Steroids and Derivatives

<p>Impurity Cyproterone Acetate EP Impurity F<br>Applications Cyproterone (Cyproterone Acetate EP Impurity F) is an antiandrogen, suppresses Testosterone and its metabolites. Derivatives of Cyproterone are administered to patients suffering from hypersexuality and to help facilitate the sexual transformation of male-to-female transsexuals.<br>References Gracia, T., et al.: Toxicol. App. Pharmacol., 225, 142 (2007), Ahlin, G., et al.: J. Med. Chem., 51, 5932 (2008), Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010), Bovee, T., et al.: J. Steroid Biochem. Mol. Biol., 118, 85 (2010),<br></p>

<p>Impurity Budesonide EP Impurity C, Budesonide Impurity C,<br>Applications 16α,17-[(1RS)-butylidenebis(oxy)]-11β-hydroxy-17-(hydroxymethyl)-D-homoandrosta-1,4-diene-3,17a-dione (Budesonide EP Impurity C) is an impurity of Budesonide (B689490), an antiinflammatory agent.<br>References Ferraboschi, P. et al.: J. Pharm. Biomed. Anal., 47, 636 (2008);<br></p>

<p>Stability Light Sensitive<br>Applications A synthetic, nonsteroidal estrogen.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Al-Badr, A.A., et al.: Anal. Profiles Drug Subs., 19, 145 (1990),<br></p>

<p>Applications A potent inhibitor of estrone sulfatase. Inhibits estrone sulfatase &gt;99% at 0.1uM in intact MCF-7 cells, IC50=65pM.<br>References Woo, L.W., et al.: J. Med. Chem., 41, 1068 (1998)<br></p>

<p>Applications A metabolite of Etonogestrel.<br></p>

<p>Applications It is a synthetic 17-lactone steroid which is a renal competitive aldosterone antagonist in a class of pharmaceuticals called potassium-sparing diuretics, used primarily to treat ascites in patients with liver disease, low-renin hypertension, hypokalemia, and Conn’s syndrome. A representative lot was 19% d3; 47% d6; 12% d7; 7% d8; 3% d9; 3% d10 and 8% d11.<br>References Sutter, J.L., et al.: Anal. Profiles Drug Subs., 4, 431 (1975),<br></p>

<p>Applications A metabolite of Mifepristone.<br>References Heikinheimo, O., et al.: J. Steroid Biochem., 26, 279 (1987), Brogden, R., et al.: Drugs, 45, 384 (1993), Shi, Y., et al.: Contraception, 48, 133 (1993), Jang, G., et al.: Biochem. Pharmacol., 52, 753 (1996), Gainer, E., et al.: Steroids, 68, 1005 (2003),<br></p>

<p>Applications A metabolite of Estradiol. It is an estrogenic steroid synthesized exclusively by the fetal liver during human pregnancy and reaching the maternal circulation through the placenta.<br>References Gurpide, E., et al.: J. Clin. Endocrinol., 26, 1355 (1966), Hagen, A., et al.: J. Clin. Endocrinol., 30, 763 (1970), Schollberg, K., et al.: Exp. Clin. Endocrinol., 85, 204 (1985), Coelingh Bennink, H., et al.: Contraception, 77, 186 (2008),<br></p>

<p>Applications The major metabolite of the progestational agent Norgestrel (N689500).<br>References DeJongh, D.C. et al.: Steroids, 11, 649 (1968); Uniyal, J.P. et al.: Acta Endocrinol., 84, 155 (1977); Sisenwine, S.F. et al.: Drug Metab. Disp., 7, 1 (1979);<br></p>

<p>Stability Hygroscopic, Unstable in Solution<br>Applications (αR,​1S,​3S,​4R)​-α,​4-​Dimethyl-​2-​oxo-​3-​(3-​oxobutyl)​-​cyclohexaneacetic Acid is an impurity of Artemisin (A777500), an active antimalarial constituent of the tradional Chinese medicinal herb Artemisia annua L., Compositae, which has been known for almost 2000 years as Qinghao. Antimalarial.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Klayman, D.L., et al.: Science, 228, 1049 (1985), Price, R.N., et al.: Expert Opin. Invest. Drugs, 9, 1815 (2000), Meshnick, S.R., et al.: Int. J., Parasitol., 32, 1655 (2002),<br></p>

