8,9-Dehydroestradiol Explained

Iupac Name:	(13S,14S,17S)-13-methyl-6,7,11,12,14,15,16,17-octahydrocyclopenta[''a'']phenanthrene-3,17-diol
Width:	225px
Routes Of Administration:	By mouth
Class:	Estrogen
Cas Number:	23392-54-3
Chemspiderid:	8014038
Synonyms:	Δ⁸-Estradiol; Δ⁸-17β-Estradiol; Estra-1,3,5(10),8-tetraen-17β-ol-3-one
C:	18
H:	22
O:	2
Smiles:	Oc4cc3c(/C1=C(/[C@@H]2CC[C@H](O)[C@]2(CC1)C)CC3)cc4
Stdinchi:	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
Stdinchikey:	UWYDUSMQFLTKBQ-BZSNNMDCSA-N

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]

Notes and References

Book: Fritz MA, Speroff L . Clinical Gynecologic Endocrinology and Infertility. 28 March 2012. Lippincott Williams & Wilkins. 978-1-4511-4847-3. 751–.
Kuhl H . Pharmacology of estrogens and progestogens: influence of different routes of administration . Climacteric . 8 . Suppl 1 . 3–63 . August 2005 . 16112947 . 10.1080/13697130500148875 . 24616324 .
Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK . Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women . Journal of the Society for Gynecologic Investigation . 7 . 3 . 175–183 . 2000 . 10865186 . 10.1016/s1071-5576(00)00049-6 .