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	270.366 g/mol 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]

Composition of conjugated estrogens and properties of constituents
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	Δ^6,8-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	Δ^6,8-17α-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	Δ^6,8-17β-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.

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.
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.
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.

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[FritzSperoff2012-1] Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.

[pmid16112947-2] 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.

[pmid10865186-3] 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.

8,9-Dehydroestradiol

See also

References