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]
^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. Vol. 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.
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Estradiolbenzoatecyclooctenylether (EBCO), or estradiol 3-benzoate 17β-cyclooctenylether, is a synthetic estrogen as well as estrogen ester and ether...
Estradiolbenzoate (EB), sold under the brand name Progynon-B among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms...
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This is a list of currently marketed formulations of estradiolbenzoate (EB) throughout the world. Both EB alone and combinations of EB with other medications...
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Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive...
Estradiolbenzoate butyrate (EBB), sold under the brand names Neolutin N, Redimen, Soluna, and Unijab and formerly known under the developmental code name...
Instead, other non-oral forms of estradiol such as transdermal estradiol are recommended and may be used. Estradiol injectables are generally well-tolerated...
other menopausal symptoms. Along with estradiol valerate, estradiol cypionate, and estradiolbenzoate, estradiol undecylate has been used as an intramuscular...
contraceptive. Along with estradiol valerate, estradiol undecylate, and estradiolbenzoate, estradiol cypionate is used as a form of high-dose estrogen...
be marketed was estradiolbenzoate in 1933, which was followed by many more. One of the most widely used estradiol esters is estradiol valerate, which...
and with parenteral estrogens such as estradiolbenzoate, estradiol valerate, estradiol cypionate, and estradiol undecylate. Progestogens, such as hydroxyprogesterone...
considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiolbenzoate and estradiol cypionate. Esterification aims at either...
medical use. Examples include estriol glucuronide (Emmenin, Progynon), estradiolbenzoate, conjugated estrogens (Premarin), diethylstilbestrol, and ethinylestradiol...
estrogen receptor, the biological target of estrogens like estradiol. Compared to estradiol, certain estrogens in CEEs are more resistant to metabolism...
Estradiol disulfate (also known as E2DS or estradiol 3,17β-disulfate) is an endogenous estrogen conjugate and metabolite of estradiol. It is related to...
esters to be used. Along with estradiolbenzoate, estradiol dipropionate was among the most widely used esters of estradiol for many years following its...
It was used in France. The medication should not be confused with estradiolbenzoate (EB), which has been marketed under similar brand names including...
include estradiol valerate, estradiol cypionate, estradiol enantate, estradiolbenzoate butyrate, and estradiol, while progestins that are used include norethisterone...
suppress lactation in women. It was formulated in combination with estradiolbenzoate (EB), a short-acting estrogen, and testosterone enanthate benzilic...
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ester of estradiol. Estradiolbenzoate has also been marketed under the brand name Di-Folliculine, and should not be confused with estradiol furoate....
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