Butriptyline, sold under the brand name Evadyne among others, is a tricyclic antidepressant (TCA) that has been used in the United Kingdom and several other European countries for the treatment of depression but appears to no longer be marketed. Along with trimipramine, iprindole, and amoxapine, it has been described as an "atypical" or "second-generation" TCA due to its relatively late introduction and atypical pharmacology. It was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.
Furazabol, also known as androfurazanol, is a synthetic, orally active anabolic-androgenic steroid which has been marketed in Japan since 1969. It is a 17α-alkylated derivative of dihydrotestosterone (DHT) and is closely related structurally to stanozolol, differing from it only by having a furazan ring system instead of pyrazole. Furazabol has a relatively high ratio of anabolic to androgenic activity. As with other 17α-alkylated AAS, it may have a risk of hepatotoxicity. The drug has been described as an antihyperlipidemic and is claimed to be useful in the treatment of atherosclerosis and hypercholesterolemia, but according to William Llewellyn, such properties of furazabol are a myth.
Pheneturide, also known as phenylethylacetylurea, is an anticonvulsant of the ureide class. Conceptually, it can be formed in the body as a metabolic degradation product from [[phenobarbital]]. It is considered to be obsolete, and is now seldom used. It is marketed in Europe, including in Poland, Spain, and the United Kingdom. Pheneturide has a similar profile of anticonvulsant activity and toxicity relative to phenacemide, but is less toxic in comparison, despite still being a toxic drug. As such, it is only used in cases of severe epilepsy when other, less-toxic drugs have failed. Pheneturide inhibits the metabolism and thus increases the levels of other anticonvulsants, such as phenytoin.
Mestranol, sold under the brand names Enovid, Norinyl, and Ortho-Novum among others, is an estrogen medication which has been used in birth control pills, menopausal hormone therapy, and the treatment of menstrual disorders. It is formulated in combination with a progestin and is not available alone. It is taken by mouth.
Hydroxydione, as hydroxydione sodium succinate, also known as 21-Hydroxy-5β-pregnane-3,20-dione, is a neuroactive steroid which was formerly used as a general anesthetic, but was discontinued due to incidence of thrombophlebitis in patients. It was introduced in 1957, and was the first neuroactive steroid general anesthetic to be introduced for clinical use, an event which was shortly preceded by the observation in 1954 of the sedative properties of progesterone in mice.
Carfenazine (INN), or carphenazine (BAN), also known as carphenazine maleate (USAN), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.
Acefluranol, also known as 2,3-bis(3,4-diacetoxy-5-fluorophenyl)pentane, is a nonsteroidal antiestrogen of the stilbestrol group that was never marketed. It is a polyfluorinated biphenyl that is related to polybrominated and polychlorinated biphenyls and diethylstilbestrol.
Progynon was an orally active formulation of estrogen that was developed by Adolf Butenandt at Schering and introduced in Germany in 1928. It was reportedly the first sex hormone product and hence also the first estrogen product to be introduced for medical use. Progynon was originally an ovarian or placental extract, but Schering soon switched for economic reasons to using the urine of women who were in late pregnancy. This form of Progynon was essentially the same product as Emmenin, which was developed by James Collip at Ayerst and introduced in Canada in 1930.
Alentemol (INN), or alentamol, is a selective dopamine autoreceptor agonist described as an antipsychotic, which was never marketed.
Norketamine, or N-desmethylketamine, is the major active metabolite of ketamine, which is formed mainly by CYP3A4. Similarly to ketamine, norketamine acts as a noncompetitive NMDA receptor antagonist, but is about 3–5 times less potent as an anesthetic in comparison. Also, similarly again to ketamine, norketamine binds to the μ- and κ-opioid receptors. Relative to ketamine, norketamine is much more potent as an antagonist of the α7-nicotinic acetylcholine receptor, and produces rapid antidepressant effects in animal models which have been reported to correlate with its activity at this receptor. However, norketamine is about 1/5th as potent as ketamine as an antidepressant in mice as per the forced swim test, and this seems also to be in accordance with its 3–5-fold reduced comparative potency in vivo as an NMDA receptor antagonist. Norketamine is metabolized into dehydronorketamine and hydroxynorketamine, which are far less or negligibly active as NMDA receptor antagonists in comparison, but retain activity as potent antagonists of the α7-nicotinic acetylcholine receptor.
