8,9-Dehydroestradiol

8,9-Dehydroestradiol

Clinical data
Routes of administration	Oral
Identifiers
IUPAC name (13S,14S,17S)-13-Methyl-6,7,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number	23392-54-3
ChemSpider	8014038
Chemical and physical data
Formula	C18H22O2
Molar mass	270.3661 g/mol
3D model (Jmol)	Interactive image
SMILES Oc4cc3c(/C1=C(/[C@@H]2CC[C@H](O)[C@]2(CC1)C)CC3)cc4
InChI 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/h3,5,10,16-17,19-20H,2,4,6-9H2,1H3/t16-,17-,18-/m0/s1 Key:UWYDUSMQFLTKBQ-BZSNNMDCSA-N

8,9-Dehydroestradiol, or Δ⁸-estradiol, also known as estra-1,3,5(10),8-tetraen-17β-ol-3-one, is a naturally occurring steroidal estrogen found in horses that is closely related to equilin, equilenin, and estradiol, and, as the 3-sulfate ester sodium salt, is a minor constituent of conjugated equine 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]

See also

• 17α-Dihydroequilin
• 17β-Dihydroequilin
• 17α-Dihydroequilenin
• 17β-Dihydroequilenin

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. PMID 10865186.