Steroids and Derivatives

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

<p>Applications Δ6-Gestodene, is an impurity of Gestodene (G368250), an orally active gestogen with progesterone-like profile of activity. Used in combination with estrogen as oral contraceptive.<br>References Duesterberg, B., et al.: Contraception, 24, 673 (1981); Duesterberg, B., et al.: Seroids, 43, 43 (1984); Losert, W., et al.: Arzneim.-Forsch., 35, 459 (1985);<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>Applications A metabolite of Finasteride (F342000) in human bile (M2 metabolite).<br>References Faller, B., et al.: Biochemistry, 32, 5705 (1993), Carlin, J.R., Drug Metab. Dispos., 25, 100 (1997), Bergman, E., et al.: Eur. J. Pharm. Sci., 29, 205 (2006),<br></p>

<p>Impurity Ethinylestradiol EP Impurity M<br>Applications 2-Methylethynylestradiol (Ethinylestradiol EP Impurity M) is a 17α-ethynyl steroid. 2-Methylethynylestradiol is an impurity of Ethynylestradiol (E685100).<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 Estradiol. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.<br>References Miilunpohja, M., et al.: J. Steroid Biochem. Mol. Biol., 100, 59 (2006), Ikonomou, M., et al.: Environ. Toxicol. Chem., 27, 243 (2008),<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 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 (16α)-21-[(Ethoxycarbonyl)oxy]-17-hydroxy-16-methylpregna-1,4,9(11)-triene-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>Stability Hygroscopic<br>Applications Tixocortol is an anti-inflammatory agent. Tixocortol is used in fluorescent chemoaffinity labeling.<br>References Torossian, D.R., et al.: Arzneim.-Forsch., 31, 453 (1981),<br></p>

<p>Applications An impurity of Finasteride (F342000).<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>Applications Epoxy Metradiene is an impurity from 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>Impurity Progesterone EP Impurity E<br>Applications 20-Dihydroprogesterone Acetate (Progesterone EP Impurity E) is an analogue of Progesterone (P755900), a steroid used in cardiovascular and menopausal studies.<br>References Grodstein, F. et al.: New. Eng. J. Med., 335, 453 (1996); Cushman, M. et al.: Circulation, 100, 717 (1999);<br></p>

<p>Applications A labelled 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 6α,9α-Difluoroprednisolone has 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 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 A Dexamethasone Dipropionate metabolite.<br>References Miyachi, Y., et al.: Steroids, 52, 137 (1988), Soh H., et al.: Brit. J. dermatol., 125, 73 (1991), Civiale, C., et al.: J. Ocul. Pharmacol., Thera., 20, 75 (2004),<br></p>

<p>Applications Testosterone-16,16,17-d3 17-Phenylpropionate, is the labeled analogue of Testosterone 17-Phenylpropionate (T155150), a Testosterone ester being misused by athletes in an attempt to improve sports performance. It can also be used as a therapy in glucocorticoid-treated patients to increase the circulating testosterone concentration.<br>References Shackleton, C. H. L., et al.: Steroids, 62 (7), 523 (1997); Reid, I. R., et al.: Archives Internal Med., 156 (11), 1173 (1996);<br></p>

<p>(1β,2β,6β-7α)-17-(Acetyloxy)-6-chloro-1,2-dihydro-7-hydroxy<br>-3'H-cyclopropa[1,2]pregna-1,4-diene-3,20-dione; 6β-Chloro<br>-1β,2β-dihydro-7α,17-dihydroxy-3'Hcyclopropa[1,2]pregna-1,4-diene-3,20-dione 17-Acetate;<br>Cyproterone Acetate EP Impurity G</p>

<p>Stability Temperature Sensitive<br>Applications An epoxy impurity of the selective FP prostaglandin receptor agonist Travoprost (T715600).<br></p>

<p>Applications Atorvastatin-d5 tert-Butyl Ester is the labeled analogue of Atorvastatin tert-Butyl Ester (A791740), an impurity arising in the synthesis of Atorvastatin (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.<br>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)<br></p>

<p>Applications A labelled glucocorticoid microemulsion nasal preparation allergy inhibitor rhinitis.<br>References ukuoka, E., et al.: Chem. Pharm. Bull., 35, 2943 (1987), Schmitt, E., et al.: J. Pharm. Sci., 88, 291 (1999), Hancock, B., et al.: Pharm. Res., 17, 397 (2000), Hogan, S., et al.: Pharm. Res., 18, 112 (2001).<br></p>

<p>Impurity Latanoprost USP Related Compound D<br>Applications Latanoprost derivative. Latanoprost related compound D. Latanoprost USP Related Compound D.<br></p>

<p>Applications 4-Methylestrone is an intermediate in the synthesis of 4-substituted estrone and estradiol derivatives with inhibitory activities towards steroid sulfatase as a target for therapeutic intervention of treating breast cancer.<br>References Numazawa, M., et al.: J. Steroid. Biochem. Molec. Biol., 96, 51 (2005);<br></p>

<p>Applications A steroid produced by females having pheromone activities.<br>References Kotiyan, P., et al.: J. Pharm. Biomed. Anal., 22, 667 (2000), Bensafi, M., et al.: Behaviour. Brain Res., 152, 11 (2004), Zhu, B., et al.: Endocrinol., 147, 4132 (2006), Bellavance, E., et al.: J. Med. Chem., 52, 7488 (2009),<br></p>

<p>Applications 17α-Hydroxyprogesterone Heptanoate can be used in therapeutic use and biological study of pharmaceutical compounds and methods of use thereof for treating gender-biased immune disorders.<br>References Stoloff, G., et al.: PCT Int. Appl. WO 2016005599 A1 20160114 (2016)<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 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 1,2-Dihydro Triamcinolone is a derivative of Triamcinolone (T767165), a glucocorticoid, antiasthmatic (inhalant); 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>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 Carbenoxolone<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>