Estradiol hexahydrobenzoate
Chemical compound From Wikipedia, the free encyclopedia
Estradiol hexahydrobenzoate (EHHB), sold under a number of brand names including Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, and Tardoginestryl, is an estrogen medication which was previously used for indications such as menopausal hormone therapy and gynecological disorders.[1][2][3][4][5] EHHB is given by injection into muscle at regular intervals, for instance once every few weeks.[3][5][6][7]
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| Trade names | Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, Tardoginestryl |
| Other names | EHHB; Estradiol cyclohexanecarboxylate; ECHC; Oestradiol hexahydrobenzoate; Estradiol 17β-hexahydrobenzoate; Estradiol 17β-cyclohexanecarboxylate; Estradiol hexabenzoate |
| Routes of administration | Intramuscular injection |
| Drug class | Estrogen; Estrogen ester |
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| ECHA InfoCard | 100.035.623 |
| Chemical and physical data | |
| Formula | C25H34O3 |
| Molar mass | 382.544 g·mol−1 |
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Side effects of EHHB include breast tenderness, breast enlargement, nausea, headache, and fluid retention.[8] EHHB is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[9][10] It is an estrogen ester and a prodrug of estradiol in the body.[10][9] Because of this, it is considered to be a natural and bioidentical form of estrogen.[10]
EHHB was first described in 1956,[11][12] and was introduced for medical use by 1957.[6] It was used in France.[6] The medication should not be confused with estradiol benzoate (EB), which has been marketed under similar brand names including Benzo-Ginestryl, Benzo-Ginoestril, and Benzo-Gynoestryl.[3][6][13]
Medical uses
EHHB was marketed in France in a 5 mg/mL oil solution in ampoules for intramuscular injection at regular intervals, for instance once every few weeks.[3][5][6][7] Use of EHHB for feminizing hormone therapy in transgender women has been reported.[14] A combination of 3 mg EHHB, 75 mg hydroxyprogesterone caproate, and 100 mg testosterone hexahydrobenzoate in 2 mL oil solution provided in ampoules has been marketed under the brand name Trinestril AP in Brazil.[15][16][17] Its indications include menopausal hormone therapy and the treatment of functional uterine bleeding.[15] The combination is administered typically once per month by intramuscular injection.[15]
Pharmacology
Pharmacodynamics
EHHB is an estradiol ester, or a prodrug of estradiol.[10][9][18] As such, it is an estrogen, or an agonist of the estrogen receptors.[10][9] EHHB is of about 40% higher molecular weight than estradiol due to the presence of its C17β cyclohexanecarboxylate ester.[1] Because EHHB is a prodrug of estradiol, it is considered to be a natural and bioidentical form of estrogen.[10]
Pharmacokinetics
A combination of EHHB and norgestrel as a combined injectable contraceptive reportedly has a duration of action of about 3 weeks.[19]
Chemistry
EHHB, also known as estradiol cyclohexanecarboxylate (ECHC) as well as estradiol 17β-hexahydrobenzoate or estradiol 17β-cyclohexanecarboxylate, is a synthetic estrane steroid and an estrogen ester.[1][2][3][4] It is specifically the C17β cyclohexanecarboxylate (hexahydrobenzoate) ester of estradiol.[1][2]
History
EHHB was first described and characterized in 1956.[11][12] It was developed in France.[11][12] The medication was introduced for medical use in France by 1957.[6] A publicized case report of a rapidly growing breast cancer tumor in a 53-year-old woman 10 days after initiation of therapy with 5 mg/month EHHB by intramuscular injection for hot flashes was published in 1962.[20][21][22] The woman died due to breast cancer 10 months after the diagnosis.[20][22]
Society and culture
Generic names
Estradiol hexahydrobenzoate is the generic name of the drug and its INN), while oestradiol hexahydrobenzoate is its BANM.[1][2][3][4] The medication is also known as estradiol cyclohexanecarboxylate (ECHC).[1][2][3][4]
Brand names
EHHB has been marketed under the brand names Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, and Tardoginestryl.[1][2][3][4][5]
Availability
Research
A combination of 5 mg EHHB in peanut oil solution and 25 mg norgestrel in aqueous suspension as a once-monthly combined injectable contraceptive was studied, but this formulation was ultimately never marketed.[23][24][25][26][27][19]
References
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