Steroids and Derivatives

<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>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 D-Homoanalog of Triamcinolone is a rearrangement product of the drug triamcinolone, an anti-inflammatory drug.<br>References Delaney, E. J.; et al.: Steroids, 59, 196 (1994)<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>

<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>Stability Light Sensitive, Temperature Sensitive<br>Applications An Atorvastatin (A791750) derivative which have improved stability.<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 Labelled Bexarotene (B336750). Used as an antineoplastic. A selective retinoid X receptor (RXR) agonist.<br>References Boehm, M.F., et al.: J. Med. Che., 37,2930 (1994), Gottardis, M.M., et al.: Cancer Res., 56, 5566 (1996), Mukherjee, R., et al.: Nature, 386, 407 (1997), Miller, V.A., et al.: J. Clin. Oncol., 15, 790 (1997)<br></p>

<p>Applications Betamethasone acetate (BA) 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 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>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 15-Keto Latanoprost is a metabolite of Latanoprost (L177280).<br>References Sjoquist, B., et al.: Drug Metab. Dispos., 26, 745 (1998), Watson, P., et al.: Drugs Today, 35, 449 (1999),<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>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 A potential metabolite of Exemestane (E957000).<br>References Buzzetti, F., et al.: Steroids, 58, 527 (1993),<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>Applications (5α)-17,17-Dimethyl-18-nor-2-oxaandrost-13-en-3-one is metabolite and impurity of the anabolic steroid Oxandrolone (O845050).<br>References Fragkaki, A.G. et al.: J. Steroid Biochem. Mol. Biol., 115, 44 (2009); Bi, H. et al.: J. Steroid Biochem. Mol. Biol., 42, 533 (1992);<br></p>

<p>Stability Hygroscopic<br>Applications (11β,16β)-11,21-bis(acetyloxy)-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione, is an impurity of Deflazacort, which is a systemic corticosteroid, used for rheumatoid arthritis and lupus.<br>References Nathansohn, G., et al.: J. Med. Chem., 10,799 (1967), Schiatti, P., et al.: Arzneim. Forsch., 30, 1543 (1980), Cavall-Perin, P., et al.: Eur. J. Clin. Pharmacol., 26, 357 (1984), Imbimbo, B., et al.: Adv. Exp. Med. Biol., 171, 241 (1984),<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 Protected Estriol.<br>References Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010),<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 The minor metabolite of Deflazacort.<br>References Bernareggi, A., et al.: J. Pharma. Biomed. Anal., 5, 177-81 (1987), Assandri, A., et al.: Xenobiotica, 13(3), 185 (1983), Martinelli, E., et al.: Drug Metab. Dispos., 7, 335 (1979),<br></p>

<p>Stability Moisture Sensitive<br>Applications (11β,16α)-9-Bromo-21-[(ethoxycarbonyl)oxy]-11-(formyloxy)-17-hydroxy-16-methylpregna-1,4-diene-3,20-dione is an impurity of Dexamethasone (D298800), a glucocorticoid used as an anti-inflammatory agent.<br>References Spangler, M., et al.: Chromatographia, 54(5/6), 329-334 (2001);Wershil, B.K., et al.: Int. Arch. Allergy Immunol., 107, 323 (1995)<br></p>

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

<p>Applications E-17-Deacetylnorgestimate is a metabolite of Norgestimate. A contraceptive for birth control used by women.Note- The oxime isomerizes when: 1) Heated in any solvent or heating the crystalline form 2) Dissolved in MeOH at room temperature very quickly 3) Dissolved in acetone or CHCl3 at room temperature in a couple of hours at room temperature4) In EtOAc or EtOAc/isooctane over a couple of days at RT. It is stable in the crystalline form.<br>References Phillips, A., et al.: Steroids, 55, 373 (1990); Rabiolo, A., et al.: Arch. Gynecol. Obstet., 294, 1317 (2016)<br></p>

<p>Applications 17-Hydroxypregn-5-ene-3,20-dione is used in the synthesis of physiologically active steroid esters and spirolactones that functions as potential aldosterone antagonists.<br>References Seletskii, B. M., et al.: Croat. Chem. Acta. , 58, 699 (1986)<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 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>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>Stability Hygroscopic<br>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.<br>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)<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>Stability Light Sensitive, Temperature Sensitive<br>Applications The epimer metabolite of Calcifediol or 25-hydroxyvitamin D3 (C125700).<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 Sakaki, T., et al.: Eur. J. Biochem., 267, 6158 (2000), Kamao, M., et al.: J. Biol. Chem., 278, 1463 (2003),<br></p>