<p>Stability Hygroscopic<br>Applications Limaprost is an analog of Prostaglandin E1 with structural modifications intended to give it a prolonged half-life and greater potency. Limaprost is used as an antianginal.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Tsuboi, T., et al.: Arch. Int. Pharmacodyn., 247, 89 (1980), Adaikan, P.G., et al.: Prostaglandins Med., 6, 449 (1981), Kottegoda, S.R., et al.: Prostaglandins Leukotrienes Med., 8, 343 (1982), Ishizaki, T., et al.: Chest, 85, 382 (1984),<br></p>

<p>Impurity Spironolactone EP Impurity E<br>Applications 7β-Spironolactone (Spironolactone EP Impurity E) is the 7β-isomer of Spironolactone (S683000). It binds effectively to human plasma proteins.<br>References Chien, Y.W. et al.: J. Pharmac. Sci., 65, 1337 (1976);<br></p>

<p>Applications Testosterone Octanoate is a metabolite of testosterone (T155000), which is used in biological studies to determine the hemolytic and lipophilic activity of this anabolic steroid.<br>References Biagi, G.L., et al.: J. Med. Chem., 13, 944 (1970); Biagi, G. L., et al.: J. Med. Chem., 18, 873 (1975)<br></p>

<p>Applications Isotope labelled Ethynyl Estradiol (E685100), an oral contraceptive (1), is a synthetic steroid with high oral estrogenic potency. Used in estrogen replacement therapy (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.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References 1. Koetsawang, S. et al.: Contraception. 1982 March:25(3) p231-2412. Cuttler, L. et al.: J. Endocrinol. Metab. 1985 Jun;60(6):1087-92.<br></p>

<p>Applications Isotope labelled 17β-Estradiol (E888000), which is the major estrogen (1) secreted by the premenopausal ovary (2).Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.<br>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.<br></p>

<p>Impurity Clobetasol Propionate EP Impurity D<br>Applications 21-Chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregn-4-ene-3,20-dione 17-Propionate (Clobetasol Propionate EP Impurity D) is an impurity of Clobetasol 17-Propionate (C583500), an topical corticosteroid with anti-inflammatory properties.<br>References Olsen, E.A., et al.: J. Am. Acad. Dermatol., 15, 246 (1986),<br></p>

<p>Applications Labelled Limaprost (L461500). Limaprost is an analog of Prostaglandin E1 with structural modifications intended to give it a prolonged half-life and greater potency. Limaprost is used as an antianginal.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Tsuboi, T., et al.: Arch. Int. Pharmacodyn., 247, 89 (1980), Adaikan, P.G., et al.: Prostaglandins Med., 6, 449 (1981), Kottegoda, S.R., et al.: Prostaglandins Leukotrienes Med., 8, 343 (1982), Ishizaki, T., et al.: Chest, 85, 382 (1984),<br></p>

<p>Applications A metabolite of Equilin (E592800).<br>References Enmark, E., et al.: J. Clin. Endocrinol. Metab., 82, 4258 (1997), Wang, Z., et al.: J. Med. Chem., 43, 2419 (2000), Jiang, X., et al.: Steroids, 71, 334 (2006),<br></p>

<p>Applications Norgestrel (N689500) impurity.<br></p>

<p>Impurity Betamethasone Dipropionate EP Impurity U<br>Applications Betamethasone 9,11-Epoxide 17-Propionate (Betamethasone Dipropionate EP Impurity U) is an impurity of Betamethasone (B327000), an antiinflammatory agent.<br></p>

<p>Applications Progestogen. In combination with estrogen as oral contraceptive.<br>References Hahn, D.W., et al.: Contraception, 16, 541 (1977), Weintraub, H.S., et al.: J. Pharm. Sci., 67, 1406 (1978),<br></p>

<p>Applications 9-Desfluoro-11-dehydroxy-9(11)-ene Triamcinolone Acetonide is an impurity of Triamcinolone Acetonide (T767165) which is an antiasthmatic (inhalant) and antiallergic (nasal).<br>References Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972), Bernstein, I.L., et al.: Chest, 81, 20 (1982),<br></p>

