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| Clinical data | |
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| Drug class | Nonsteroidal antiandrogen |
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| Chemical and physical data | |
| Formula | C15H14F3N3O2S |
| Molar mass | 357.35 g·mol−1 |
| 3D model (JSmol) | |
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RU-57073 is a nonsteroidal antiandrogen which was never marketed. [1] [2] [3] It shows 163% of the affinity of testosterone for the androgen receptor and negligible affinity for other steroid hormone receptors. [1] [2]
Antiandrogens, also known as androgen antagonists or testosterone blockers, are a class of drugs that prevent androgens like testosterone and dihydrotestosterone (DHT) from mediating their biological effects in the body. They act by blocking the androgen receptor (AR) and/or inhibiting or suppressing androgen production. They can be thought of as the functional opposites of AR agonists, for instance androgens and anabolic steroids (AAS) like testosterone, DHT, and nandrolone and selective androgen receptor modulators (SARMs) like enobosarm. Antiandrogens are one of three types of sex hormone antagonists, the others being antiestrogens and antiprogestogens.
Nilutamide, sold under the brand names Nilandron and Anandron, is a nonsteroidal antiandrogen (NSAA) which is used in the treatment of prostate cancer. It has also been studied as a component of feminizing hormone therapy for transgender women and to treat acne and seborrhea in women. It is taken by mouth.
Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.
This article is about the discovery and development of antiandrogens, or androgen receptor (AR) antagonists.
RU-58642 is a nonsteroidal antiandrogen (NSAA) derived from nilutamide with very high affinity and selectivity for the androgen receptor (AR), which made it among the most potent and efficacious antiandrogens known at the time of its discovery. It was investigated for topical application for the treatment of androgenetic alopecia, but development did not proceed past initial trial stages, and it is now only used for scientific research into the AR.
Benorterone, also known by its developmental code name SKF-7690 and as 17α-methyl-B-nortestosterone, is a steroidal antiandrogen which was studied for potential medical use but was never marketed. It was the first known antiandrogen to be studied in humans. It is taken by mouth or by application to skin.
Hydroxyflutamide (HF, OHF) (developmental code name SCH-16423), or 2-hydroxyflutamide, is a nonsteroidal antiandrogen (NSAA) and the major active metabolite of flutamide, which is considered to be a prodrug of hydroxyflutamide as the active form. It has been reported to possess an IC50 of 700 nM for the androgen receptor (AR), which is about 4-fold less than that of bicalutamide.
Oxendolone, sold under the brand names Prostetin and Roxenone, is an antiandrogen and progestin medication which is used in Japan in the treatment of enlarged prostate. However, this use is controversial due to concerns about its clinical efficacy. Oxendolone is not effective by mouth and must be given by injection into muscle.
RU-58841, also known as PSK-3841 or HMR-3841, is a nonsteroidal antiandrogen (NSAA) which was initially developed in the 1980s by Roussel Uclaf, the French pharmaceutical company from which it received its name. It was formerly under investigation by ProStrakan for potential use as a topical treatment for androgen-dependent conditions including acne, pattern hair loss, and excessive hair growth. The compound is similar in structure to the NSAA RU-58642 but contains a different side-chain. These compounds are similar in chemical structure to nilutamide, which is related to flutamide, bicalutamide, and enzalutamide, all of which are NSAAs similarly. RU-58841 can be synthesized either by building the hydantoin moiety or by aryl coupling to 5,5-dimethylhydantoin.
A nonsteroidal antiandrogen (NSAA) is an antiandrogen with a nonsteroidal chemical structure. They are typically selective and full or silent antagonists of the androgen receptor (AR) and act by directly blocking the effects of androgens like testosterone and dihydrotestosterone (DHT). NSAAs are used in the treatment of androgen-dependent conditions in men and women. They are the converse of steroidal antiandrogens (SAAs), which are antiandrogens that are steroids and are structurally related to testosterone.
Topilutamide, known more commonly as fluridil and sold under the brand name Eucapil, is an antiandrogen medication which is used in the treatment of pattern hair loss in men and women. It is used as a topical medication and is applied to the scalp. Topilutamide belongs to a class of molecules known as perfluoroacylamido-arylpropanamides.
