Flashcards: Steroids

Prednimustine is a drug used in chemotherapy.

Androstenol, also known as 5α-androst-16-en-3α-ol (shortened to 3α,5α-androstenol or 3β-androstenol), is a steroidal pheromone and neurosteroid in humans and other mammals, notably pigs.

Fusidic acid is a bacteriostatic antibiotic that is often used topically in creams and eyedrops but may also be given systemically as tablets or injections.

Tetrahydrodeoxycorticosterone (abbreviated as THDOC; 3α,21-dihydroxy-5α-pregnan-20-one), also referred to as allotetrahydrocorticosterone, is an endogenous neurosteroid.

Cholesterol, from the Ancient Greek chole- (bile) and stereos (solid) followed by the chemical suffix -ol for an alcohol, is an organic molecule.

Batrachotoxin (BTX) is an extremely potent cardiotoxic and neurotoxic steroidal alkaloid found in certain species of frogs (poison dart frog), melyrid beetles, and birds (the pitohui, blue-capped ifrit, and little shrikethrush).

The steroidogenic acute regulatory protein, commonly referred to as StAR (STARD1), is a transport protein that regulates cholesterol transfer within the mitochondria, which is the rate-limiting step in the production of steroid hormones.

Testosterone undecanoate (USAN, BAN) (brand names Aveed, Andriol, Androxon, Cernos Depot, Nebido, Panteston, Restandol, Nebido-R, Reandron 1000, Undestor), or testosterone undecylate, is an androgen and anabolic steroid and a testosterone ester.

Dehydroepiandrosterone sulfate or DHEA-S is a metabolite of dehydroepiandrosterone (DHEA).

Spironolactone, marketed under the brand name Aldactone among others, is a medication primarily used to treat fluid build-up due to heart failure, liver scarring, or kidney disease.

Estradiol (abbreviated as E2), or 17β-estradiol, also known as estra-1,3,5(10)-triene-3,17β-diol, is a steroid and estrogen sex hormone, and the primary female sex hormone.

Veratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by abolishing inactivation of sodium ion channels.

Mestranol (INN, USAN, BAN, JAN) (brand names Devocin, Ovastol, Tranel), also known as ethinyl estradiol 3-methyl ether (EEME), is a synthetic, steroidal estrogen that has been widely used medically.

Chlormadinone (INN, BAN) is a steroidal progestin which was never marketed.

Trilostane is an inhibitor of 3 β-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome.

17α-Dihydroequilin, or α-dihydroequilin, also known as 7-dehydro-17α-estradiol, as well as estra-1,3,5(10),7-tetraen-3,17α-diol, is a naturally occurring, steroidal estrogen found in horses that is closely related to equilin, equilenin, and 17α-estradiol.

Pentagestrone acetate (brand names Gestovis, Gestovister), also known as 17α-acetoxyprogesterone 3-cyclopentyl enol ether, is a steroidal progestin of the 17α-hydroxyprogesterone group that was described in the literature in 1960 and introduced by Vister in Italy in 1961.

Flugestone acetate (FGA) (INN, BAN) (brand names Chronogest, Chrono-Gest, Cronolone, Synchro-Mate, Gyncro-Mate; former developmental code names NSC-65411, SC-9880), or flurogestone acetate (USAN), also known as 17α-acetoxy-9α-fluoro-11β-hydroxyprogesterone, is a steroidal progestin of the 17α-hydroxyprogesterone group that is used in veterinary medicine as an intravaginal sponge preparation to synchronize estrus in ewes and goats.

Hydroxyestrone diacetate (brand names Colpoginon, Colpormon, Hormobion, Hormocervix) (former developmental code name RD-310), or 16α-hydroxyestrone diacetate, also known as 3,16α-dihydroxyestra-1,3,5(10)-trien-17-one 3,16α-diacetate, is a semisynthetic, steroidal estrogen that is marketed in France, Spain, Brazil, and Argentina.

