Steroids and Derivatives

Applications 25-Hydroxy Cholesterol-d6, is the labeled analogue of 25-Hydroxy Cholesterol (H918030), which is an oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It also induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative regulation of c-Myc.
References Aupeix, K. et al.: Immunobiology, 194, 415 (1995); Moog, C. et al.: Antivir. Chem, Chemother., 9, 491 (1998); Ayala-Torres, S. et al.: Exp. Cell Res., 246, 193 (1999);

Applications A metabolite of Estradiol (E888000).
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),

Applications An impurity of Methylhydrocortisone.
References Wang, C., et al.: Steroids, 66, 811 (2001),

Applications Testosterone ester. Testosterone 17-Valerate has been a useful compound in the development of immunochemical techniques for detection of anabolic androgenic steroids in food supplements.
References Ruelle, P., et al.: Int. J. Pharm., 157, 219 (1997), de la Torre, X., et al.: J. Pharm. Biomed. Anal., 24, 645 (2001), Adat, S., et al.: Lett. Drug Des. Discov., 1, 334 (2004), Holubova, B., et al.: Eur. Food Res. Technol., 245, 1011 (2019)

Applications A labelled metabolite of Budesonide (B689490), a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.
References Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979), Roth, G., et al.: J. Pharm. Sci., 69, 766 (1980), Edsbaecker, S., et al.: Drug Metab. Dispos., 15, 412 (1987),

Impurity Ethinylestradiol EP Impurity G
Applications An oxidative tranformation product of Norethindrone Acetate (N675990) and Ethynyl Estradiol (E685100).
References Ekhato, I.V. et al.: Steroids, 67, 165 (2002); Lane. P.A. et al.: J. Pharmac. Sci., 76, 44 (1987);

Stability Light Sensitive, Temperature Sensitive
Applications 25-Hydroxyvitamin D3 3-Sulfate is a metabolite of 24,25-Dihydroxyvitamin D3 and 25-Hydroxyvitamin D3 (C125700).
References Higashi, T. et al.: Steroids, 65, 281 (2000); Higashi, T. et al.: Ann. Clin. Biochem., 36, 43 (1999);

Applications 19-Hydroxyandrostendione is a novel substituted estrogen as aromatase inhibitor. It induces neuroendocrine trans-differentiation of prostate cancer cells via an ectopic olactory receptor.
References Polan, M., et al.: J. Clin. Endocrinol. Metab., 70, 480 (1990), Kawasaki, T., et al.: Clin. Exp. Rheumatol., 18, 743, (2000), Castagnetta, L., et al.: Clin. Cancer Res., 8, 3146 (2002); Frontiers in Oncology, May 2018, vol. 8, article 162; https://doi.org/10.3389/fonc.2018.00162; Gen. Eng. and Biotech. News (https://www.genengnews.com/gen-news-highlights/could-prostate-cancer-be-treated-with-aromatherapy-in-the-future/81255862)

Applications Androstane Spin Label (ASL) is a spin labelled Androstane used to mimic Androstane.
References Scheidt, H., et al.: J. Biol. Chem., 278, 45563 (2003);

Applications An inhibitor of steroid biosynthesis. Used as an adrenocortical suppressant. Used in the treatment of breast cancer.
References Komanicky, P., et al.: J. Clin. Endocrinol. Metab., 47, 1042 (1978), Mori, Y., et al., Chem. Pharm. Bull., 29, 2646 (1981), Williams, C.J., et al.: Cancer Treat. Rep., 71, 1197 (1987)

Impurity Norethindrone Acetate EP Impurity G
Applications 6-Oxo Norethindrone Acetate (Norethindrone Acetate EP Impurity G) is an oxidative product of Norethindrone acetate (N675990).
References Schroff, A.P., et al.: Anal. Profiles Drug Subs., 4, 268 (1975); Singh, H., et al.: Am. J. Obstet. Gynecol., 135, 409 (1979)

