8,9-Dehydroestrone Explained
| Iupac Name: | (13S,14S)-3-Hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6H-cyclopenta[''a'']phenanthren-17-one |
| Width: | 225px |
| Routes Of Administration: | By mouth |
| Class: | Estrogen |
| Cas Number: | 474-87-3 |
| Pubchem: | 6451472 |
| Chemspiderid: | 4953937 |
| Unii: | 7C1N8RKG9F |
| Synonyms: | Δ8-Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one |
| C: | 18 |
| H: | 20 |
| O: | 2 |
| Smiles: | C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O |
| Stdinchi: | 1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,16,19H,2,4,6-9H2,1H3/t16-,18-/m0/s1 |
| Stdinchikey: | OUGSRCWSHMWPQE-WMZOPIPTSA-N |
8,9-Dehydroestrone, or Δ8-estrone, also known as estra-1,3,5(10),8-tetraen-3-ol-17-one, is a naturally occurring estrogen found in horses which is closely related to equilin, equilenin, and estrone, and, as the 3-sulfate ester sodium salt, is a minor constituent (3.5%) of conjugated estrogens (Premarin).[1] [2] [3] [4] It produces 8,9-dehydro-17β-estradiol as an important active metabolite, analogously to conversion of estrone or estrone sulfate into estradiol.[5] The compound was first described in 1997.[6] In addition to 8,9-dehydroestrone and 8,9-dehydro-17β-estradiol, 8,9-dehydro-17α-estradiol is likely also to be present in conjugated estrogens, but has not been identified at this time.
See also
- List of estrogens § Equine estrogens
Notes and References
- Book: Fritz MA, Speroff L . Postmenopausal Hormone Therapy . Clinical Gynecologic Endocrinology and Infertility. https://books.google.com/books?id=KZLubBxJEwEC&pg=PA751 . 28 March 2012. Lippincott Williams & Wilkins. 978-1-4511-4847-3. 751–.
- Bhavnani BR . Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism . Proceedings of the Society for Experimental Biology and Medicine . 217 . 1 . 6–16 . January 1998 . 9421201 . 10.3181/00379727-217-44199 . 45177839 .
- Bhavnani BR, Cecutti A, Gerulath A . Pharmacokinetics and pharmacodynamics of a novel estrogen delta8-estrone in postmenopausal women and men . The Journal of Steroid Biochemistry and Molecular Biology . 67 . 2 . 119–131 . October 1998 . 9877212 . 10.1016/s0960-0760(98)00082-x . 54352249 .
- Baracat E, Haidar M, Lopez FJ, Pickar J, Dey M, Negro-Vilar A . Estrogen activity and novel tissue selectivity of delta8,9-dehydroestrone sulfate in postmenopausal women . The Journal of Clinical Endocrinology and Metabolism . 84 . 6 . 2020–2027 . June 1999 . 10372704 . 10.1210/jcem.84.6.5800 . free .
- 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, Cecutti A, Dey MS . Effects in postmenopausal women of delta-8-estrone sulfate: A novel estrogen component of Premarin. . Journal Society Gynecologic Investigation . 1997 . 4 . 1 (Suppl . 392 .
