Steroids and Derivatives

<p>Applications Triamcinolone Acetonide (T767165) impurity.<br></p>

<p>Applications (11β)-9-Fluoro-11,21-dihydroxy-16-methyl-pregna-1,4,16-triene-3,20-dione is a derivative of Dexamethasone (D298800), an anti-inflammatory glucocorticoid.<br>References Kodelja, V., et al.: J. Immunol., 160, 1411 (1998), Metselaar, J., et al.: Arthritis Rheum., 48, 2059 (2003), Buttgereit, F., et al.: Arthritis Rheum., 50, 3408 (2004), Martinez, F., et al.: Front Biosci., 13, 453 (2008),<br></p>

<p>Applications 17α,21-Dideoxy-6α,​9α-Difluoroprednisolone is an impurity of the drug Difluprednate (D445925). Difluprednate is a corticosteroid (derivative of prednisolone), approved for the treatment of post-operative ocular inflammation.<br>References Kapp, A., et al.: J. Allergy and Clin. Immunol., 110, 277 (2002); Yasueda, S., et al.: J. Pharm. Biomed. Anal., 30, 1735 (2003); Yamaguchi, M., et al.: Int. J. Pharm., 301, 121 (2005)<br></p>

<p>Stability Hygroscopic<br>Applications A degradation product of Betamethasone (B327000).<br>References Andersson, P., et al.: J. Pharm. Pharmacol., 36, 763 (1984), Wurthwein, G., et al.: Biopharm. Drug Dispos., 11, 381 (1990), Samtani, M., et al.: J. Pharm. Sci., 93, 726 (2004), Samtani, M., et al.: Drug Metab. Dispos., 33, 1124 (2005),<br></p>

<p>Applications Labelled Dutasteride (D735000). Dutasteride is a dual inhibitor of 5α-reductase isoenzymes type 1 and 2; structurally related to Finasteride (F342000). Dutasteride is used in the treatment of benign prostatic hyperplasia.<br>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),<br></p>

<p>Applications (2Z)-2,3-Dehydroxy Atorvastatin is an intermediate in synthesizing (2E)-2,3-Dehydroxy Atorvastatin (D230045), which is an impurity in the synthesis of Atorvastatin (A791750).<br>References Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993); Heinonen, T.M., et al.: Clin. Ther., 18, 853 (1996);<br></p>

<p>Applications 17α-Hydroxy-progesterone Valerate acts as a synthetic Progesterone (P755900) reducing the chance of pre-term birth in women. Progesterone is a steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation<br>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),<br></p>

<p>Applications Progesterone (P755900) impurity.<br>References Liang, T., et al.: Biol. Chem., 256, 7998 (1981), Bratoeff, E., et al.: J. Steroid Biochem. Mol. Biol., 111, 275 (2008),<br></p>

<p>Applications 20β-Dihydrocortisone 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. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.<br>References Reach, G., et. al.: Steroids, 30, 621 (1977); 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>Impurity Levonorgestrel EP Impurity H<br>Applications 6β-Hydroxylevonorgestrel (Levonorgestrel EP Impurity H) is an impurity from the synthesis of Levonorgestrel (N689510), an oral contraceptive.<br>References Hu. S.H., et al.: Steroids., 63, 88 (1998); Nash, H.A., et al.: J. Pharma. Sci., 93, 2420 (2004); Choudhary, M.I., et al.: Natural. Prod. Res., 20, 1074 (2006);<br></p>

<p>Stability Light Sensitive, Temperature Sensitive<br>Applications An Atorvastatin (A791750) derivative which have improved stability.<br></p>

<p>Stability Hygroscopic<br>Applications 6α-9-Difluoroprednisolone-17-Carboxylate is an impurity of 6α,9α-Difluoroprednisolone (D446290), shown to increase metastases and increase glucocorticoid activity in C57/BL6 mice.<br>References Albert, D., Zeidman, I.: Cancer Res., 22, 1297 (1962)<br></p>