<p>Impurity Levonorgestrel EP Impurity L<br>Applications D-Ethyl Gonendione (Levonorgestrel EP Impurity L) is a Norgestrel intermediate.<br>References Hiraga, K., et al.: Chem. Pharm. Bull., 13, 1289 (1965), Bergink, F.W., et al.: J. Steroid Biochem., 14, 175 (1981), Phillips, A., et al.: Contraception, 36, 181 (1987), Corson, S.L., et al.: Am. J. Obstet. Gynecol., 168, 1017 (1993),<br></p>

<p>Applications Isotope labelled Estrone (E889050), which is a metabolite of 17β-Estradiol (E888000). During the metabolism, it is in rapid equilibrium with Estriol (E888960) and 17β-Estradiol (E888000) (1). Causes the feminization of male fish at human and animal waste sites (2).Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.<br>References 1. Both, D. et al.: Anal. Prof. Drug Subst. 1983 12 pp135-1892. Goodman-Gruen, D. et al.: J. Clin. Endocrinol. Metab. 1996 Aug;81(8):2999-3003.<br></p>

<p>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.<br>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),<br></p>

<p>Impurity Estradiol EP Impurity C<br>Applications 4-Methyl Estradiol (Estradiol EP Impurity C) is an impurity of Estradiol (E888000).<br>References Zhu, B., et al.: Steroids, 70, 225 (2005), Enmark, E., et al.: J. Clin. Endocrinol. Metab., 82, 4258 (1997),<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of Estradiol (E888000).<br>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),<br></p>

<p>Applications Pregnenolone Carbonitrile is a glucocorticoid receptor antagonist that induces the expression of the CYP3A family of steroid hydroxylases and modulates sterol and bile acid biosynthesis in vivo. Pregnenolone Carbonitrile is an an activator of rat pregnane X receptor (PXR).<br>References Kliewer, S.A., et. al.: Cell, 92, 73 (1998); Savas, U., et. al.: Drug Metab. Dispos., 28, 529 (2000)<br></p>

<p>Applications A metabolite of Testosterone (T155000). It is a promising androgen for male hormonal contraception.CONTROLLED SUBSTANCE<br>References Glass, A., et al.: J. Clin. Endocrinol. Metab., 45, 1211 (1977), Behre, H., et al.: Eur. J. Endocrinol., 140, 414 (1999), Nieschlag, E., et al.: Steroids, 68, 965 (2003), Wang, C., et al.: J. Clin. Endocrinol. Metab., 91, 460 (2006),<br></p>

<p>Applications A metabolite of Cholesterol. Its membrane organizing properties could have implications in Altzheimer’s disease.<br>References Wang, J., et al.: Biochemistry, 43, 1010 (2004), Lemaire-Ewing, S., et al.: Cell Biol. Toxicol., 21, 97 (2005), Fuda, H., et al.: J. Lipid Res., 48, 1343 ( 2007), Sasaki, H., et al.: Metabolism, 56, 357 (2007); S.L. Regen et al.: J. Amer. Chem. Soc., 131, 12354 (2009)<br></p>

<p>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.<br>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),<br></p>

<p>Applications 20α-Dihydrodydrogesterone is the major active metabolite of dydrogesterone (D826000).<br>References Olbrich, M., et al.: Xenobiotica, 46, 868-874 (2016)<br></p>

<p>Applications Cortisone (C696500) derivative.<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of Exemestane (E957000).<br>References Cavalcanti, G. et al.: Steroids 76, 1010 (2011)<br></p>

<p>Applications Estrogen; antineoplastic (hormonal).<br>References Aboul-Enein, H.Y., et al.: Anal. Profiles Drug Subs., 11, 347 (1982),<br></p>

<p>Impurity Ethinylestradiol EP Impurity A<br>Applications 17-epi-Ethynyl Estradiol (Ethinylestradiol EP Impurity A) is the epimer derivative of Ethynyl Estradiol (E685100). An impurity.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Pomper, M., et al: J. Med. Chem., 33, 3143 (1990), Vulliet, E., et al.: Anal. Bioanal. Chem., 387, 2143 (2007), Muller, M., et al.: Environ. Toxicol. Chem., 27, 1649 (2008),<br></p>

