Clinical data | |
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Other names | Estradiol propionicotinate; Estradiol propionate nicotinate; Estradiol nicotinate propionate; Estradiol 17β-nicotinate 3-propionate |
Routes of administration | Intramuscular injection |
Drug class | Estrogen; Estrogen ester |
Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.021.786 |
Chemical and physical data | |
Formula | C27H31NO4 |
Molar mass | 433.539 g/mol g·mol−1 |
3D model (JSmol) | |
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Estrapronicate (INN), also known as estradiol nicotinate propionate is an estrogen medication and estrogen ester which was never marketed. [1] It was studied as a component of the experimental tristeroid combination drug Trophobolene, which contained nandrolone decanoate, estrapronicate, and hydroxyprogesterone heptanoate. [2] [3]
Estradiol benzoate (EB), sold under the brand name Progynon-B among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for transgender women, and in the treatment of gynecological disorders. It is also used in the treatment of prostate cancer in men. Estradiol benzoate is used in veterinary medicine as well. When used clinically, the medication is given by injection into muscle usually two to three times per week.
Estradiol dipropionate (EDP), sold under the brand names Agofollin, Di-Ovocylin, and Progynon DP among others, is an estrogen medication which has been used in hormone therapy for menopausal symptoms and low estrogen levels in women and in the treatment of gynecological disorders. It has also been used in feminizing hormone therapy for transgender women and in the treatment of prostate cancer in men. Although widely used in the past, estradiol dipropionate has largely been discontinued and is mostly no longer available today. It appears to remain in use only in Japan, Macedonia, and Australia. Estradiol dipropionate is given by injection into muscle at intervals ranging from once or twice a week to once every week and a half to two weeks.
Testosterone caproate (TCa), also known as testosterone hexanoate, is an androgen and anabolic steroid and a testosterone ester that is no longer marketed. It was formerly available as a component of Omnadren 250, along with testosterone isocaproate, testosterone phenylpropionate, and testosterone propionate, but this formulation has since been discontinued.
Hydroxyprogesterone heptanoate (OHPH), also known as hydroxyprogesterone enanthate (OHPE) and sold under the brand names H.O.P., Lutogil A.P., and Lutogyl A.P. among others, is a progestin medication used for progestogenic indications. It has been formulated both alone and in together with estrogens, androgens/anabolic steroids, and other progestogens in several combination preparations. OHPH is given by injection into muscle at regular intervals.
Orestrate (INN), also known as estradiol 3-propionate 17β-(1-cyclohexenyl) ether, is an estrogen medication and estrogen ester which was never marketed. It is the C3 propionate ester and C17β-(1-cyclohexenyl) ether of estradiol.
Estradiol diundecylate, or estradiol diundecanoate, also known as 17β-estradiol 3,17β-diundecylate, is an estrogen and an estrogen ester – specifically, the 3,17β-diundecylate ester of estradiol – which has been marketed in Romania. It was described, along with a variety of other estradiol esters such as estradiol undecylate, by Karl Junkmann of Schering AG in 1953.
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. EHHB is given by injection into muscle at regular intervals, for instance once every few weeks.
Atrimustine (INN), also known as bestrabucil or busramustine, is a cytostatic antineoplastic agent which was under development in Japan by Kureha Chemicals for the treatment of breast cancer and non-Hodgkin's lymphoma as well as for the prevention of graft-versus-host disease in bone marrow transplant recipients. It is the benzoate ester of an ester conjugate of estradiol and chlorambucil, which results in targeted/site-directed cytostatic activity toward estrogen receptor-positive tissues such as breast and bone. It reached preregistration for the treatment of cancer but was ultimately discontinued. Estrogenicic side effects of atrimustine in clinical trials included vaginal bleeding and gynecomastia. The drug was first patented in 1980.
A progestogen ester is an ester of a progestogen or progestin. The prototypical progestogen is progesterone, an endogenous sex hormone. Esterification is frequently employed to improve the pharmacokinetics of steroids, including oral bioavailability, lipophilicity, and elimination half-life. In addition, with intramuscular injection, steroid esters are often absorbed more slowly into the body, allowing for less frequent administration. Many steroid esters function as prodrugs.
Testosterone cyclohexylpropionate is an androgen and anabolic steroid and a testosterone ester.
Nandrolone undecanoate, also known as nandrolone undecylate and sold under the brand names Dynabolon, Dynabolin, and Psychobolan, is an androgen and anabolic steroid medication and a nandrolone ester which was developed in the 1960s and was previously marketed in France, Germany, Italy, and Monaco, but has since been discontinued and is now no longer known to be available.
Estradiol 3-propionate, or 3-propanoylestradiol, also known as estra-1,3,5(10)-triene-3,17β-diol 3-propionate, is a semisynthetic, steroidal estrogen that was never marketed. It is an estrogen ester, specifically, a propionic acid ester of estradiol, and acts as a prodrug to it in vivo. The chemical structure of estradiol 3-propionate is contained within estradiol dipropionate, estrapronicate, and orestrate, all of which are also estradiol esters.
Prasterone enanthate, also known as dehydroepiandrosterone enanthate (DHEA-E) and sold in combination with estradiol valerate under the brand name Gynodian Depot among others, is a weak androgen, estrogen, and neurosteroid medication which is used as a component of menopausal hormone therapy to treat menopausal symptoms in women. It is available only as an injectable preparation in combination with estradiol valerate. The medication is given by injection into muscle typically once ever 4 weeks.
Testosterone enantate benzilic acid hydrazone (TEBH), or testosterone 17β-enantate 3-benzilic acid hydrazone, is a synthetic, injected androgen/anabolic steroid and an androgen ester – specifically, the C17β enantate (heptanoate) ester and C3 benzilic acid hydrazone of testosterone. It was previously marketed in combination with estradiol benzoate and estradiol dienantate under the brand names Climacteron, Lactimex, and Lactostat. Clinical studies have assessed this formulation. TEBH was first described in the scientific literature in 1959. It is a very long-lasting prodrug of testosterone when administered in oil via intramuscular injection.
Estramustine is an estrogen and cytostatic antineoplastic agent which was never marketed. It is an estrogen ester – specifically, the C3 normustine ester of estradiol – and acts in part as a prodrug of estradiol in the body. Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and used in the treatment of prostate cancer.
Estradiol dibutyrate (EDBu), or estradiol dibutanoate, is an estrogen medication and an estrogen ester – specifically, a diester of estradiol – which is no longer used. It was a component of Triormon Depositum, a combination formulation of estradiol dibutyrate, testosterone caproate, and hydroxyprogesterone heptanoate which was developed in the 1950s.
Estrapronicate/hydroxyprogesterone heptanoate/nandrolone undecanoate (EPC/OHPH/NU), tentative brand name Trophobolene or Trophoboline, is an injectable combination medication of estrapronicate, an estrogen, hydroxyprogesterone heptanoate (OHPH), a progestogen, and nandrolone undecanoate (NU), an androgen/anabolic steroid, which was never marketed. It contained 1.3 mg EPC, 80 mg OHPH, and 50 mg NU in oil solution and was administered by intramuscular injection. The medication was developed by Théramex in the mid-to-late 1960s. It was studied for use for a variety of indications, including treatment of coronary insufficiency, growth deficiency, and osteoporosis, as well as hormonal disorders in gonadotropin deficiency.
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