Doisynolic acid is a synthetic, nonsteroidal, orally active estrogen that was never marketed. The reaction of estradiol or estrone with potassium hydroxide, a strong base, results in doisynolic acid as a degradation product, which retains high estrogenic activity, and this reaction was how the drug was discovered, in the late 1930s. The drug is a highly active and potent estrogen by the oral or subcutaneous route. The reaction of equilenin or dihydroequilenin with potassium hydroxide was also found to produce bisdehydrodoisynolic acid, the levorotatory isomer of which is an estrogen with an "astonishingly" high degree of potency, while the dextrorotatory isomer is inactive. Doisynolic acid was named after Edward Adelbert Doisy, a pioneer in the field of estrogen research and one of the discoverers of estrone.
A steroidogenesis inhibitor, also known as a steroid biosynthesis inhibitor, is a type of drug which inhibits one or more of the enzymes that are involved in the process of steroidogenesis, the biosynthesis of endogenous steroids and steroid hormones. They may inhibit the production of cholesterol and other sterols, sex steroids such as androgens, estrogens, and progestogens, corticosteroids such as glucocorticoids and mineralocorticoids, and neurosteroids. They are used in the treatment of a variety of medical conditions that depend on endogenous steroids.
Flugestone acetate, sold under the brand name Cronolone among others, is a progestin medication which is used in veterinary medicine.
Clogestone, also known as chlormadinol or as 3β,17α-dihydroxy-6-chloropregna-4,6-diene-20-one, is a steroidal progestin that was synthesized in 1964 and was investigated as a progestin-only contraceptive but was never marketed. A diacetate ester, clogestone acetate, also exists and similarly was never marketed.
17α-Epiestriol, or simply 17-epiestriol, also known as 16α-hydroxy-17α-estradiol or estra-1,3,5(10)-triene-3,16α,17α-triol, is a minor and weak endogenous estrogen, and the 17α-epimer of estriol. It is formed from 16α-hydroxyestrone. In contrast to other endogenous estrogens like estradiol, 17α-epiestriol is a selective agonist of the ERβ. It is described as a relatively weak estrogen, which is in accordance with its relatively low affinity for the ERα. 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibiting tumor necrosis factor α (TNFα)-induced vascular cell adhesion molecule 1 (VCAM-1) expression in vitro.
Dianethole is a naturally occurring organic compound that is found in anise and fennel. It is a dimeric polymer of anethole. It has estrogenic activity, and along with anethole and photoanethole, may be responsible for the estrogenic effects of anise and fennel. These compounds bear resemblance to the estrogens stilbene and diethylstilbestrol, which may explain their estrogenic activity. In fact, it is said that diethylstilbestrol and related drugs were originally modeled after dianethole and photoanethole.
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.
16α-Hydroxydehydroepiandrosterone sulfate (16α-OH-DHEA-S), also known as 16α-hydroxy-17-oxoandrost-5-en-3β-yl sulfate, is an endogenous, naturally occurring steroid and a metabolic intermediate in the production of estriol from dehydroepiandrosterone (DHEA) during pregnancy. It is the C3β sulfate ester of 16α-hydroxy-DHEA.
Emmenin was an orally active formulation of estrogen that was developed by James Collip at Ayerst and introduced in Canada in 1930 and the United States in 1934. It was originally an extract obtained from human placentae. At some point, it seems to have been changed to an extract of the urine of women who were in late pregnancy, which was equivalent in composition but was less expensive to source, and was essentially the same product as Progynon, a related estrogen developed by Adolf Butenandt at Schering and introduced in Germany. These estrogen products were the first orally active estrogens to be marketed for medical use.
Perlapine, sold under the brand names Hypnodine and Pipnodine, is a hypnotic and sedative of the tricyclic group which is marketed in Japan. It acts primarily as a potent antihistamine, and also has anticholinergic, antiserotonergic, antiadrenergic, and some antidopaminergic activity. The drug has relatively weak affinity for the dopamine D2 receptor (IC50 = 1,803 nM) and, in accordance, is said to be ineffective as an antipsychotic. However, it retains higher affinity for the dopamine D1 receptor (IC50 = 198 nM). Its IC50 values are 19 nM for the α1-adrenergic receptor, 4,945 nM for the α2-adrenergic recpetor, and 70 nM for the serotonin 5-HT2A receptor. Perlapine is closely related to clotiapine, clozapine, fluperlapine, loxapine, and tilozepine.