Applications 3β,5α-Tetrahydrodeoxycorticosterone is a novel derivative of the steroid Dehydroepiandrosterone (DHEA), a known uncompetitive inhibitor of Glucose 6-Phosphate Dehydrogenase (G6PD). Studies have shown that 3β,5α-Tetrahydrodeoxycorticosterone may have potential function in the modulation of calcium and GABAA-gated chloride channel currents found in rat and guinea-pig neurons.
References Hamilton, N.M., et al.: J. Medn. Chem., 55, 4431 (2012); Ffench, M., et al.: Steriods., 64, 76 (1999);

Applications A 17β-Estradiol (E888000) metabolite.
References Gerk, P., et al.: Drug Metab. Disposition, 32, 1139 (2004), Antignac, J., et al.: Steroids, 70, 205 (2005), Cole, T., et al.: J. Fish Biol., 68, 661 (2006), Hutchins, S., et al.: Env. Sci. Technol., 41, 7192 (2007),

Applications b-Adrenergic agonist. Zipaterol, is used to promote growth. Zilpaterol is used to increase the size of cattle.
References Shelver, W.L., et al.: J. Agric. Food Chem., 52, 2159 (2004),

Applications Derivative of 19-Nortestosterone. In combination with estrogen as oral contraceptive. Progestogen.
References Hubner, M., et al.: Arzneim.-Forsch., 30, 401 (1980), Spona, J., et al.: Contraception, 56, 185 (1997), Foster, R.H., et al.: Drugs, 56, 825 (1998),

Applications The R-enantiomer of nonsteroidal selective androgen receptor modulator (SARM) Ostarine (O703500).

Applications Fluorometholone is a glucocorticoid; anti-inflammatory.
References Kupferman, A., et al.: Arch. Ophthlmol., 640, 100 (1982), Tokunaga H., et al.: Chem. Pharm. Bull., 32, 4012 (1984),

Applications Deflazacort-d3, is the labeled analogue of Deflazacort (D228975), a systemic corticosteroid, and a derivative of prednisolone. Used for rheumatoid arthritis and lupus.
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),

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 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),

Impurity Latanoprost USP Related Compound A
Stability Temperature Sensitive
Applications Prostaglandin analog; prodrug of active acid metabolite. It is a synthetic derivative of the natural prostaglandin PGF2α, used as an anti-glaucoma agent that is effective in various types of glaucoma and ocular hypertension. Latanoprost USP Related Compound A.
References Resul, B., et al.: J. Med. Chem., 36, 2242 (1993), Toris, C., et al.: Ophthalmology, 100, 1297 (1993), Holmstrom, S., et al.: Curr. Med. Res. Op., 21, 1875 (2005),

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

Applications A labelled metabolite of Pregnenolone (P712200).
References Kramer, R., et al.: J. Steroid Biochemi., 18, 715 (1983), Hiwatashi, A., et al.: J. Biochem., 98, 619 (1985), Eiichi, T., et al.: J. Pharmacol. Sci., 95, 140 (2004),

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 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.

Impurity Fulvestrant EP Impurity B
Applications A metabolite of Fulvestrant (F862500).
References Rao, P., et al.: J. Steroid Biochem., 25, 417 (1986), Wakeling, A., et al.: J. Steroid Biochem. Mol. Biol., 43, 173 (1992), DeFriend, D., et al.: Cancer Res., 54, 408 (1994),

Impurity Norethindrone Acetate EP Impurity C
Applications Δ-5(6)-Norethindrone Acetate (Norethindrone Acetate EP Impurity C) is an impurity of Norethindrone Acetate (N675990).

