Steroids and Derivatives

Applications Atorvastatin Derivative

Applications (Z)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.
References Yang, D. et al.: J. Lipid Res., 53, 529 (2012); El-Mekkawy, S. et al.: Nat. Prod. Res., 27, 146 (2013);

Impurity Betamethasone EP Impurity C
Applications (16β)-17,21-Dihydroxy-16β-methyl-pregna-1,4,9(11)-triene-3,20-dione (Betamethasone EP Impurity C) is used in biological studies to perform preclinical characterization of VBP15, a novel anti-inflammatory delta 9,11 steroid. This compound is also used in analytical studies to determine the stability from reversed-phase high performance liquid chromatography (RP-HPLC) to separate low levels of dexamethasone and other related compounds from betametasone, which is an active pharmaceutical ingredient.
References Reeves, E.K.M., et al.: Bioorg., Med. Chem., 21, 2241 (2013), Xiong, Y., et al.: J. Pharm. Biomed. Anal., 49, 646 (2009)

Impurity Betamethasone Valerate EP Impurity E
Applications Betamethasone 21-Valerate (Betamethasone Valerate EP Impurity E) is an isomeric impurity of Betamethasone 17-Valerate (B327075), as an corticosteroid. Betamethasone 21-Valerate was generated in the stress study of the active drug Betamethasone 17-Valerate (B327075).
References Caron, J.C., et al.: J. Pharmaceut. Sci., 73, 1703 (1984); Stouch, T.R., et al.: J. Med. Chem., 29, 2125 (1986);

Applications Testosterone 17-Decanoate, is an ester of Testosterone (T155000). Testosterone 17-Decanoate, can be used as a potential long-acting male contraceptive, with the combination of subcutaneous etonogestrel implants .
References Brady, B. M., et al.: Human Reproduction, 21 (1), 285 (2006); Themmen, A., et al.: Endocr. Rev. 21, 551 (2000);

Applications 17-Hydroxy-3,11-dioxo-androsta-1,4-diene-17β-carboxylic Acid is an intermediate used to prepare (11β,​17α)​-17-​[(Ethoxycarbonyl)​oxy]​-​11-​hydroxy-​3-​oxo-​androsta-​1,​4-​diene-​17-​carboxylic acid (E890570) which is a derivative of Loteprednol Etabonate (L471400), an ophthalmic corticosteroid.
References Alberth, M., et al.: J. Biopharm.Sci., 2, 115 (1991), Bodor, N., et al.: Pharm. Res., 9, 1275 (1992), Bartlett, J.D., et al.: J. Ocul. Pharmacol., 9, 157 (1993)

Impurity Ethinylestradiol EP Impurity D
Applications 17b-Estradiol is the major estrogen (1) secreted by the premenopausal ovary (2).This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
References 1. Salole, E. et al.: Anal. Profiles Drug Subs. 1986 15, 23 283-3182. Lievertz, R. et al.: Am. J. Obstet. Gynecol. 1987 May;156(5):1289-93.

Applications Glucocorticoid; antipsoriatic.
References Pearlman, R., et al.: Int. J. Pharm., 18, 53 (1984), Neufeld, E., et al.: J. Chromatogr., 718, 273 (1998),

Applications Dutasteride β-Dimer is a dimer impurity of Dutasteride (D735000); a dual inhibitor of 5α-reductase isoenzymes type 1 and 2. Dutasteride is structurally related to Finasteride (F342000) and is used in the treatment of benign prostatic hyperplasia.
References Bakshi, R.K., et al.: J. Med. Chem., 38, 3189 (1995); Gisleskog, P.O., et al.: Brit. J. Clin. Pharmacol., 47, 53 (1999); Djavan, B., et al.: Expert Opin. Pharmacother., 6, 311 (2005)

Applications di(4-Hydroxy Atorvastatin-d5) Calcium Salt is a labeled metabolite of Atorvastatin Calcium Salt (A791750), a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.
References Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993); Heinonen, T.M., et al.: Clin. Ther., 18, 853 (1996); Whitfield, L.R., et al.: Eur. J. Drug Metab. Pharmacokinet., 25, 97 (2000)

Applications Cardiotonic. Obtained by the O-methylation of Digoxin.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Hunter, J., et al.: J. Biol. Chem., 268, 14991 (1993), Greiner, B., et al.: J. Clin. Invest., 104, 147 (1999), Jun, A., et al.: J. Pharm.Pharm. Sci., 4, 263 (2001), Sugiyama, D., et al.: Drug Metab. Dispos., 30, 220 (2002),

Applications Steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.This compound is a contaminant of emerging concern (CECs).
References Anderson, E., et al.: Breast Cancer Res., 4, 197 (2002), Lanari, C., et al.: Breast Cancer Res., 4, 240 (2002), Albrecht, E.D., et al.: Front. Biosci., 8, 416 (2003), Qiu, M., et al.: J. Steroid Biochem. Mol. Biol., 85, 147 (2003),