Estradiol palmitate (brand name Esmopal), also known as 17-hexadecanoylestradiol or estradiol 17-hexadecanoate, is a semisynthetic, steroidal estrogen.

Estradiol hemisuccinate (brand name Eutocol), or simply estradiol succinate, also known as estradiol 17β-hemisuccinate, is a semisynthetic, steroidal estrogen and an estrogen ester – specifically, the hemisuccinate ester of estradiol.

Estriol acetate benzoate (JAN) (brand name Holin-Depot), or oestriol diacetate benzoate (BAN), is a semisynthetic, steroidal estrogen.

Hydroxyprogesterone caproate (OHPC) (INN, USAN, JAN) (brand names Delalutin, Proluton, Makena, Prodrox, Hylutin, many others), also known as hydroxyprogesterone hexanoate (BANM), is a steroidal progestin and derivative of 17α-hydroxyprogesterone (17α-OHP) that is related to other 17α-OHP derivatives such as chlormadinone acetate, cyproterone acetate, medroxyprogesterone acetate, and megestrol acetate.

Clometerone (INN) (developmental code name L-38000), or clometherone (USAN), also known as 6α-chloro-16α-methylprogesterone, is a synthetic steroid and derivative of progesterone described as an antiandrogen and antiestrogen that was never marketed.

Chloroethynyl norgestrel (developmental code name WY-4355) is a steroidal progestin of the 19-nortestosterone group related to norgestrel that was investigated as an oral contraceptive in the 1970s but was never marketed.

24-Ethyl coprostanol (24-ethyl 5β-cholestan-3β-ol) is a 29 carbon stanol formed from the biohydrogenation of β-sitosterol (24-ethyl cholest-5en-3β-ol, 24-ethyl cholesterol) in the gastrointestinal tract of most higher animals, especially herbivores.

Algestone acetophenide (USAN) (brand names Neolutin, Droxone, Deladroxone, Decadroxone, Dexadroxate, Bovitrol), also known as dihydroxyprogesterone acetophenide (DHPA), is a steroidal progestin of the 17α-hydroxyprogesterone group that is used as a contraceptive.

Hydrocortisone 21-butyrate is a form of hydrocortisone butyrate.

Hippuristanol is a small molecule found in the coral Isis hippuris which was discovered by Jerry Pelletier and others of McGill University in Montreal, Canada.

Diosgenin, a steroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro.

Oxendolone (INN, USAN, JAN) (brand name Prostetin; former developmental code name TSAA-291), also known as 16β-ethyl-19-nortestosterone or 16β-ethyl-17β-hydroxy-4-estren-3-one, is a steroidal antiandrogen and progestin of the 19-nortestosterone group that has been marketed in Japan by Takeda for the treatment of benign prostatic hyperplasia (BPH) since 1981.

Estetrol (E4), or 15α-hydroxyestriol, is an estrogen steroid hormone, found in detectable levels in maternal serum at around week 20 of pregnancy.

Estradiol acetate (INN, USAN, BAN) (brand names Femtrace, Femring, Menoring), or estradiol 3-acetate, is a semisynthetic, steroidal estrogen and an estrogen ester – specifically, the 3-acetate ester of estradiol.

Estradiol cypionate (EC, E2C) (INN, USAN) (brand name Depo-Estradiol, many others), or estradiol cipionate, also known as estradiol 17β-cyclopentylpropionate or estradiol 17β-cyclopentanepropionate, is a semisynthetic, steroidal estrogen and an estrogen ester – specifically, the 17β-cyclopentylpropionate (or cypionic acid) ester of estradiol – which is marketed in the United States, Canada, Europe, and throughout much of the rest of the world.

Etynodiol (INN), or ethynodiol (BAN), also known as 3β-hydroxynorethisterone, is a steroidal progestin related to norethisterone which was never marketed.

