|Trade names||Depostat, Primostat|
|Synonyms||SH-582; SH-80582; NSC-84054; Gestonorone hexanoate; Gestronol hexanoate; Gestronol caproate; Norhydroxy-progesterone caproate; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione hexanoate; 17α-Hydroxy-19-norprogesterone hexanoate|
|Drug class||Progestin; Progestogen; Progestogen ester; Antigonadotropin|
|Chemical and physical data|
|Molar mass||414.578 g/mol|
|3D model (JSmol)|
Gestonorone caproate, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a progestin medication which is used in the treatment of enlarged prostate and endometrial cancer. It is not effective by mouth and must be given by injection into muscle, typically once a week.
Side effects of gestonorone caproate are similar to those of other progestins. Gestonorone caproate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has no other important hormonal activity.
Gestonorone caproate was discovered in 1960 and was introduced for medical use by 1973. It has been used widely throughout Europe, including in the United Kingdom, and has also been marketed in certain other countries such as Japan, China, and Mexico. However, it has since mostly been discontinued, and it remains available today only in a handful of countries, including the Czech Republic, Japan, Mexico, and Russia.
Gestonorone caproate is a strong, long-acting, and pure progestogen, possessing no androgenic, anabolic, antiandrogenic, estrogenic, antiestrogenic, corticosteroid, or teratogenic effects. In animals, it is approximately 25 times more potent than progesterone or hydroxyprogesterone caproate. In humans, 100 or 200 mg intramuscular gestonorone caproate has been said to be equivalent to 1,000 mg intramuscular hydroxyprogesterone caproate.
Like other potent progestins, gestonorone caproate possesses potent antigonadotropic activity and is capable of markedly suppressing the gonadal production and circulating levels of sex hormones such as testosterone and estradiol. A clinical study found that 400 mg/week intramuscular gestonorone caproate suppressed testosterone levels by 75% in men, while orchiectomy as a comparator reduced testosterone levels by 91%. Levels of luteinizing hormone, conversely, remained unchanged.
Like the closely related progestins hydroxyprogesterone caproate and 19-norprogesterone, gestonorone caproate shows poor activity orally and must be administered parenterally; specifically, via intramuscular injection. Gestonorone caproate is administered once weekly by intramuscular injection, via which it acts as a depot.
Gestonorone caproate, also known as norhydroxyprogesterone caproate, 17α-hydroxy-19-norprogesterone 17α-hexanoate, or 17α-hydroxy-19-norpregn-4-ene-3,20-dione 17α-hexanoate, is a synthetic norpregnane steroid and a derivative of progesterone. It is specifically a combined derivative of 17α-hydroxyprogesterone and 19-norprogesterone, or of gestronol (17α-hydroxy-19-norprogesterone), with a hexanoate (caproate) ester at the C17α position. Analogues and derivatives of gestonorone caproate include algestone acetophenide (dihydroxyprogesterone acetophenide), demegestone, hydroxyprogesterone caproate, nomegestrol acetate, norgestomet, and segesterone acetate (nestorone, elcometrine), as well as 18-methylsegesterone acetate.
Society and culture
Gestonorone caproate has been available widely in Europe, including in the United Kingdom, and has also been marketed in Japan, China, Mexico, and certain other countries. However, it has been discontinued in most countries and its availability is more limited today; it appears to remain marketed only in the Czech Republic, Japan, Mexico, and Russia. It has not been marketed in the United States, Canada, and many other countries.
SH-834 was a combination of 90 mg estradiol valerate and 300 mg gestonorone caproate for weekly intramuscular injection that was developed by Schering in the 1970s. It was investigated clinically as a treatment for breast cancer and was found to be effective, but does not seem to have been marketed.
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The preparations used were Proluton Depot (17a-hydroxy-progesterone caproate) and in 3 patients SH 5132 (17a-hydroxy-19-norprogesterone caproate); 100 mg of the latter corresponds to 1000 mg of Proluton Depot.
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Thirteen patients with primary adenocarcinoma of the uterine corpus were treated for 21 days with l7alphahydroxy-progesterone-caproate (Primolut Depot@, Schering), 1000 mg daily, or 17alpha-hydroxy-19-nor-progesterone-caproate (DepostatB, Schering), 200 mg daily. These doses can be considered as equivalent.
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Another synthetic gestogen, 17-hydroxy-19-norprogesterone caproate (Depostat-Schering), 400 mg by i.m. weekly injections suppressed T levels to 25% of pretreatment values (Sander er al., 1978).
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Gestonorone caproate, another progestational agent, was investigated at our institution. Eighteen patients with painful metastatic [prostate cancer] with objective relapse after orchiectomy were treated with 400 mg/week i.m.
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Gestonorone [caproate] 100 or 200 mg/week i.m.
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A study was carried out in 30 male patients with benign prostate hyperplasia to assess the effectiveness of treatment with a progestational agent, gestonorone caproate (200 mg), given intramuscularly every 7 days over a period of 2 to 3 months.
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