Applications BGP 15 is a calcipotriene-based vitamin D3 analog that inhibits poly(ADP-ribose) polymerasesis (PARP), a class of enzymes that regulate DNA repair and apoptosis (1). BGP 15 is also a cardioprotective agent (2). Also, BPG 15 improves mitochondrial function, protects neurons from dying in vitro and in vivo, and promotes cardiac innervation in vivo.
References (1) Berkovich, L., et al.: Anticancer Drugs. 21, 609 (2010) (2) Szabados, E., et al. Biochem Pharmacol. 59, 937 (2000)

Applications A metabolite of Testosterone (T155000).
References Janer, G., et al.: Aquat. Toxicol., 75, 32 ( 2005), Lavado, R., et al.: Steroids, 71, 489 (2006),

Stability Hygroscopic
Applications A labelled metabolite of Estradiol (E888000).
References Agasan, A., et al.: J. Immunol. Methods., 177, 251 (1994), Stone, R., et al.: Science, 265, 308 (1994), Tacey, R., et al.: J. Pharm. Biomed. Anal., 2, 1303 (1994),

Applications D-Digitoxose is a derivative of D-ribo-Hexonic acid that is metabolized in the liver. It inhibits glucose-stimulated insulin release.
References Domschke, W. et al.: Naun.-Schmied. Arch. Pharmacol., 265, 149 (1969); Brown, D.F. et al.: Experientia, 39, 979 (1983); Hussain, M. et al.: Biochem. Biophys. Res. Comm., 129, 358 (1985);

Stability Hygroscopic
Applications Digitoxigenin has been used in a study to assess its stereochemical effects in cancer cytotoxicity. It has also been used in a study to investigate the advantage of gold(I)-catalyzed glycosidation of glycosyl o-alkyl benzoates to assemble digitoxin.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Hinds, J., et al.: Chemmedchem, 8, 63 (2013); Ma, Y., et al.: J. Org. Chem., 76, 9748 (2011)

Applications Labelled Estradiol. Estradiol (known as α-Estradiol or 17 α-Estradiol) is a biologically active estrogen in human breast cancer cells in tissue culture. 17-Εstradiol and its selective receptor, ER-X, are not part of a classical hormone/receptor endocrine system but of a system with important autocrine/paracrine functions in the developing and adult brain. 17-Estradiol may have enormous implications for hormone replacement strategies at the menopause and in the treatment of such neurodegenerative disorders as Alzheimer’s disease and ischemic stroke.
References Salole, E.G., Anal. Profiles Drug Subs., 15, 283 (1986), Lievertz, R.W., et al.: Am. J. Obstret. Gynecol., 156, 1289 (1987), Kuhnz, W., et al.: Arzneim.-Forsch., 43, 966 (1993),

Applications A Cholesterol (C432501) metabolite. Lathosterol (indicating cholesterol synthesis) and Sitosterol (indicating cholesterol absorption) also decreased with deteriorating health. Low Lathosterol, Sitosterol (S497050), and Cholesterol (C432501) predicted mortality additively and independently of each other.
References Chyou, P., et al.: Age Ageing, 29, 69 (2000), Schatz, I., et al.: Lancet, 358, 351 (2001), Bjorkman, M., et al.: Eur. J. Endocrinol., 158, 749 (2008),

Applications Cardiotonic; diuretic.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Sreenivasan, Y., et al.: Biochem. Pharmacol., 66, 2223 (2003), Ni, D., et al.: J. Exp. Ther. Oncol., 2, 278 (2002), Langford, S.D., Toxicology, 109,1 (1996),

Applications A major steroidal sapogenin from Radix ophiopogon japonicus with robust anti-inflammatory and anti-thrombotic activities. Studies suggest that it inhibits adhesion of leukocytes to a human umbilical vein endothelial cell line (ECV304) injured by tumor necrosis factor-α (TNF-α) in a concentration-dependent manner.
References Huang, Y. et al.: Drug Dev. Res., 69, 196 (2008); Huang, Y. et al.: J. Pharmacol. Sci., 108, 198 (2008); Song, J. et al.: J. Pharmacol. Sci., 113, 409 (2010);

Applications Gestrinone is a Steroidal antiestrogen, antiprogestogen, analog of Norgestrienone. Antigonadotropin.Controlled substance.
References Azadian-Boulanger, G., et al.: Am. J. Obstet. Gynecol., 125, 1049 (1976), Thomas, E.J., et al.: Br. Med. J., 294, 272 (1987), Coutinho, E.M., et al.: Fertil. Steril., 49, 418 (1988),