Norethisterone acetate (NETA) (INN, BAN), also known as norethindrone acetate (USAN), sold under brand names including Primolut-Nor (major), Aygestin (US), Gestakadin, Milligynon, Monogest, Norlutate (US, CA), Primolut N, SH-420 (UK), Sovel, Styptin, and others, is a steroidal progestin of the 19-nortestosterone group with additional weak androgenic and estrogenic activity that is used orally as a hormonal contraceptive, in the treatment of gynecological disorders such as abnormal uterine bleeding, and as a component of hormone replacement therapy for menopause.

Norgestrienone (INN) (brand name Ogyline, Planor, Miniplanor), also known as Δ9,11-norethisterone or 17α-ethynyltrienolone (17α-ethynyltrenbolone), as well as 17α-ethynylestra-4,9,11-trien-17β-ol-3-one, is a steroidal progestin related to norethisterone that is used as a hormonal contraceptive, sometimes in combination with ethinyl estradiol.

Dienogest (INN, USAN, BAN, JAN) is a steroidal progestin of the 19-nortestosterone group.

Testosterone isocaproate (BAN) (brand names Sustanon 100 (discontinued), Sustanon 250, Omnadren 250), or testosterone 4-methylvalerate, is an androgen and anabolic steroid and a testosterone ester.

Norgesterone (INN), also known as norvinodrel, vinylestrenolone, or vinylnoretynodrel, as well as 17α-vinylestr-5(10)-en-17β-ol-3-one and 17α-vinyl-δ5(10)-19-nortestosterone, is a steroidal progestin of the 19-nortestosterone group that was first described in 1965.

Retroprogesterone, also known as 9β,10α-progesterone or as 9β,10α-pregn-4-ene-3,20-dione, is a synthetic steroid and stereoisomer of the natural progestogen, progesterone.

Estradiol phenylpropionate (EPP), also known as estradiol 17β-phenylpropionate, is a semisynthetic, steroidal estrogen.

7-Dehydrodesmosterol (or cholesta-5,7,24-trien-3-beta-ol) is a cholesterol intermediate.

1,4,6-Androstatriene-3,17-dione (ATD) is a potent irreversible aromatase inhibitor that inhibits estrogen biosynthesis by permanently binding and inactivating aromatase in adipose and peripheral tissue.

1-Androstenedione, or 5α-androst-1-ene-3,17-dione, also known as 4,5α-dihydro-δ1-androstenedione, is a synthetic androgen and anabolic steroid.

Bolandione, also known as 19-norandrostenedione (19-norandrost-4-en-3,17-dione), is a precursor of the anabolic steroid nandrolone.

Estradiol benzoate (INN) (brand names Agofollin, Diffolisterol, Progynon-B, many others), or oestradiol benzoate (BAN), is a synthetic ester, specifically the 3-benzoyl ester, of the natural estrogen, estradiol.

Gestodene (INN, USAN, BAN), also known as 15(16)-dehydrolevonorgestrel, as well as 17α-ethynyl-18-methylestra-4,15-dien-17β-ol-3-one, is a steroidal progestin of the 19-nortestosterone group related to levonorgestrel that is used in combination with ethinyl estradiol as a hormonal contraceptive.

Digitonin is a steroidal saponin (saraponin) obtained from the foxglove plant Digitalis purpurea.

Tibolone (INN, USAN, BAN) (brand name Livial, Tibofem), also known as 7α-methylnoretynodrel, is a synthetic steroid drug with estrogenic, progestogenic, and weak androgenic actions which was introduced in 1988 and is used widely in Europe, Asia, Australasia, and, with the exception of the United States (where it is not available), the rest of the world.

Promegestone (INN) (brand name Surgestone), also known as 17α,21-dimethyl-Δ9-19-norprogesterone or 17α,21-dimethyl-19-norpregna-4,9-diene-3,20-dione, is a steroidal progestin of the 19-norprogesterone group which was introduced in 1983 and is marketed in France, Portugal, and Argentina.

Quingestanol acetate (INN, USAN) (brand names Demovis, Pilomin, Riglovis, Unovis), also known as norethisterone acetate 3-cyclopentyl ether, is a steroidal progestin of the 19-nortestosterone group with additional weak androgenic and estrogenic activity which is used as an oral, once-a-month, or postcoital hormonal contraceptive.

