Steroids and Derivatives

Applications Dutasteride α-Dimer is a dimer impurity of Dutasteride (D735000); a dual inhibitor of 5α-reductase isoenzymes type 1 and 2. Dutasteride is structurally related to Finasteride (F342000) and is used in the treatment of benign prostatic hyperplasia.
References Bakshi, R.K., et al.: J. Med. Chem., 38, 3189 (1995); Gisleskog, P.O., et al.: Brit. J. Clin. Pharmacol., 47, 53 (1999); Djavan, B., et al.: Expert Opin. Pharmacother., 6, 311 (2005)

Applications Anti-inflammatory.
References Buchwald, P., et al.: Steroids, 73, 193 (2008), Holbeck, S., et al.: Mol. Endocrinol., 24, 1287 (2010),

Impurity Clobetasol Propionate EP Impurity C
Applications 21-Chloro-9-fluoro-11β,17-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 17-Propionate (Clobetasol Propionate EP Impurity C) is an impurity of Clobetasol 17-Propionate (C583500), an topical corticosteroid with anti-inflammatory properties.
References Sugai, S., et al.: Chem. Pharma. Bull., 31, 12 (1983);

Stability Hygroscopic
Applications 4-Hydroxy Estrone 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 glucocorticoid that inhibits prolyl hydroxylase activity and used as an antiasthmatic and antiallergic drug.
References Kos-Kudla, B. et al.; J. Clin. Pharm. Ther., 28, 103 (2003); Hochhaus, G. et al.; Pharmaceut. Res., 7, 558 (1990); Counts, D. et al.: Mol. Pharmacol., 15, 99 (1979); Cutroneo, K. et al.; Mol. Pharmacol., 11, 632 (1975); Cutroneo, K. et al.: Mol. Pharmacol., 11, 44 (1975)

Applications 5β-Finasteride is an azasteroid and 5β-isomeric impurity of Finasteride (F342000).
References Cendrowska, I. et al.: J. Liq. Chrom. Rel. Technol., 22, 2259 (1999);

Applications Labelled Medroxyprogesterone, an orally active progestogen used in hormone replacement therepy (HRT), in the past has been used as a component of oral contraceptives.
References Pan, Q., et al.: Mol. Hum. Reprod., 13, 797 (2007), Matsson, P., et al.: J. Pharmacol. Exp. Ther., 323, 19 (2007), Jukosky, J.A., et al.: Bull. Environ. Contam. Toxicol., 81, 230 (2008), Cherkasov, A., et al.: J. Med. Chem., 51, 2047 (2008),

Applications Labelled Cholesterol (C432501). Cholesterol is the principal sterol of the higher animals. Cholesterol was found in all body tissues, especial in the brain, spinal cord, and in animal fats or oils. Cholesterol is the main constituent of gallstones.
References Rosin, Z., et al.: Physiol. Chem., 124, 282 (1923), Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1934), Gemant, et al.: Life Sci., 1, 233 (1962), Johnson, K., et al.: 4, 457 (1964),

Stability Hygroscopic
Applications 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 Metab. Disposition, 37, 417 (2009),

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.
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),

Applications A metabolite of Exemestane; exerts biological effects as an androgen.
References Howell, A., et al.: Lancet, 365, 60 (2005), Goss, P., et al.: Clin. Cancer Res., 10, 5717 (2004), Buzdar, A., et al.: Lancet Oncol., 7, 633 (2006), Coates, A., et al.: J. Clin. Oncol., 25, 486 (2007), Jordan, V., et al.: Steroids, 72, 7 (2007),

Applications A metabolite of Prednicarbate (P703700).
References Kumar, R., et al.: Steroids, 64, 310 (1999), Kauppi, B., et al.: Biol. Chem., 278, 22748 (2003), Buchwald, P., et al.: J. Med. Chem., 49, 883 (2006),

Applications A steroid produced by females having pheromone activities.
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),

Stability Hygroscopic
Applications A degradation product of Betamethasone (B327000).
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),

Applications (7α,11α,12α,17α)-11,12-Epoxy-17-hydroxy-3-oxo-pregn-4-ene-7,21-dicarboxylic Acid Lactone, Methyl Ester is an impurity of eplerenone (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.
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),

Applications Quinestrol is an estrogen-like compound.

Applications A metabolite of Mifepristone (M343975).
References Ringler, I., et al.: Metabolism, 13, 37 (1964), Gagne, D., et al.: J. Steroid. Biochem., 25, 315 (1986), Jang, G., et al.: Biochem. Pharmacol., 52, 753 (1996), Hild, S., et al.: Hum. Reprod., 15, 822 (2000), Gainer, E., et al.: Steroids, 68, 1005 (2003),

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),

Stability Light Sensitive
Applications An impurity of the selective FP prostaglandin receptor agonist Travoprost (T715600) used as an ocularly applied intraocular pressure reducing agent.

