Steroids and Derivatives

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),

Applications Pregnenolone (P712200) derivative, a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens
References Bjondahl, K., et al.: Med. Biol., 54, 454 (1976), Geick, A., et al.: J. Biol. Chem., 276, 14581 (2001), Johnson, D., et al.: Toxicol. Sci., 66, 16 (2002), Abe, C., et al.: Lipids, 42, 637 (2007),

Applications Labelled Ulipristal (U700800). Ulipristal is a selective progesterone receptor modulator. Ulipristal is used during pregnancy.
References Gronemeijer, H., et al.: J. Steroid Biochem., 40, 271 (1991), Spitz, I., et al.: Contraception, 48, 403 (1993), Conneely, O., et al.: Steroids, 68, 771 (2003), Chwalisz, K., et al.: Endocr. Rev., 26, 423 (2005),

Applications A progestogen with low androgenic potency.
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 Viinikka, L., et al.: Eur. J. Clin. Pharmacol., 15, 349 (1979), Bergink, E.W., et al.: J. Steroid Biochem., 14, 175 (1981)

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

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),

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),

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 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),

Applications 5β-Dihydro Progesterone-d8 is labelled which is labelled 5β-Dihydro Progesterone (D449280), a metabolite of the neuroactive steroid Progesterone (PROG) (P755900).
References Wiebe, J., et al.: Cancer Res., 60, 936 (2000), Lacasa, D., et al.: J. Biol. Chem., 276, 11512 (2001), Johansson, I., et al.: Brain Res., 934, 125 (2002), Leonhardt, S., et al.: Steroids, 68, 761 (2003),

Applications Mifepristone is a progesterone receptor antagonist with partial agonist activity. Abortifacient.
References Healy, D.L., et al.: J. Clin. Endocrinol. Metab., 57, 863 (1983), Rauch, M., et al.: Eur. J. Biochem., 148, 213 (1985), Baulieu, E.E., et al.: Science, 245, 1351 (1989), Brogden, R.N., et al.: Drugs, 45, 384 (1993)

Applications Pregnenolone-d4, is the labeled analogue of the Pregnenolone (P712200), which is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens.
References Bjondahl, K., et al.: Med. Biol., 54, 454 (1976), Geick, A., et al.: J. Biol. Chem., 276, 14581 (2001), Johnson, D., et al.: Toxicol. Sci., 66, 16 (2002), Abe, C., et al.: Lipids, 42, 637 (2007),

Impurity Megestrol Acetate EP Impurity H
Applications (2α)-Methyl Megestrol Acetate (Megestrol Acetate EP Impurity H) is a related impurity in Megestrol acetate (M208050).
References Schneider, F., et al.: Helv. Chim. Acta, 56, 2396 (1973), Aisner, J., et al.: Semin. Oncol., 15, 68 (1988), Krischenowski, D., et al.: Steroids, 58, 278 (1993), Bratoeff, E., et al.: Chem. Pharm. Bull., 51, 1132 (2003),

Impurity Levonorgestrel EP Impurity M
Applications 6(7)-Dehydro Norgestrel (Levonorgestrel EP Impurity M) is a Norgestrel (N689500) impurity.
References Gorog, S., et al.: J. Chromatogr., 400 177 (1987),

Applications (11α,16α)-9,11-Epoxy-17,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione, can be used for the synthesis of Calicoferol E, a vitamin D3 analogues.
References Vir Singh, T., et al.: ARKAT USA, INc., (2002);

Applications Glucocorticoid; antipsoriatic.
References Pearlman, R., et al.: Int. J. Pharm., 18, 53 (1984), Neufeld, E., et al.: J. Chromatogr., 718, 273 (1998),

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 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 Gestodene is an orally active gestogen with a progesterone-like profile of activity. Gestodene is used in combination with estrogen as an oral contraceptive.
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),

Applications Sodium Estrone-2,4,16,16-d4 Sulfate (Stabilized with TRIS, 50% w/w) (CAS# 285979-80-8) is a useful isotopically labeled research compound.

