Gestadienol acetate

Last updated
Gestadienol acetate
Gestadienol acetate.svg
Clinical data
Other namesCIBA-31458-Ba; CIBA-31458; Norhydroxy-δ6-progesterone acetate; 6-Dehydro-17α-acetoxy-19-norprogesterone; 17α-Acetoxy-19-norpregn-4,6-diene-3,20-dione
Routes of
administration
By mouth [1] [2]
Drug class Progestogen; Progestogen ester
Identifiers
CAS Number
PubChem CID
ECHA InfoCard 100.224.529 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H28O4
Molar mass 356.462 g·mol−1
3D model (JSmol)

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. [3] [1] [2] [4] [5] It has no androgenic or estrogenic effects. [6] The effects of gestadienol acetate on the endometrium and its general pharmacology were studied in a clinical trial in women. [2] [5] It has also been studied in a clinical trial for benign prostatic hyperplasia in men, but was ineffective. [6]

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 of progesterone. [3] It is specifically a combined derivative of 17α-hydroxyprogesterone and 19-norprogesterone, or of gestronol (17α-hydroxy-19-norprogesterone), with an acetate ester at the C17α position and a double bond between the C6 and C7 positions. [3] Gestadienol acetate is the C17α acetate ester of gestadienol. [3] Analogues of gestadienol acetate include algestone acetophenide (dihydroxyprogesterone acetophenide), demegestone, gestonorone caproate (norhydroxyprogesterone caproate), hydroxyprogesterone acetate, hydroxyprogesterone caproate, nomegestrol acetate, norgestomet, and segesterone acetate (nestorone). [3]

Related Research Articles

17α-Hydroxyprogesterone chemical compound

17α-Hydroxyprogesterone (17α-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids.

Gestonorone caproate chemical compound

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 endometrium. It is given by injection into muscle typically once a week.

Hydroxyprogesterone caproate chemical compound

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 disorders. It has also been formulated in combination with estrogens for various indications and as a form of long-lasting injectable birth control. It is not used by mouth and is instead given by injection into muscle or fat, typically once per week to once per month depending on the indication.

Combined injectable contraceptives (CICs) are a form of hormonal birth control for women. They consist of monthly injections of combined formulations containing an estrogen and a progestin to prevent pregnancy.

Chlormadinone acetate chemical compound

Chlormadinone acetate (CMA), sold under the brand names Belara, Gynorelle, Lutéran, and Prostal among others, is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy, as a component of menopausal hormone therapy, in the treatment of gynecological disorders, and in the treatment of androgen-dependent conditions like enlarged prostate and prostate cancer in men and acne and hirsutism in women. It is available both at a low dose in combination with an estrogen in birth control pills and, in a few countries like France and Japan, at low, moderate, and high doses alone for various indications. It is taken by mouth.

Melengestrol acetate chemical compound

Melengestrol acetate (MLGA), sold under the brand names Heifermax and MGA among others, is a progestin medication which is used in animal reproduction. It is not approved for use in humans, and is instead used as an implantable contraceptive for captive animals in zoos and other refuges, and is also used as a feed additive to promote growth in cattle, a purpose it is licensed for in the United States and Canada.

Medrogestone chemical compound

Medrogestone, sold under the brand name Colprone among others, is a progestin medication which has been used in menopausal hormone therapy and in the treatment of gynecological disorders. It is available both alone and in combination with an estrogen. It is taken by mouth.

Delmadinone acetate chemical compound

Delmadinone acetate (DMA), sold under the brand name Tardak among others, is a progestin and antiandrogen which is used in veterinary medicine to treat androgen-dependent conditions such as benign prostatic hyperplasia. It must be used with care as it has the potential to cause adrenal insufficiency via inhibition of adrenocorticotropic hormone (ACTH) secretion from the pituitary gland. DMA is the C17α acetate ester of delmadinone, which, in contrast to DMA, was never marketed for medical use.

Segesterone acetate chemical compound

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 countries. It is available both alone and in combination with an estrogen. It is not effective by mouth and must be given by other routes, most typically as a vaginal ring or implant that is placed into fat.

