Steroids and Derivatives

Stability Light Sensitive
Applications 3β-Hydroxydesogestrel is a metabolite of Desogestrel (D296875), a progestogen with low androgenic potency.
References Viinikka, L., et al.: Eur. J. Clin. Pharmacol., 15, 349 (1979), Bergink, E.W., et al.: J. Steroid Biochem., 14, 175 (1981)

Impurity Fulvestrant EP Impurity A
Applications Fulvestrant (F862500) impurity A. The S-isomer of Fulvestrant.
References Sharman, G.J., et al.: Mag. Resonance Chem., 39, 549 (2001),

Applications A metabolite of Mifepristone.
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),

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.
References Sutter, J.L., et al.: Anal. Profiles Drug Subs., 4, 431 (1975),

Applications Progesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen.
References Schroff, A. P., et al.: Anal. Profiles Drug Subs., 4, 268 (1975), Singh, H., et al.: Am. J. Obstet. Gynecol., 135, 409 (1979), Toews, M., et al.: Curr. Ther. Res, 41, 509 (1987),

Applications 4-Hydroxyatorvastatin is a hydroxylated 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 A labelled metabolite of Estradiol (E888000).
References Marrian, B., et al.: Biochem. J., 59, 136 (1955), Dietel, M., et al.: Cancer Res., 50, 6100 (1990), Schumacher, G., et al.: Clin. Cancer Res., 5, 493 (1999), Robert, J., et al.: J. Med. Chem., 46, 4805 (2003),

Applications Pregna-​4,​9(11)​-​diene-​3,​20-​dione is a Progesterone (P755900) impurity, a 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.
References Thomas, P. et al.: Endocrinol., 148, 705 (2007); 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 A labelled glucocorticoid microemulsion nasal preparation allergy inhibitor rhinitis.
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).

Impurity Cyproterone Acetate EP Impurity F
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.
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),

Applications Labelled Metabolite of Testosterone (T155000).
References Shibata, N., et al.: Biochem. J., 368, 783 (2002), Sonneveld, E., et al.: Toxicol. Sci., 83, 136 (2005), Schulze, J., et al.: J. Clin. Endocrinol. Metab., 93, 2500 (2008), Sten, T., et al.: Drug

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

Stability Hygroscopic
Applications A metabolite of Digoxin (Dx) (D446575).
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 Fujii, Y., et al.: Clin. Chem., 37, 476 (1991), Salphati, L., et al.: Xenobiotica, 29, 171 (1999), Song, S., et al.: Drug Metab. Dispos., 27, 689 (1999),

Stability Hygroscopic
Applications Tixocortol is an anti-inflammatory agent. Tixocortol is used in fluorescent chemoaffinity labeling.
References Torossian, D.R., et al.: Arzneim.-Forsch., 31, 453 (1981),

Applications A labelled metabolite of Norgestimate.
References Phillips, A., et al.: Steroids, 55, 373 (1990)

Impurity Budesonide EP Impurity C, Budesonide Impurity C,
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.
References Ferraboschi, P. et al.: J. Pharm. Biomed. Anal., 47, 636 (2008);

Stability Hygroscopic
Applications Desonide 21-Acetate is a reactant in the synthesis of 7α-halogenocorticosteroids with anti-inflammatory activity.
References De, K., et. al.: J. Indian Chem. Soc., 79, 513 (2002)

Applications di(2-Hydroxy Atorvastatin) Calcium Salt is a 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 A synthetic diethyl-ether of Estradiol with no distal hormonal effects, in patients undergoing surgical correction for stress urinary incontinence (SUI).
References Kelleher, C., et al.: Br. J. Obstet. Gynaecol., 104, 1374 (1997), Deffieux, X., et al.: J. Gynecol. Obstet. Biol. Reprod., 35, 678 (2006),

Applications A metabolite of 17β -Estradiol (E888000).
References Cekan, S., et al.: J. Steroid Biochem., 27, 95 (1989), Martin, R., et al.: Clin. Chem., 46, 100 (2000), Blackwell, L., et al.: Steroids, 68, 465 (2003)

Applications An 5,6-trans isomeric impurity of the selective FP prostaglandin receptor agonist Travoprost (T715600).

Applications Protodioscin is a steroidal saponin compound found in a number of plant species. It is known to be the active component of the herbal aphrodisiac plant Tribulus terrestris. It has also shown to produce significant increases in the levels of the hormonal levels in animal studies.
References Gauthaman, K., et al.: Inter. J. Phytother. Phytopharm., 15, 44 (2008); Ganzera, M., et al.: J. Pharmac. Sci., 90(11), 1752 (2001);

Applications 11β,21-dihydroxypregna-1,4,16-triene-3,20-dione is a derivative of Prednisolone (P703740) and an intermediate in the synthesis of isoxazolinopregnadienes which exhibit anti-inflammatory activity.
References Khalil, M.A., et al.: Med. Chem. Res., 6, 52 (1996); Kwon, T., et al.: J. Med. Chem., 38, 1048 (1995)

Stability Hygroscopic
Applications Dexamethasone 21-Phosphate Dimer is a derivative of Dexamethasone (D298800), a glucocorticoid used as an anti-inflammatory agent. Dexamethasone regulates T cell survival, growth, and differentiation. Dexamethasone inhibits the induction of nitric oxide synthase.
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)