Inocoterone acetate (USAN) is a steroid-like nonsteroidal antiandrogen (NSAA) that was developed for topical administration to treat acne but was never marketed. It is the acetate ester of inocoterone, which is less potent in comparison. Inocoterone acetate is actually not a silent antagonist of the androgen receptor but rather a weak partial agonist, similarly to steroidal antiandrogens like cyproterone acetate.
BOMT, also known by its developmental code name Ro 7-2340 and as 6α-bromo-4-oxa-17α-methyl-5α-dihydrotestosterone, is a synthetic steroidal antiandrogen which was first developed in 1970 and was never marketed for medical use. It is the 6α-brominated, 4-oxygenated, and 17α-methylated derivative of the androgen dihydrotestosterone (DHT). Along with benorterone, cyproterone, and flutamide, BOMT was among the earliest antiandrogens to be developed and extensively studied, although it is less well-documented in comparison to the others. BOMT has been investigated clinically in the treatment of benign prostatic hyperplasia, though development for this use did not continue. There was also interest in BOMT for the potential applications of acne, pattern hair loss, and possibly prostate cancer, but it was not developed for these indications either.
DIMP, or N-(3,5-dimethyl-4-isoxazolylmethyl)phthalimide, is a nonsteroidal antiandrogen (NSAA) structurally related to thalidomide that was first described in 1973 and was never marketed. Along with flutamide, it was one of the earliest NSAAs to be discovered, and for this reason, has been described as a "classical" NSAA. The drug is a selective, competitive, silent antagonist of the AR, although it is described as an "only relatively weak competitor". Its relative binding affinity for the androgen receptor is about 2.6% of that of metribolone. DIMP possesses no androgenic, estrogenic, progestogenic, or antigonadotropic activity, but it does reverse the antigonadotropic effects of testosterone, indicating that, like other pure AR antagonists, it is progonadotropic.
Trimethyltrienolone (TMT), also known by its developmental code name R-2956 or RU-2956, is an antiandrogen medication which was never introduced for medical use but has been used in scientific research.
RU-59063 is a nonsteroidal androgen or selective androgen receptor modulator (SARM) which was first described in 1994 and was never marketed. It was originally thought to be a potent antiandrogen, but subsequent research found that it actually possesses dose-dependent androgenic activity, albeit with lower efficacy than dihydrotestosterone (DHT). The drug is an N-substituted arylthiohydantoin and was derived from the first-generation nonsteroidal antiandrogen (NSAA) nilutamide. The second-generation NSAAs enzalutamide, RD-162, and apalutamide were derived from RU-59063.
EM-5854 is a steroidal antiandrogen which was under development by Endoceutics, Inc. for the treatment of prostate cancer. It was first described in a patent in 2008, and was further characterized in 2012. EM-5854 reached phase I/II clinical trials for the treatment of prostate cancer but development was discontinued in March 2019.
5α-Dihydroethisterone is an active metabolite of the formerly clinically used but now-discontinued progestin ethisterone and the experimental and never-marketed hormonal antineoplastic agent ethynylandrostanediol (HE-3235). Its formation from its parent drugs is catalyzed by 5α-reductase in tissues that express the enzyme in high amounts like the liver, skin, hair follicles, and prostate gland. 5α-DHET has significant affinity for steroid hormone receptors and may contribute importantly to the activities of its parent drugs.
RU-56187 is a nonsteroidal antiandrogen which was never marketed. It shows 92% of the affinity of testosterone for the androgen receptor and negligible affinity for other steroid hormone receptors. The medication is a silent antagonist of the androgen receptor. RU-56187 is 3- to 10-fold more potent as an antiandrogen than bicalutamide or nilutamide in animals. Both RU-56187 and RU-58841 appear to be prodrugs of cyanonilutamide (RU-56279) in vivo in animals.
Cyanonilutamide is a nonsteroidal antiandrogen which was never marketed. Both RU-56187 and RU-58841 appear to be prodrugs of cyanonilutamide in vivo in animals. It has relatively low affinity for the androgen receptor but nonetheless shows significant antiandrogenic activity in animals.
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