Squalamine /ˈskweɪləmiːn/ is an aminosterol compound with potent broad spectrum antimicrobial activity discovered in the tissues of the dogfish shark (Squalus acanthias) by a team led by Michael Zasloff.

Cloxestradiol acetate (brand name Genovul), also known as 17-(2,2,2-trichloroethoxy)estradiol O,O-diacetate, is a synthetic, steroidal estrogen derived from estradiol.

Nilestriol (INN) (brand name Wei Ni An; developmental code name LY-49825), also known as nylestriol (USAN, BAN), is a synthetic, steroidal estrogen that was patented in 1971 and is marketed in China.

Estriol succinate (INN) (brand names Sinapause, Styptanon, Synapasa, Synapausa, Synapause, Hemostyptanon, Orgastyptin, Ovestin, Evalon), or oestriol succinate (BAN), also known as estriol disuccinate or estriol hemisuccinate, as well as estriol 16α,17β-di(hydrogen succinate), is a semisynthetic, steroidal estrogen that is marketed in Europe, Hong Kong, and Mexico and was introduced in 1966.

PH10 is a vomeropherine that is under development by Pherin Pharmaceuticals as a nasal spray for the treatment of major depressive disorder.

Quinestradol (INN, BAN) (brand names Colpovis, Colpovister, Pentovis), or quinestradiol, also known as estriol 3-cyclopentyl ether (E3CPE), is a synthetic estrogen which is no longer used clinically.

Megestrol acetate (MGA) (INN, USAN, BAN, JAN) (brand names Megace, Megace ES), also known as 17α-acetoxy-6-dehydro-6-methylprogesterone, is a steroidal progestin of the 17α-hydroxyprogesterone group that is used in the treatment of breast and endometrial cancer and as an appetite stimulant.

Mepitiostane (INN, JAN) (brand name Thioderon), also known as epitiostanol 17-methyloxycyclopentyl ether, is a steroidal antiestrogen, androgen, and anabolic steroid that is used in Japan as an antineoplastic agent in the treatment of breast cancer and is also used in the treatment of anemia of renal failure.

Minamestane (INN (former developmental code name FCE-24,928) is a steroidal aromatase inhibitor which was under development by Farmitalia-Carlo Erba as an antineoplastic agent in the mid-1990s but was never marketed.

Nomegestrol acetate (NOMAC) (INN, USAN, USAN) (brand names Lutenyl (alone) and Naemis, Zoely (with estradiol)), or 19-normegestrol acetate, also known as 17α-acetoxy-6-dehydro-6-methyl-19-norprogesterone or 17α-acetoxy-6-methyl-19-norpregna-4,6-diene-3,20-dione, is an steroidal progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups which was first introduced in the 1980s and is used orally in the treatment of gynecological disorders and menopausal symptoms and as a hormonal contraceptive.

Estrane is a steroid derivative, with a Gonane core.

Oleoyl-estrone (OE) is a fatty acid ester of estrone.

Dimethisterone (INN, USAN, BAN) (brand names Lutagan, Secrosteron), also known as 6α,21-dimethylethisterone, is a steroidal progestin related to ethisterone (17α-ethinyltestosterone).

7-Ketodehydroepiandrosterone (7-keto-DHEA), also known as 7-oxoprasterone,is a steroid produced by metabolism of the prohormone dehydroepiandrosterone (DHEA).

(Not to be confused with 17β-estradiol.) Alfatradiol (INN) (brand names Ell-Cranell Alpha, Pantostin in Germany), also known as 17α-estradiol, is a 5α-reductase inhibitor used topically for the treatment of androgenic alopecia (hair loss) in men and women.

Cholesteryl chloride, also called 3-chlorocholest-5-ene or 3β-chlorocholest-5-ene, is an organic chemical, an organochloride derivate cholesterol.