Stability Hygroscopic
Applications Budesonide (B689490) epimer R. Budesonide 22R epimer is more active than 22S epimer. 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), Clissold, S.P., et al.: Drugs, 28, 485 (1984),

Applications A metabolite of Estradiol (E888000). An estrogenic metabolite considerably less potent than the hormone Estradiol (E888000).
References Marrian, et al.: Biochem. J., 23,1090 (1929), Huffman, et al.: J. Biol. Chem., 169, 167 (1947),

Applications Labelled Betamethasone Dipropionate. A glucocorticoid. Used as anti-inflammatory and antibacterial ointment for dermatosis.
References Dahlman-Ghozlan, K., et al.: Exp. Dermatol., 13, 65 (2004), Gounni Abdelilah, S., et al.: Clin. Immunol., 120, 220 (2006), Hertl, M., et al.: J. Clin. Invest., 116, 1159 (2006),

Impurity Budesonide EP Impurity I
Applications 16α-Butyloxyprednisolone (Budesonide EP Impurity I) is an impurity of Budesonide (B689460), a non-halogenated glucocorticoid intended for the local treatment of lung disease.
References Ryrfeldt, Å., et al.: Eur. J. Respir. Dis., 122, 86 (1981); Vestbo, J., et al.: Lancet, 353, 1819 (1999)

Stability Hygroscopic
Applications Glycosides isolated from various species of Digitalis. 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 Novotny, J., et al.: J. Biol. Chem., 258, 14433 (1983), Farr, C., et al.: J. Med. Chem., 45, 3257 (2002), Van Dongen, M., et al.: Drug Discov. Today, 7, 471 (2002),

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 Labelled 4-Methoxyestrone (M226135). An endogenous estrogen metabolite, risk-factor for development of breast cancer.
References Beral, V., et al.: Lancet, 362, 419 (2003), Nelson, R., et al.: Clin. Chem., 50, 373 (2004), Malekinejad, H., et al.: J. Agric. Food Chem., 54, 9785 (2006),

Applications A steroid hormone with weak androgenic activity. It is metabolized from Testosterone (T155000) in the liver and is used in doping analysis to detect testosterone misuse. Controlled Substance.This compound is a contaminant of emerging concern (CECs).
References Park, J., et al.: J. Anal. Toxicol., 14, 66 (1990), Palonek, E., et al.: J. Steroid Mol. Biol., 55, 121 (1995), Aguilera, R., et al.: Clin. Chem. 47, 292 (2001), Flenker, U., et al.: Steroids, 73, 408 (2008),

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 Sodium Pregnenolone-17alpha,21,21,21-d4 Sulfate (CAS# 1485492-21-4) is a useful isotopically labeled research compound.

Applications Progesterone (P755900) metabolite.
References Christy H., et al.: J. Steroid Biochem., Mol., Biol., 116, 171 (2009), Peristera, O., et al.: Toxicol., Lett., 189, 219 (2009), Mori, T., et al.: Toxicol., Lett., 186, 123 (2009),

Applications A labelled Estradiol (E888000) derivative.

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 6α,9α-Difluoroprednisolone has shown to increase metastases and increase glucocorticoid activity in C57/BL6 mice.
References Albert, D., Zeidman, I.: Cancer Res., 22, 1297 (1962)

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),

Impurity Budesonide EP Impurity D
Stability Hygroscopic
Applications 21-Dehydro Budesonide (Budesonide EP Impurity D) is a Budesonide (B689490) impurity.
References Backes, S., et al.: Drug Metab. Rev., 34, 157 (2002), Vermeer, H., et al.: Clin. Endocrinol., 59, 49 (2003), Assi, K., et al.: J. Pharm. Biomed. Anal., 41, 325 (2006),

Applications An anti-inflammatory drug used in veterinary medicine. It is a corticosteroid with both glucocorticoid and mineralocorticoid activity and has been shown to increase the frequency of severe hypokalemia in healthy cows.
References Coffer, N.Y. et al.: Am. J. Vet. Res., 67, 1244 (2006); Seifi, H.A. et al.: J. Diary Sci., 90, 4181 (2007);

Stability Hygroscopic
Applications Dexamethasone (D298800) process impurity.

Applications A metabolite of Desogestrel.
References Back, D., et al.: Br. J. Clin. Pharmacol., 26, 23 (1988), Wienkers, L., et al.: Drug Metab. Dispos., 1990, 24, 610 (1990), Bourrie, M., et al.: J. Pharmacol. Exp. Ther., 277, 321 (1996), Ono, S., et al.: Xenobiotica, 26, 681 (1996),

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 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),

Stability Light Sensitive, Temperature Sensitive
Applications 25-Hydroxyvitamin D3 3-Hemisuccinate is a conjugate of 5-Hydroxyvitamin D3 (C125700), the principal circulating form of vitamin D3, formed in the liver by hydroxylation at C-25. Calcium regulator. Also used in the preparation and synthesis of antisera to be used in the immunoassay of 25-Hydroxyvitamin D3.
References Morii, et al.: Arch. Biochem. Biophys., 120, 513 (1967), Blunt, et al.: Biochemistry, 7, 3317 (1968), Liu, et al.: Science, 311, 1770 (2006),

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 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 6β-Μethyl Prednisolone 21-Acetate is the 6-methyl isomer of 6α-Methyl Prednisolone 21-Acetate (M326030).
References Sugihara, N., et al: Am. J. Cardiol., 69, 1475 (1992), Bracken, M.B., et al.: J. Neurosurg., 89, 699 (1998), Dammers, J.W.H.H., et al.: Brit. Med. J., 319, 884 (1999).