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)

Impurity Betamethasone Acetate EP Impurity D
Applications 9β,11β-Epoxy-17,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 21-Acetate is an intermediate in the production of Betamethasone (B327000), which is a glucocorticoid used as an anti-inflammatory agent.
References Ferrante, M.G., et al.: Anal. Profiles Drug Subs., 6, 43 (1977), Li, A., et al.: Chem. Biol. Interact., 142, 7 (2002), Cruz-Monteagudo, M., et al.: Eur. J. Med. Chem., 40, 1030 (2005), Rothfuss, A., et al.: Chem. Res. Toxicol., 19, 1313 (2006)

Applications A metabolite of Tibolone. A synthetic steroid with weak estrogenic, androgenic and progestogenic activity. A pharamceutical used in the treatment of menopausal syndrome.
References Belman, S., et al.: Cancer Res., 32, 450 (1972), Shirahashi, H., et al.: Chem. Pharm. Bull., 41, 1664 (1993), Hoyte, R., et al.: Steroids, 58, 13 (1993), Sandker, G., et al.: Xenobiotica, 24, 143 (1994), Colombo, D., et al.: Eur. J. Med. Chem., 40, 69 (2005),

Applications Labelled Cortisol (H714615). Cortisol, or Hydrocortisone, is 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.
References Hechter, O., et al.: Arch. Biochem. Biophys., 25, 457 (1950), Colingsworth, D.R., et al.: J. Biol. Chem., 203, 807 (1953), Florey, K., et al.: Anal. Profiles Drug Subs., 12, 277 (1983),

Stability Hygroscopic
Applications 17β-Estradiol 3-O-Sulfate is a neuroactive steroid used in the studies of human recombinant p1 γ-aminobutyric acid type C (GABAC) recptors.
References Li, W.J., et al.: J. Pharmacol. Exp. Therp., 323, 236 (2007); Schneider, C., et al.: Steroids., 69, 245 (2004);

Applications A systemic corticosteroid. 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 A derivatives of Dexamethasone (D298800), an analog of cortical hormones.
References Giesen, E.M., et al.: Molec. Cell. Endocrinol., 22, 153 (1981),

Applications Prednisolone (P703740) metabolite.
References Garg, V., et al.: Biopharm. Drug Disposition, 15, 163 (1994), Adham, N., et al.: Proc. Biochem., 38, 897 (2003),

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

Applications A metabolite of Androstenedione (A637550).
References Gazdar, A., et al.: Cancer Res., 50, 5488 (1990), Levesque, J., et al.: Steroids, 70, 305 (2005), Lootens, L., et al.: Drug Metab. Dispos., 37, 2367 (2009),

Impurity Finasteride EP Impurity B
Applications 3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester (Finasteride EP Impurity B) is an impurity of Finasteride (F342000) and Dutasteride (D735000). An intermediate in the synthesis of Finasteride and Dutasteride, 5α-reductase inhibitors used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders. Finasteride impurity.
References Bakshi., et al.: J. Med. Chem., 38, 3189 (1995),

Applications Isotope labelled Ethynyl Estradiol (E685100), an oral contraceptive (1), is a synthetic steroid with high oral estrogenic potency. Used in estrogen replacement therapy (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.
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. Koetsawang, S. et al.: Contraception. 1982 March:25(3) p231-2412. Cuttler, L. et al.: J. Endocrinol. Metab. 1985 Jun;60(6):1087-92.

Applications 5α-Androstanedione is a metabolite of Androstendione (A637550). 5α-Androstanedione is an important intermediate in the conversion of Androstenedione to Androstanolone (A637540).
References Milewich, L., et al.: J. Steroid Chem., 16, 81 (1982); Stanczyk, F. Z., et al.: J. Steroid Biochem. Mol. Biol., 37, 129 (990);