<p>Applications Preclinical profile of Ciclesonide, a novel corticosteroid for the treatment of asthma.<br>References Austin, R., et al.: Eur. Respir. J., 20, 1386 (2002), Belvisi, M.G., et al.: J. Pharmacol. Exp. Ther., 314, 568 (2005), Richter, K., et al.: J. Clin. Pharmacol., 45, 146 ( 2005).<br></p>

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

<p>Applications Sodium salt of Dexamethasone β-D-Glucuronide is a potential prodrug for colonic delivery of the antiinflammatory corticosteroid Dexamethasone.<br>References Fotsis, T., et al.: J. Steroid Biochem., 14, 457 (1981), Choi, M., et al.: Steroids, 65, 54 (2000); Haeberlin, B. et al.: Pharm Res., 10, 1553 (1993);<br></p>

<p>Applications Mestranol (M258755) derivative. It is used as contraceptive.<br>References Cullen, L.F., et al.: J. Pharma. Sci., 57, 1857 (1968),<br></p>

<p>Applications Testosterone 17-Decanoate-d3, is the labeled analogue of Testosterone 17-Decanoate (T155120), 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.<br>References Brady, B. M., et al.: Human Reproduction, 21 (1), 285 (2006); Themmen, A., et al.: Endocr. Rev. 21, 551 (2000);<br></p>

<p>Applications 16α-Hydroxypregna-4,9(11)-diene-3,20-dione is an intermediate in the synthesis of 16-Hydroxycorticosterone 20-Hydroxy-21-Acid (H918430), an oxidized derivative of corticosterone (C695700).<br>References Allen, G.R., et al.: J. Am. Chem. Soc., 81, 4968 (1959);<br></p>

<p>Applications A corticosteroid prodrug for the treatment of eye disorders.<br>References Benameur, H., et al.: J. Pharm. Pharmacol., 47, 812 (1995), Tauchi, Y., et al.: Biol. Pharm. Bull., 24, 925 (2001), Chono, S., et al.: J. Drug Targeting, 13, 407 (2005),<br></p>

<p>Applications N-Des(1,1-dimethylethyl) N-Cyclohexyl Finasteride is an impurity of Finasteride (F342000); an inhibitor of 5α-reductase which is the enzyme that converts testosterone to the more potent androgen 5α-dihydrotestosterone.Also an antialopecia agent.<br>References Koronkowski, M.J., et al.: Pharmacotherapy, 13, 309 (1993); Tenover, J.L., et al.: Clin. Ther., 19, 243 (1997); McConnell, J.D., et al.: N. Engl. J. Med., 338, 557 (1998)<br></p>

<p>Applications Labelled Testosterone (T155000). Principal hormone of the testes, produced by the interstitial cells. Major circulating androgen; converted by 5α-reductase in androgen-dependent target tissues to 5α-dehydrotestosterone which is required for normal male sexual differentiation. Also converted by aromatization to Estradiol.Controlled substance (anabolic steroid). Androgen.<br>References McFarland, K., et al.: Science, 245, 494 (1989), Heckert, L., et al.: Mol. Endocrinol., 12, 1499 (1998), Themmen, A., et al.: Endocr. Rev. 21, 551 (2000), Kumar, R., et al.: Biol. Reprod., 65, 710 (2001),<br></p>

<p>Applications A metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.<br>References Breuer, O., et al.: J. Lipid Res., 36, 2275 (1995), Pikuleva, I., et al.: J. Biol. Chem., 273, 18153 (1998), Chawla, A., et al.: Science, 294, 1866 (2001), Bodin, K., et al.: J. Biol. Chem., 276, 38685 (2001),<br></p>

<p>Stability Hygroscopic<br>Applications Prednisolone 21-Sulfate is a metabolite of Prednisolone (P703740).<br>References Hutzler, J., ET AL.: Drug Metab. Dispos., 30, 355 (2002), Sugiyama, D., et al.: J. Biol. Chem., 278, 43489 (2003), Hagenbuch, B., et al.: Xenobiotica, 38, 778 (2008),<br></p>