<p>Applications Dexamethasone-biotin is biotin labelled Dexamethasone. Dexamethasone is a glucocorticoid used as an anti-inflammatory agent. Dexamethasone regulates T cell survival, growth, and differentiation. Dexamethasone inhibits the induction of nitric oxide synthase.<br>References Wershil, B.K., et al.: Int. Arch. Allergy Immunol., 107, 323 (1995), Riccardi, C., et al.: Cell Death Diff., 6, 1182 (1999), Llanos, S.L. and Roldan, A.: Bio Cell, 23, 29 (1999)<br></p>

<p>Applications 5β-Pregnane-3α,20α-diol is a metabolite of Progesterone (P755900).<br>References Beall, et al.: Biochem. J., 31, 35 (1937), Okuda, A., et al.: J. Biol. Chem., 259, 7519 (1984), Russell, D., et al.: Biochemistry, 31, 4737 (1992), Kondo, K., et al.: Eur. J. Biochem., 219, 357 (1994), Westerbacka, J., et al.: J. Clin. Endocrinol. Metab., 88, 4924 (2003),<br></p>

<p>Impurity Fluocinolone Acetonide EP Impurity A<br>Applications Fluocinolone Acetonide-21-carboxylic Acid, is a derivative of Fluocinolone Acetonide (F455800), which is a Corticosteroid, used in dermatology to reduce skin inflammation and relieve itching<br>References Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964), Emerson, M.V., et al.: BioDrugs, 21, 245 (2007),<br></p>

<p>Stability Hygroscopic<br>Applications Glucocorticoid.<br>References Ferrante, M.G., et al.: Anal. Profiles Drug Subs., 6, 43 (1977), Li, A., et al.: Chem. Biol. Interact., 142, 7 (2002), Cruz-Monteagudo, M., et al.: Eur. J. Med. Chem., 40, 1030 (2005), Rothfuss, A., et al.: Chem. Res. Toxicol., 19, 1313 (2006),<br></p>

<p>Applications 5α-Androstanedione is a metabolite of Androstendione (A637550). 5α-Androstanedione is an important intermediate in the conversion of Androstenedione to Androstanolone (A637540).<br>References Milewich, L., et al.: J. Steroid Chem., 16, 81 (1982); Stanczyk, F. Z., et al.: J. Steroid Biochem. Mol. Biol., 37, 129 (990);<br></p>

<p>Impurity Budesonide EP Impurity B<br>Applications Di-Norbudesonide (Budesonide EP Impurity B) is an impurity of Budesonide (B689490), an antiinflammatory agent.<br></p>

<p>Applications Estradiol (E888000) derivative. An estrogen.<br>References Salole, E.G., et al.: Anal. Profiles Drug Subs., 15, 283 (1986), Lievertz, R.W., et al.: Am. J. Obstet. Gynecol., 156, 1289 (1987),<br></p>

<p>Applications 6β-Hydroxy-11-deoxycortisol is a corticosteroid which is a metabolite of Cortisol (H714615), 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.<br>References Vigore, L., et al.: Cancer Ther., 6, 699 (2008), Puurunen, J., et al.: J. Clin. Endocrinol. Metab., 94, 1973 (2009), Lemos, D., et al.: J. Endocrinol., 201, 275 (2009), Chen, S., et al.: Am. J. Physiol., 296 (2009),<br></p>

<p>Stability Hygroscopic<br>Applications 4-Hydroxyestradiol 4-O-β-D-Glucuronide Sodium Salt, is a glucuronide derivative of 4-Hydroxy-17β-estradiol (H941895); a metabolite of Estradiol (E888000) which is the major estrogen secreted by the premenopausal ovary.<br>References Bucala, R., et al.: J. Clin. Endocrinol. Metab., 60, 841 (1985); Telang, N., et al.: Anticancer Res., et al.: 11, 1021 (1991); Seeger, H., et al.: Med. Sci. Res., 26, 481 (1998); Bolton, J., et al.: Chem. Res. Toxicol., 13, 135 (2000); Salole, E.G., et al.: Anal. Profiles Drug Subs., 15, 283 (1986); Lievertz, R.W., et al.: Am. J. Obstet. Gynecol., 156, 1289 (1987)<br></p>