Estradiol benzoate cyclooctenyl ether
Estradiol benzoate cyclooctenyl ether (EBCO), or estradiol 3-benzoate 17β-cyclooctenyl ether, is a synthetic estrogen as well as estrogen ester and ether – specifically, the C3 benzoate ester and C17β cyclooctenyl ether of estradiol – which was described in the early 1970s and was never marketed.[1][2][3][4] It has been found to have a dramatically prolonged duration of action with oral administration in animals, similarly to the related compound quinestrol (the 3-cyclopentyl ether of ethinylestradiol).[1][5][6] A single oral dose of EBCO sustained high uterus weights for 3 weeks in rats.[1] This long-lasting activity may be due to storage of EBCO in fat.[1] It appears that EBCO is absorbed satisfactorily from the gastrointestinal tract, at least partially survives first-pass metabolism in the liver and intestines, and is then sequestered into fat, from which it is slowly released and activated into estradiol.[1] In contrast to quinestrol, the oral activity of EBCO is greatly improved when it is delivered in an oil solution as opposed to an aqueous vehicle.[1]
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| Other names | EBCO; Estradiol 3-benzoate 17β-cyclooctenyl ether |
| Routes of administration | By mouth[1] |
| Drug class | Estrogen; Estrogen ester; Estrogen ether |
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| Chemical and physical data | |
| Formula | C33H40O3 |
| Molar mass | 484.680 g·mol−1 |
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References
- Falconi G, Galletti F, Celasco G, Gardi R (November 1972). "Oral long-lasting estrogenic activity of estradiol 3-benzoate 17-cyclooctenyl ether". Steroids. 20 (5): 627–38. doi:10.1016/0039-128X(72)90020-7. PMID 4654978.
- Galletti F, Gardi R (April 1974). "Effect of two orally active estradiol derivatives on sulfobromphthalein retention in rats". Pharmacol Res Commun. 6 (2): 135–45. doi:10.1016/s0031-6989(74)80021-4. PMID 4438394.
- Wermuth, Camille G. (2008). "Designing Prodrugs and Bioprecursors". The Practice of Medicinal Chemistry. pp. 721–746. doi:10.1016/B978-0-12-374194-3.00036-6. ISBN 9780123741943.
- Stella, V. (1975). "Pro-drugs: An Overview and Definition". Pro-drugs as Novel Drug Delivery Systems. ACS Symposium Series. 14. pp. 1–115. doi:10.1021/bk-1975-0014.ch001. ISBN 0-8412-0291-5. ISSN 1947-5918.
- Epstein JA (1967). "Prolonged menstrual response of patients with gonadal failure following quinestrol administration". Int. J. Fertil. 12 (2): 181–6. PMID 6033895.
- Giannina T, Meli A (April 1969). "Prolonged oestrogenic activity in rats after single oral administration of ethinyloestradiol-3-cyclopentyl ether". J. Pharm. Pharmacol. 21 (4): 271–2. doi:10.1111/j.2042-7158.1969.tb08247.x. PMID 4390151. S2CID 19407816.