Steroids and Derivatives

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 metabolite of Norethindrone (N676000).
References Layne, D.S., et al.: Biochem. Pharmacol., 12, 905 (1963),

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 A labelled 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 (3β)-Cholesta-4,6-dien-3-ol is a Cholesterol (C432501) and Cholestane (C431700) derivative which has the potential to act as an antiinflammatory and antifungal compound.
References Felicio, R. et al.: J. Pharm. Biomed. Anal., 52, 763 (2010); 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),

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

Applications The 17α-metabolite of Equilin (E592800).
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),

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);

Applications 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 Isotope labelled intermediate in the synthesis of Dexamethasone (D298800), a glucocorticoid anti-inflammatory agent.
References Liu, Y., et al.: Anal. Bioanal. Chem., 395, 591 (2009), Rodgers, A., et al.: Chem. Res. Toxicol., 23, 724 (2010), Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010),

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),

Applications O,O-Dimethyl Methylphosphonate is a commercially used preignition additive for gasoline, anti-foaming agent, plasticizer, stabilizer and antistatic agents.
References Jang, S.H., et al.: J. Korean. Phy. Soc., 55, 294 (2009); Schneider, B.B., et al.: Int. J. Mass. Spectro., 298, 45 (2010);

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 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
Applications An impurity of Fluvastatin.

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),

Impurity Medroxyprogesterone Acetate USP Related Compound B
Applications An orally active progestogen used in hormone replacement therepy (HRT), in the past has been used as a component of oral contraceptives.SMedroxyprogesterone Acetate USP Related Compound B.
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 A 17β-estradiol ester as prodrug of Estradiol (E888000).
References Kabasakalian, P., et al.: J. Pharm. Sci., 55, 642 (1966), Marsh, M., et al.: Br. Med. Bull., 48, 426 (1992),

Applications Used as a reactant in the preparation of pyrimidinone ribosides and analogs that show anti-tumor properties.
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 Driscoll, J.S. et al.: J. Med. Chem., 34, 3280 (1991); Pan, L. et al.: J. Pharm. Biomed. Anal., 52, 589 (2010);

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)

Stability Temperature Sensitive
Applications Zilpaterol is a β-Adrenergic agonist. Growth promotant.
References Shelver, W.L., et al.: J. Agric. Food Chem., 52, 2159 (2004)

Impurity Prednicarbate USP Related Compound A
Applications 1,2-Dihydro Prednicarbate is a related compound of Prednicarbate (P703700). Prednicarbate related compound A. Prednicarbate USP Related Compound A.
References Conolly, et al.: J. Chem. Soc., 828 (1937),

Impurity Testosterone Decanoate EP Impurity I
Applications A metabolite of Testosterone (T155000). Controlled substance.
References Peng, S., et al.: Steroids, 67, 39 (2002), Pozo, O., et al.: Drug Metab. Dispos., 37, 2153 (2009),

Impurity Fluocinolone Acetonide EP Impurity A
Applications Fluocinolone Acetonide-21-carboxylic Acid, is a derivative of Fluocinolone Acetonide (F455800), which is a Corticosteroid, used in dermatology to reduce skin inflammation and relieve itching
References Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964), Emerson, M.V., et al.: BioDrugs, 21, 245 (2007),

Stability Light Sensitive, Temperature Sensitive
Applications The epimer metabolite of Calcifediol or 25-hydroxyvitamin D3 (C125700).
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 Sakaki, T., et al.: Eur. J. Biochem., 267, 6158 (2000), Kamao, M., et al.: J. Biol. Chem., 278, 1463 (2003),

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).

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),

Impurity Dutateride EP Impurity G
Applications 5,6-Dehydro-dutasteride (Dutateride EP Impurity G) is an impurity in the synthesis of Dutasteride (D735000), a dual inhibitor of 5α-reductase isoenzymes type 1 and 2; structurally related to Finasteride (F342000). Dutasteride 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 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).

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),

Applications A metabolite of Cholesterol. Its membrane organizing properties could have implications in Altzheimer’s disease.
References Wang, J., et al.: Biochemistry, 43, 1010 (2004), Lemaire-Ewing, S., et al.: Cell Biol. Toxicol., 21, 97 (2005), Fuda, H., et al.: J. Lipid Res., 48, 1343 ( 2007), Sasaki, H., et al.: Metabolism, 56, 357 (2007); S.L. Regen et al.: J. Amer. Chem. Soc., 131, 12354 (2009)

Applications A labelled metabolite of Estradiol (E888000).
References Fishman, H.G, et al.: Biochemistry, 8, 4304 (1969), Ryan, Sugar, J., et al.: J. Clin. Endocrinol. Metab., 50, 137 (1980), Numazawa, M., et al.: Steroids, 38, 149 (1981), Travis, R., et al.: Breast Cancer Res., 5, 239 (2003),

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

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 (3β)-Allopregnanolone Sulfate is the sulfate conjugate of (3β)-Allopregnanolone, a metabolite of progesterone and a potent inhibitory modulator of GABAA receptors.
References Li, P. et al.: Mol. Pharmacol., 77, 539 (2010); El-Etr, M. et al.: Brain Res., 790, 334 (1998); Park-Chung, M. et al.: Brain Res., 830, 72 (1999);

Stability Hygroscopic
Applications A labelled glucocorticoid, antiasthmatic (inhalant); antiallergic (nasal).
References Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972), Bernstein, I.L., et al.: Chest, 81, 20 (1982),

Applications A metabolite of Testosterone (T155000). It is a promising androgen for male hormonal contraception.CONTROLLED SUBSTANCE
References Glass, A., et al.: J. Clin. Endocrinol. Metab., 45, 1211 (1977), Behre, H., et al.: Eur. J. Endocrinol., 140, 414 (1999), Nieschlag, E., et al.: Steroids, 68, 965 (2003), Wang, C., et al.: J. Clin. Endocrinol. Metab., 91, 460 (2006),

Applications Preclinical profile of Ciclesonide, a novel corticosteroid for the treatment of asthma.
References Austin, R., et al.: Eur. Respir. J., 20, 1386 (2002), Belvisi, M.G., et al.: J. Pharmacol. Exp. Ther., 314, 568 (2005), Richter, K., et al.: J. Clin. Pharmacol., 45, 146 ( 2005).

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

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 Cortisol 21-Sulfate is a phase II metabolite of Cortisol (H714615).
References Spielgelhalder, B., et al.: J. Steroid Biochem., 7, 749 (1976), Vanluchene, E., et al.: J. Chromatogr., 456, 175 (1988), Choi, M., et al.: Steroids, 65, 54 (2000),

Applications 6α-Methyl-9α-fluoro-11β,17α-dihydroxyprogesterone is an impurity of Fluorometholone (F593145), 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 Palovarotene, is a highly selective retinoic acid receptor gamma (RAR-γ) agonist that is under investigation as a potential treatment for emphysema.
References Hind, M., et al.: Curr. Opinion Invest. Drugs, 10(11), 1243 (2009); Stolk, J., et al.: Therap. advances Respi. dise., 4, 319 (2010);