Impurity Estriol EP Impurity E
Applications 17-Epiestriol (Estriol EP Impurity E) is a metabolite of Estradiol.
References Marrian, B., et al.: Biochem. J., 59, 136 (1955), Dietel, M., et al.: Cancer Res., 50, 6100 (1990), Schumacher, G., et al.: Clin. Cancer Res., 5, 493 (1999), Robert, J., et al.: J. Med. Chem., 46, 4805 (2003),

Applications It is a potent and tissue-selective androgen receptor modulator (SARM) used as antiosteoporotic agent.
References Samnegard, E., et al.: Bone, 28, 414 (2001), Hanada, K., et al.: Biol. Pharm. Bull., 26, 1563 (2003), Kearbey, J., et al.: Xenobiotica, 34, 273 (2004), Kearbey, J., et al.: Xenobiotica, 34, 273 (2004), Kearbey, J., et al.: Pharm. Res., 24, 328 (2007),

Impurity Dutateride EP Impurity C
Applications Ethyl 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylate (Dutateride EP Impurity C) is a compound synthesized in the production of azasteroids. Used in the inhibition of 5α-reductase and of androgen receptor binding, both major effecters in the male hormonal system.
References Ramusson, G. et al.: J. Med. Chem., 29, 2298 (1986);

Applications Cardiotonic.
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 Aronson, J.K., et al.: Clin. Pharmacokinet, 5,137 (1980), Foss, P.R.B., Anal. Profiles Drug Subs., 9, 207 (1980),

Applications An aromatase inhibitor.
References Aello, A., et al.: J. Nat. Prod., 54, 281 (1991), Salaja, B.A., et al.: Steroids, 59, 330 (1994), Hunter, A.C., et al.: J. Steroid Biochem. Mol. Biol., 87, 301 (2003),

Applications 15-Keto Latanoprost is a metabolite of Latanoprost (L177280).
References Sjoquist, B., et al.: Drug Metab. Dispos., 26, 745 (1998), Watson, P., et al.: Drugs Today, 35, 449 (1999),

Applications 17,21-Dihydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione 21-Acetate is an intermediate in the synthesis of Mometasone Furoate (M490000), a tropical corticosteroid used as an anti-inflammatory agent.
References Spangler, M., et al.: Chromatograph., 54, 329 (2001); Reeves, E.K., et al.: Bioorg. Med. Chem., 21, 2241 (2013);

Applications A Cortisone derivative, a glucocorticoid.
References Mickelson, K., et al.: Biochemistry, 20, 6211 (1981), Westphal, U., et al.: J. Steroid Biochem., 19, 1 (1983),

Impurity Norethindrone Acetate EP Impurity F
Applications 6β-Hydroxy Norethindrone Acetate (Norethindrone Acetate EP Impurity F) is an oxidative product of the drug Norethindrone (N676000). Norethindrone impurity.
References Reif, V., et al.: Pharmaceutical Res., 4, 54 (1987), Rao, P., et al.: Steroids, 59, 621 (1994),

Impurity Estradiol EP Impurity A/ Ethinylestradiol EP Impurity C
Applications Estrone 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).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. 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.

Applications Labelled Norgestrel. It is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.
References Sopirak, A.M., et al.: Anal. Profiles Drug Subs., 4, 294 (1975), Dunson, T.R., et al.: Contraception, 48, 109 (1993),

Impurity Estriol EP Impurity C
Applications Estriol Methyl Ether (Estriol EP Impurity C) is a metabolite (1,2) of Estriol (E888960), which is a produced naturally and also a metabolite of Estradiol (E888000). Estriol is a GPR3 antagonist in estrogen receptor-negative breast cancer cells displaying anti-proliferative effects (3).
References 1. Marrian, G. et al.: Biochem. J. 1929;23(5):1090-8.2. Rogerson, B. et al.: Arch. Biochem. Biophys. 1986 Oct;250(1):70-85.3. Lappano, R. et al.: Mol Cell Endocrinol. 2010 May 14;320(1-2):162-70.

Applications Calcipotriol Monohydrate is a synthetic derivative of calcitriol, which is a biologically active form of Vitamin D3 (1). Calcipotriol Monohydrate can be used to treat psoriasis (2).
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 (1) Kim, D. H., et al.: Ann Dermatol. 24, 341 (2012) (2) Queille-Roussel, C., et al.: Clin Drug Investig (2016)

Applications 4-Hydroxy Estradiol 1-N7-Guanine is an estrogen metabolite formed with DNA which can lead to the mutations that initiate breast, prostate, and other types of cancer. Estrogen-DNA depurinating adducts as biomarkers of cancer risk and their use in cancer detection and prevention.
References Chakravarti, D., et al.: Mutat. Res., 456, 17 (2000), Liehr, J., et al.: Endocr. Rev., 21, 4054 (2000), Chakravarti, D., et al.: Oncogene, 20, 7945 (2001), Cavalieri, E., et al.: Chem. Res. Toxicol., 14, 1041 (2002),

Applications A 16α-substituted Prednisolone as potent topical antiinflammatory agent.
References Lutsky, B.N., et al.: Arzneim.-Forsch., 29, 1662 (1979),

Applications Anti-inflammatory.
References Phillips, et al.: Toxicol. Appl. Pharmacol., 20, 522 (1971), Sanen, F.J., et al.: Int. J. Clin. Pharmacol. Biopharm., 12, 174 (1975), Tarayre, J.P., et al.: Pharmacol., 19, 323 (1979).

Stability Hygroscopic
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.
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)