8,9-Dehydroestradiol

8,9-Dehydroestradiol
Clinical data
Other names	Δ8-Estradiol; Δ8-17β-Estradiol; Estra-1,3,5(10),8-tetraen-17β-ol-3-one
Routes of; administration	By mouth
Drug class	Estrogen
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	270.372 g·mol−1
3D model (JSmol)	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 Δ⁸-17β-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]

References

^ Fritz MA, Speroff L (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
^ Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
^ 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". Journal of the Society for Gynecologic Investigation. 7 (3): 175–183. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.

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Clinical data

Other names	Δ⁸-Estradiol; Δ⁸-17β-Estradiol; Estra-1,3,5(10),8-tetraen-17β-ol-3-one
Routes of administration	By mouth
Drug class	Estrogen
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	270.372 g·mol⁻¹
3D model (JSmol)	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