Gestadienol acetate (developmental code name CIBA-31458-Ba or CIBA-31458) an orally active progestin which was described in the literature in 1967 and was never marketed.Gupta, A. (1967, January). Effect of the new progestogen, CIBA 31458 on the human endometrium. In Journal of Reproduction and Fertility (Vol. 14, No. 3, p. 530). 22 Newmarket Rd, Cambridge CB5 8DT, England: Journal of Reproduction and Fertility LTD. http://www.reproduction-online.org/content/14/3/523.full.pdf It has no

androgen An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This in ...

ic or

estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...

ic effects. The effects of gestadienol acetate on the endometrium and its general pharmacology were studied in a

clinical trial Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, diet ...

in women. It has also been studied in a clinical trial for

benign prostatic hyperplasia Benign prostatic hyperplasia (BPH), also called prostate enlargement, is a noncancerous increase in size of the prostate gland. Symptoms may include frequent urination, trouble starting to urinate, weak stream, inability to urinate, or loss o ...

in men, but was ineffective.

Chemistry

Gestadienol acetate, also known as norhydroxy-δ⁶-progesterone acetate, 6-dehydro-17α-hydroxy-19-norprogesterone 17α-acetate, or 17α-hydroxy-19-norpregn-4,6-diene-3,20-dione 17α-acetate, is a synthetic norpregnane steroid and a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

of progesterone. It is specifically a combined derivative of

17α-hydroxyprogesterone 17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many o ...

and 19-norprogesterone, or of gestronol (17α-hydroxy-19-norprogesterone), with an acetate

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

at the C17α position and a

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...

between the C6 and C7 positions. Gestadienol acetate is the C17α acetate

of gestadienol. Analogues of gestadienol acetate include

algestone acetophenide Algestone acetophenide, also known more commonly as dihydroxyprogesterone acetophenide (DHPA) and sold under the brand names Perlutal and Topasel among others, is a progestin medication which is used in combination with an estrogen as a form of ...

(dihydroxyprogesterone acetophenide), demegestone,

gestonorone caproate 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 cancer of the en ...

(norhydroxyprogesterone caproate), hydroxyprogesterone acetate,

hydroxyprogesterone caproate Hydroxyprogesterone caproate (OHPC), sold under the brand names Proluton and Makena among others, is a progestin medication which is used to prevent preterm birth in pregnant women with a history of the condition and to treat gynecological diso ...

nomegestrol acetate Nomegestrol acetate (NOMAC), sold under the brand names Lutenyl and Zoely among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders.http://www.ema. ...

, norgestomet, and

segesterone acetate Segesterone acetate (SGA), sold under the brand names Nestorone, Elcometrine, and Annovera, is a progestin medication which is used in birth control and in the treatment of endometriosis in the United States, Brazil, and other South American coun ...

(nestorone).

References

Abandoned drugs Acetate esters Enones Norpregnanes Progestogen esters Progestogens {{Steroid-stub