estrogens and properties of constituents
CompoundSynonymProportion (%)Relative potency
in the vagina (%)
Relative potency
in the uterus (%)
RBA for
ERα (%)
RBA for
ERβ (%)
ERα / ERβ
RBA ratio
Conjugated estrogens10038100
Estrone49.1–61.5303226520.50
EquilinΔ7-Estrone22.4–30.5428013490.26
17α-DihydroequilinΔ7-17α-Estradiol13.5–19.50.062.641321.30
17α-Estradiol2.5–9.50.113.519420.45
Δ8-Estrone3.5–3.9??19320.60
EquileninΔ6,8-Estrone2.2–2.81.311.41520–290.50–0.75
17β-DihydroequilinΔ7-17β-Estradiol0.5–4.0832001131081.05
17α-DihydroequileninΔ6,8-17α-Estradiol1.2–1.60.0181.320490.40
17β-Estradiol0.56–0.9100?1001001.00
17β-DihydroequileninΔ6,8-17β-Estradiol0.5–0.70.219.468900.75
Δ8-17β-EstradiolSmall amounts??68720.94
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.
8,9-Dehydroestradiol
Clinical data
Other namesΔ8-Estradiol; Δ8-17β-Estradiol; Estra-1,3,5(10),8-tetraen-17β-ol-3-one
Routes of
administration
By mouth
Drug classEstrogen
Identifiers
CAS Number
ChemSpider
Chemical and physical data
FormulaC18H22O2
Molar mass270.372 g·mol−1
3D model (JSmol)

See also

References

  1. Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
  2. Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.
  3. Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "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. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.



This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.