19-Norprogesterone chemical compound

19-Norprogesterone, also known as 19-norpregn-4-ene-3,20-dione, is a steroidal progestin and close analogue of the sex hormone progesterone, lacking only the C19 methyl group of that molecule. It was first synthesized in 1944 in the form of a mixture that also included unnatural stereoisomers of progesterone, and this mixture was found to be at least equivalent to progesterone in terms of progestogenic activity. Subsequent investigations revealed that 17-isoprogesterone and 14-iso-17-isoprogesterone are devoid of progestogenic activity. 19-Norprogesterone was resynthesized in 1951 with an improved method, and was confirmed to be the component of the mixture synthesized in 1944 that was responsible for its progestogenic activity. In 1953, a paper was published showing that 19-norprogesterone possessed 4- to 8-fold the activity of progesterone in the Clauberg assay in rabbits, and at the time of this discovery, 19-norprogesterone was the most potent progestogen known.

Hydroxyprogesterone acetate chemical compound

Hydroxyprogesterone acetate (OHPA), sold under the brand name Prodox, is an orally active progestin related to hydroxyprogesterone caproate (OHPC) which has been used in clinical and veterinary medicine. It has reportedly also been used in birth control pills.

Hydroxyprogesterone heptanoate chemical compound

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.

Progestogen ester drug class

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.

17α-Methylprogesterone chemical compound

17α-Methylprogesterone (17α-MP), or 17α-methylpregn-4-ene-3,20-dione, is a steroidal progestin related to progesterone that was synthesized and characterized in 1949 but was never marketed. Along with ethisterone (1938) and 19-norprogesterone (1951), 17α-MP was one of the earliest derivatives of progesterone to be identified as possessing progestogenic activity. Similarly to progesterone and derivatives like 17α-hydroxyprogesterone and 19-norprogesterone, 17α-MP was found to possess poor oral bioavailability, but showed improved progestogenic activity relative to progesterone when administered via other routes. In addition to its activity as a progestogen, 17α-MP has also been found to possess some antiglucocorticoid activity.

Megestrol caproate chemical compound

Megestrol caproate, abbreviated as MGC, is a progestin medication which was never marketed. It was developed in Russia in 2002. In animals, MGC shows 10-fold higher progestogenic activity compared to progesterone when both are administered via subcutaneous injection. In addition, MGC has no androgenic, anabolic, or estrogenic activity. The medication was suggested as a potential contraceptive and therapeutic agent.

Methenmadinone caproate chemical compound

Methenmadinone caproate is a progestin medication which was developed in Czechoslovakia in the 1960s and was studied for potential use in combined injectable contraceptives in the 1970s but was never marketed. It was studied as a combined injectable contraceptive in combination with estradiol valerate at doses of 60 mg and 10 mg, respectively, once a month by intramuscular injection. MMC is the C17α caproate (hexanoate) ester of methenmadinone and an analogue of methenmadinone acetate. In addition to MMA, analogues of MMC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and megestrol caproate.

16-Methylene-17α-hydroxyprogesterone acetate chemical compound

16-Methylene-17α-hydroxyprogesterone acetate is a progestin of the 17α-hydroxyprogesterone group which was never marketed. Given orally, it shows about 2.5-fold the progestogenic activity of parenteral progesterone in animal bioassays. It is a parent compound of the following clinically used progestins:

Gestonorone acetate chemical compound

Gestonorone acetate, or gestronol acetate, also known as norhydroxyprogesterone acetate, is a progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups which was developed in the early 1960s but was never marketed. It is the C17α acetate ester of gestronol (17α-hydroxy-19-norprogesterone).

References

  1. 1 2 Desaulles, P. A.; Krahenbuhl, C. (1967). "Biological Properties of a New Progesterone Analogue". European Journal of Endocrinology. 56 (1 Suppl): S143. doi:10.1530/acta.0.056S143. ISSN   0804-4643.
  2. 1 2 3 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
  3. 1 2 3 4 5 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 659. ISBN   978-1-4757-2085-3.
  4. Petrow V (1970). "The contraceptive progestagens". Chem. Rev. 70 (6): 713–26. doi:10.1021/cr60268a004. PMID   4098492.
  5. 1 2 Heusler K, Kalvoda J (1996). "Between basic and applied research: Ciba's involvement in steroids in the 1950s and 1960s". Steroids. 61 (8): 492–503. doi:10.1016/0039-128x(96)00040-2. PMID   8870170. S2CID   37228396.
  6. 1 2 Hald T, From A (1972). "Benign prostatic hypertrophy treated with a gestagen. A double-blind clinical trial with randomized allocation". Scand. J. Urol. Nephrol. 6: Suppl 15:157–6. doi:10.3109/00365597209133659. PMID   4118753.