|Chemical and physical data
|3D model (JSmol)
Tigestol (INN, USAN), also known as 17α-ethynylestr-5(10)-en-17β-ol,is a steroidal progestin of the 19-nortestosterone group that was developed by Organon in the 1960s but was never marketed. It is an isomer of the related 19-nortestosterone derivative progestins lynestrenol and cingestol.
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.
Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.
Etynodiol diacetate, or ethynodiol diacetate, sold under the brand names Demulen and Femulen among others, is a progestin medication which is used in birth control pills. The medication is available only in combination with an estrogen. It is taken by mouth.
Etynodiol, or ethynodiol, is a steroidal progestin of the 19-nortestosterone group which was never marketed. A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive. Etynodiol is sometimes used as a synonym for etynodiol diacetate.
Norgestrienone, sold under the brand names Ogyline, Planor, and Miniplanor, is a progestin medication which has been used in birth control pills, sometimes in combination with ethinylestradiol. It was developed by Roussel Uclaf and has been registered for use only in France. Under the brand name Planor, it has been marketed in France as 2 mg norgestrienone and 50 μg ethinylestradiol tablets. It is taken by mouth.
Lynestrenol, sold under the brand names Exluton and Ministat among others, is a progestin medication which is used in birth control pills and in the treatment of gynecological disorders. The medication is available both alone and in combination with an estrogen. It is taken by mouth.
Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.
Mibolerone, also known as dimethylnortestosterone (DMNT) and sold under the brand names Cheque Drops and Matenon, is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was marketed by Upjohn for use as a veterinary drug. It was indicated specifically as an oral treatment for prevention of estrus (heat) in adult female dogs.
Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.
Altrenogest, sold under the brand names Swinemate and Altren manufactured by Aurora Pharmaceutical and Regumate manufactured by Merck, is a progestin of the 19-nortestosterone group which is widely used in veterinary medicine to suppress or synchronize estrus in horses and pigs. It is available for veterinary use in both Europe and the United States.
Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed. It was available both alone and in combination with an estrogen. The medication is taken by mouth.
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.
Zanoterone, also known as (5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol, is a steroidal antiandrogen which was never marketed. It was investigated for the treatment of benign prostatic hyperplasia (BPH) but failed to demonstrate sufficient efficacy in phase II clinical trials, and also showed an unacceptable incidence rate and severity of side effects. As such, it was not further developed.
Ethynerone, also known as 17α-(2-chloroethynyl)estra-4,9-dien-17β-ol-3-one, is a steroidal progestin of the 19-nortestosterone group that was first reported in 1961 but was never marketed. Under the developmental code name MK-665, it was studied in combination with mestranol as an oral contraceptive. Development of the drug was discontinued due to concerns surrounding toxicity findings in dogs. It is a chloroethynylated derivative of norethisterone.
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.
Cingestol, also known as 17α-ethynylestr-5-en-17β-ol, is a steroidal progestin of the 19-nortestosterone group that was never marketed. It was synthesized in 1969 and was developed in the 1970s by Organon as a low-dose, progestogen-only contraceptive, but in 1984, was still described as "under investigation". The drug is an isomer of lynestrenol with the double bond between C5 and C6.
Tosagestin, also known as 11-methylene-δ15-norethisterone or 17α-ethynyl-11-methylene-19-nor-δ15-testosterone, is a progestin of the 19-nortestosterone group which was under development by Organon in the United States and Europe as a hormonal contraceptive and for the treatment of menopausal symptoms but was never marketed.
Clomegestone acetate (USAN), or clomagestone acetate, also known as 6-chloro-17α-acetoxy-16α-methylpregna-4,6-diene-3,20-dione, is a steroidal progestin of the 17α-hydroxyprogesterone group which was developed as an oral contraceptive but was never marketed. It is the acetate ester of clomegestone, which, similarly to clomegestone acetate, was never marketed. Clomegestone acetate is also the 17-desoxy cogener of clometherone, and is somewhat more potent in comparison. Similarly to cyproterone acetate, clomegestone acetate has been found to alter insulin receptor concentrations in adipose tissue, and this may indicate the presence of glucocorticoid activity.
Allyltestosterone, or 17α-allyltestosterone, also known as 17α-allylandrost-4-en-17β-ol-3-one, is a steroid derived from testosterone that was first synthesized in 1936 and was never marketed. Along with propyltestosterone (topterone), it has been patented as a topical antiandrogen and hair growth inhibitor. Allyltestosterone is the parent structure of two marketed 19-nortestosterone progestins, allylestrenol and altrenogest. These progestins are unique among testosterone derivatives in that they appear to be associated with few or no androgenic effects.
Ticabesone is a synthetic glucocorticoid corticosteroid which was never marketed.