<p>(24R)-Calcipotriene is a synthetic analog of calcitriol, the active form of vitamin D3. It is a proapoptotic agent that inhibits tumor growth by causing mitochondrial membrane potential collapse in cancer cells. (24R)-Calcipotriene has been shown to inhibit tumor growth in animals and human cells in vitro. This drug also potentiates the effects of other anticancer drugs such as doxorubicin and etoposide. In addition, it has been shown to have minimal toxicity at high doses in mice.</p>

<p>Dexamethasone EP Impurity K is an analytical standard for impurities in the drug product Dexamethasone EP. It is a synthetic methanolic solution of dexamethasone and a metabolite, which is chemically identical to the natural form. The purity of this impurity standard is 99.9%. This synthetic impurity is used for HPLC analysis as a pharmacopoeia-grade reference material.</p>

<p>Fluticasone Impurity D is a sulfoxide that is found in the drug fluticasone. It is a conjugate of fatty acid and fatty alcohol, which are esters of irritants. Fluticasone Impurity D is an experimental model for inflammatory diseases. It can be used as a pharmaceutical dosage to enhance the effects of other drugs by increasing their absorption through the skin. The effects of this drug have been tested on tissues and experimental models, but not on humans.</p>

<p>Rac5-Keto Fluvastatin is a synthetic, natural and custom synthesis drug product. It's CAS number is 1160169-39-0. Rac5-Keto Fluvastatin is a metabolite of fluvastatin. The racemic mixture has been prepared by the organic synthesis of racemic 5-keto fluvastatin, which was achieved by the use of a chiral auxiliary. Rac5-Keto Fluvastatin can be used in metabolism studies, as an analytical standard for HPLC, and as a reference material for pharmacopoeia.</p>

<p>5,6-Dehydro-17beta-dutasteride is a synthetic drug product that is used as an analytical standard for the determination of metabolites and impurities in pharmaceuticals. It also has been used as a natural metabolite, which can be found in human urine. 5,6-Dehydro-17beta-dutasteride is a metabolite of dutasteride, which is an antiandrogen medication for the treatment of benign prostatic hyperplasia (BPH). It is also known to inhibit the metabolism of other drugs such as ketoconazole and metoprolol.</p>

<p>Atorvastatin is a potent inhibitor of the enzyme HMG-CoA reductase, which is responsible for the conversion of HMG-CoA to mevalonate. This inhibition reduces the production of cholesterol and other lipids in the liver. Metabolism studies have shown that atorvastatin undergoes extensive presystemic metabolism by cytochrome P450 enzymes, primarily CYP3A4 and CYP2C9. The drug is converted to inactive metabolites that are eliminated primarily through renal excretion. Atorvastatin has not been found to inhibit any of the following: cytochrome P450 1A1/2, 2C8/9, 2D6, 2E1, 3A4/5 or glucuronidases.</p>

<p>Atorvastatin is a synthetic drug product. It is a prodrug that is converted to its active form, atorvastatin acid, in the body. Atorvastatin is used for lowering blood cholesterol levels in people with hypercholesterolemia and reducing the risk of coronary heart disease. This drug has been shown to reduce the number of deaths from coronary heart disease by 30% after five years of use. Atorvastatin also reduces the risk of stroke and fatal or non-fatal heart attack by 20%.</p>

<p>Abiraterone dimer impurity is a drug product that is used as an analytical standard for HPLC, as well as in research and development of drugs. It is also a metabolite of abiraterone and has been detected in the urine of patients receiving the drug. Abiraterone dimer impurity is found in trace amounts in abiraterone acetate but its pharmacological significance is not known. This impurity has been detected in the urine of patients receiving abiraterone acetate therapy.</p>

<p>(5E)-Calcipotriene is a synthetic, natural, and analytical chemical. It is a white to off-white powder with a melting point of about 122 °C. (5E)-Calcipotriene has been used as an analytical standard for HPLC and as an impurity in the synthesis of calcitriol. The International Union of Pure and Applied Chemistry (IUPAC) name for this compound is 5Z,7Z,11Z,15Z-eicosapentaenoic acid. It can also be found in the form of 5Z,8Z,11Z,14E-eicosapentaenoic acid.</p>