Английская Википедия:Estradiol hexahydrobenzoate
Шаблон:Short description Шаблон:Distinguish Шаблон:Drugbox 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]
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 Шаблон:Abbrlink), while oestradiol hexahydrobenzoate is its Шаблон:Abbrlink.[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
EHHB was previously marketed in France.[6]
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
Шаблон:Estradiol Шаблон:Estrogens and antiestrogens Шаблон:Estrogen receptor modulators
- ↑ 1,0 1,1 1,2 1,3 1,4 1,5 1,6 Шаблон:Cite book
- ↑ 2,0 2,1 2,2 2,3 2,4 2,5 Шаблон:Cite book
- ↑ 3,0 3,1 3,2 3,3 3,4 3,5 3,6 3,7 Шаблон:Cite book
- ↑ 4,0 4,1 4,2 4,3 4,4 Шаблон:Cite book
- ↑ 5,0 5,1 5,2 5,3 Шаблон:Cite book
- ↑ 6,0 6,1 6,2 6,3 6,4 6,5 6,6 Шаблон:Cite book
- ↑ 7,0 7,1 Шаблон:Cite book
- ↑ Шаблон:Cite book
- ↑ 9,0 9,1 9,2 9,3 Шаблон:Cite journal
- ↑ 10,0 10,1 10,2 10,3 10,4 10,5 Шаблон:Cite book
- ↑ 11,0 11,1 11,2 Шаблон:Cite journal
- ↑ 12,0 12,1 12,2 Шаблон:Cite journal
- ↑ Шаблон:Cite book
- ↑ Шаблон:Cite book
- ↑ 15,0 15,1 15,2 Шаблон:Cite web
- ↑ Шаблон:Cite book
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite book
- ↑ 19,0 19,1 Шаблон:Cite book
- ↑ 20,0 20,1 Шаблон:Cite journal
- ↑ Шаблон:Cite book
- ↑ 22,0 22,1 Шаблон:Cite book
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite book
- ↑ Шаблон:Cite journal