<p>Applications (3α)-Allopregnanolone 3-β-D-Glucuronide is the glucuronide conjugate of (3α)-Allopregnanolone (A547100), metabolite of progesterone and potent positive modulator of GABAA receptors.<br>References Martin, F. et al.: LJ Steroid Biochem., 6, 1339 (1975); Lin, M.T. et al.: Steroids, 32, 547 (1978);<br></p>

<p>Applications Labelled 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>Stability Not stable in Acidic or basic condition<br>Applications 6β-Methyl Fluorometholone is an impurity in the synthesis of Fluorometholone (F593145), a glucocorticoid; anti-inflammatory.<br>References Kupferman, A., et al.: Arch. Ophthlmol., 640, 100 (1982), Tokunaga H., et al.: Chem. Pharm. Bull., 32, 4012 (1984),<br></p>

<p>Applications Estrone-2,4-d2 (CAS# 350820-16-5) is a useful isotopically labeled research compound.<br></p>

<p>Applications Obeticholic Acid Methyl Ester is a bile acid derivative useful in research.<br>References Pellicciari, R., et al.: Journal of Medicinal Chemistry, 50, 4265 (2007)<br></p>

<p>Applications (6α,9β,11β,16α)-21-(Acetyloxy)-9,11-epoxy-6-fluoro-17-hydroxy-16-methylpregna-1,4-diene-3,20-dione is an intermediate in the synthesis of Paramethasone Acetate (P191845), a derivative of Dexamethasone (D298800), a potent synthetic member of the glucocorticoid class of steroid drugs that has anti-inflammatory and immunosuppressant properties.<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 6-keto Dexamethasone, is an impurity of Dexamethasone, 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></p>

<p>Applications Mexrenone is an impurity of eplerenon (E588775). 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 Betamethasone 21-Acetate-d3, is the labeled analogue of Betamethasone 21-Acetate (B327025), which is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties which can be used in treatment of asthma and itching.<br>References Kerns, E., et al.: J. Pharm. Sci., 90, 1838 (2001), Seidler, J., et al.: J. Med. Chem., 46, 4477 (2003), Alsenz, J., et al.: J. Pharm. Sci., 96, 1748 (2007),<br></p>

<p>Applications E-Ospemifene is the E-isomer of Ospemifene (O703000) and is useful for lowering serum cholesterol. It acts as a antiatherosclerotic and is also estrogen-like.<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 Sodervall, M., et al.: PCT Int. Appl. WO 9942427 A1 19990826. Aug 26, 1999<br></p>

<p>Applications Protected Estriol.<br>References Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010),<br></p>

<p>Applications Isotope labelled Equilenin (E592400), which is a naturally occuring estrogenic steroidal hormone (1,2) isolated from urine of pregnant mares (3). Not found in human urine. Component of conjugated estrogenic hormones. Estrogen. 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>References 1. Corbellini, A. et L.: Farmaco Sci. 1964 Nov;19:913-22.2. Stein, R. et al.: Tetrahedron 1970 Apr;26(8):1917-33.<br></p>

<p>Applications Fulvestrant 17-Ketone, is an impurity of Fulvestrant (F862500), a novel steroidal estrogen antagonist reported to lack any partial agonist activity. Antineoplastic (hormonal).<br>References Wakeling, A.E., et al.: Cancer Res., 51, 3867 (1991), Howell, A., et al.: Br. J. Cancer, 74, 300 (1996), Robertson, J.F., et al.: Cancer Res., 61, 6739 (2001),<br></p>

<p>Applications 23-Hydroxybudesonide is an metabolite of budesonide (B689490), a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.<br>References Edsbaecker, S., et al.: Drug. Metabol. Dispostion., 15, 403 (1987); Moore, C.D., et al.: Drug. Metabolism. Disposition., 41, 379 (2013);<br></p>