Applications (7α,17α)- 9,17-Dihydroxy-3-oxo-pregn-4-ene-7,21-dicarboxylic Acid Di-γ-lactone is an eplerenone (E588775) impurity. Eplerenone is a selective aldosterone receptor antagonist (SARA), structurally similar to Spiranolactone. Eplerenone is used alone or in combination with other medications to treat high blood pressure. Eplerenone is in a class of medications called mineralocorticoid receptor antagonists. It works by blocking the action of aldosterone, a natural substance in the body that raises blood pressure.
References de Gasparo, M., et al.: J. Pharmacol. Exp. Ther., 240, 650 (1987), Delyani, J.A., et al.: Cardiovasc. Drug Rev., 19, 185 (2001), Burgess, E., et al.: Expert. Opin. Pharmacother., 5, 2573 (2004), Ravis, W.R., et al.: J. Clin. Pharmacol., 45, 810 (2005),

Applications Labelled Cortisol (H714615). Cortisol, or Hydrocortisone, is a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.
References Hechter, O., et al.: Arch. Biochem. Biophys., 25, 457 (1950), Colingsworth, D.R., et al.: J. Biol. Chem., 203, 807 (1953), Florey, K., et al.: Anal. Profiles Drug Subs., 12, 277 (1983),

Applications Clobetasol Propionate Impurity E is an impurity of Clobetasol (C583490), which is a topical corticosteroid. Glucocorticoid; anti-inflammatory.
References Olsen, E.A., et al.: J. Am. Acad. Dermatol., 15, 246 (1986),

Stability Light Sensitive
Applications Fluocinonide 22 Methyl Homologue is a steriod and a derivative compound of Fluocinolone Acetonide (F455800) with anti-inflammatory activity.
References Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964), Emerson, M.V., et al.: BioDrugs, 21, 245 (2007),

Applications 7-Ketoabiraterone Acetate is an impurity of Abiraterone (A108490), a steroidal cytochrome P 450 17α-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer.
References Denis, L., et al.: Cancer, 72, 3888 (1993); Potter, G.A., et al.: J. Med. Chem., 38, 2463 (1995); Denmeade, S., et al.: Nat. Rev., 2, 389(2002); Scher, H., et al.: J. Clin. Oncol., 23, 8253 (2005)

Stability Hygroscopic
Applications α-Epoxyabiraterone Acetate is an impurity of Abiraterone (A108490), a steroidal cytochrome P 450 17α-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer.
References Denis, L., et al.: Cancer, 72, 3888 (1993); Potter, G.A., et al.: J. Med. Chem., 38, 2463 (1995); Denmeade, S., et al.: Nat. Rev., 2, 389(2002); Scher, H., et al.: J. Clin. Oncol., 23, 8253 (2005)

Applications A metabolite of Atorvastatin, a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.
References Smith, S., et al.: Am. J. Cardiol., 80, 10H (1997), Jacobsen, W., et al.: Drug Metab. Dispos., 28, 1369 (2000), Istvan, E., et al.: Science, 292, 1160 (2001), Tabernero, L., et al.: J. Biol. Chem., 278, 19933 (2003), Bratton, L., et al.: Bioorg. Med. Chem., 15, 5576 (2007),

Applications 4-Hydroxy Ospemifene is an Ospemifene (O703000) impurity, used to treat dyspareunia. It is a selective estrogen receptor modulator (SERM) acting similarly to an estrogen.
References Rutanen, E., et al.: Menopause, 10, 433 (2003);

Applications 1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one is an antioxidant and also has anti cancer effects on human breast cancer MCF-7 cells and Hep3B human hepatocellular carcinoma cells.
References Choi, Eun Jeong, et al.: Mol. Med. Rep., 9(1), 328-332 (2014);Choi, Eun Jeong, et al.: Onco.Lett., 6(6), 1784-1788 (2013);Choi, Eun Jeong, et al.: Inter. J.of Mol. Med., 31(3), 726-730 (2013)

Applications Δ1-Adrenosterone is a derivative of Adrenosterone (A305600), and is suspected to have some inhibitory effects on estrogen biosynthesis in human placental microsomes. Δ1-Adrenosterone also has potential androgenic anabolic and antiuterotropic activity.
References Lodge, B., et al.: Can. J. Pharm. Sci., 10, 107 (1975); Lodge, B., et al.: Can. J. Pharm. Sci., 11, 95 (1976); Schwarzel, W., et al.: Endocrinology, 92, 866 (1973)

Applications O,O-Dimethyl Methylphosphonate is a commercially used preignition additive for gasoline, anti-foaming agent, plasticizer, stabilizer and antistatic agents.
References Jang, S.H., et al.: J. Korean. Phy. Soc., 55, 294 (2009); Schneider, B.B., et al.: Int. J. Mass. Spectro., 298, 45 (2010);