Impurity Estriol EP Impurity F
Applications 16-Epiestriol (Estriol EP Impurity F) 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 Atorvastatin Derivative

Applications 17-Hydroxy-3,11-dioxo-androsta-1,4-diene-17β-carboxylic Acid is an intermediate used to prepare (11β,​17α)​-17-​[(Ethoxycarbonyl)​oxy]​-​11-​hydroxy-​3-​oxo-​androsta-​1,​4-​diene-​17-​carboxylic acid (E890570) which is a derivative of Loteprednol Etabonate (L471400), an ophthalmic corticosteroid.
References Alberth, M., et al.: J. Biopharm.Sci., 2, 115 (1991), Bodor, N., et al.: Pharm. Res., 9, 1275 (1992), Bartlett, J.D., et al.: J. Ocul. Pharmacol., 9, 157 (1993)

Impurity Cholecalciferol EP Impurity E
Stability Light Sensitive, Temperature Sensitive, Unstable in DMSO
Applications Tachysterol3 (Cholecalciferol EP Impurity E) is a bioactive, synthetic vitamin D3 analog.
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 Bouillon, R., et al.: Endocr. Rev., 16, 200 (1995), Ettinger, R., et al.: Adv. Drug Res., 28, 269 (1996), Doi, T., et al.: Tetrahedr. Lett., 45, 5727 (2004),

Applications Cardiotonic. Obtained by the O-methylation of Digoxin.
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 Hunter, J., et al.: J. Biol. Chem., 268, 14991 (1993), Greiner, B., et al.: J. Clin. Invest., 104, 147 (1999), Jun, A., et al.: J. Pharm.Pharm. Sci., 4, 263 (2001), Sugiyama, D., et al.: Drug Metab. Dispos., 30, 220 (2002),

Applications Dexamethasone Acid Ethyl Ester 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)

Applications BGP 15 is a calcipotriene-based vitamin D3 analog that inhibits poly(ADP-ribose) polymerasesis (PARP), a class of enzymes that regulate DNA repair and apoptosis (1). BGP 15 is also a cardioprotective agent (2). Also, BPG 15 improves mitochondrial function, protects neurons from dying in vitro and in vivo, and promotes cardiac innervation in vivo.
References (1) Berkovich, L., et al.: Anticancer Drugs. 21, 609 (2010) (2) Szabados, E., et al. Biochem Pharmacol. 59, 937 (2000)

Impurity Calcipotriol EP Impurity C
Stability Temperature Sensitive
Applications The trans-isomeric impurity of Calcipotriene (C144200) and a vitamin D3 analogue with antitumor effects.
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 Wietrzyk, J. et al.: Anti-Cancer Drugs, 18, 447 (2007); Wietrzyk, J. et al.: Anticancer Res., 27, 3387 (2007); Filip, B. et al.: J. Ster. Biochem. Mol. Biol., 121, 399 (2010);

Applications A metabolite of Estradiol.
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),

Applications Diethylstilbestrol dipropionate

Applications A Cholesterol (C432501) metabolite. Lathosterol (indicating cholesterol synthesis) and Sitosterol (indicating cholesterol absorption) also decreased with deteriorating health. Low Lathosterol, Sitosterol (S497050), and Cholesterol (C432501) predicted mortality additively and independently of each other.
References Chyou, P., et al.: Age Ageing, 29, 69 (2000), Schatz, I., et al.: Lancet, 358, 351 (2001), Bjorkman, M., et al.: Eur. J. Endocrinol., 158, 749 (2008),

Applications A metabolite of 17β-Estradiol.
References Cushman, M., et al.: J. Med. Chem., 38, 2041 (1995), D’Amato, R.J., et al.: Proc. Natl. Acad. Sci. USA, 91, 3964 (1994), Forsis, T., et al.: Nature, 368, 237 (1994)

Applications An oxidizing agent, especially in steroid synthesis.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package

Applications Tetrahydrodehydrocorticosterone inhibits aldosteronogenesis by intact cells at concentrations that inhibited angiotensin binding.
References Campanile, C.P., Goodfriend, T.L.: Steroids, 37, 681(1981)

Applications Gestrinone is a Steroidal antiestrogen, antiprogestogen, analog of Norgestrienone. Antigonadotropin.Controlled substance.
References Azadian-Boulanger, G., et al.: Am. J. Obstet. Gynecol., 125, 1049 (1976), Thomas, E.J., et al.: Br. Med. J., 294, 272 (1987), Coutinho, E.M., et al.: Fertil. Steril., 49, 418 (1988),