Steroids and Derivatives

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);

Applications (Z)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.
References Yang, D. et al.: J. Lipid Res., 53, 529 (2012); El-Mekkawy, S. et al.: Nat. Prod. Res., 27, 146 (2013);

Impurity Betamethasone EP Impurity C
Applications (16β)-17,21-Dihydroxy-16β-methyl-pregna-1,4,9(11)-triene-3,20-dione (Betamethasone EP Impurity C) is used in biological studies to perform preclinical characterization of VBP15, a novel anti-inflammatory delta 9,11 steroid. This compound is also used in analytical studies to determine the stability from reversed-phase high performance liquid chromatography (RP-HPLC) to separate low levels of dexamethasone and other related compounds from betametasone, which is an active pharmaceutical ingredient.
References Reeves, E.K.M., et al.: Bioorg., Med. Chem., 21, 2241 (2013), Xiong, Y., et al.: J. Pharm. Biomed. Anal., 49, 646 (2009)

Applications Prostaglandin analog, used to treat glaucoma and other degenerative diseases of the eye.
References Rhee, D.J., et al.: Clinic. Ophthalmol., 2, 313 (2008), Hernandez, M., et al.: Exp. Eye Res., 86, 798 (2008), Nagata, T., et al.: J. Pharmacol. Sci., 106, 423 (2008), Ikeda, Y., et al.: J. Ocular Pharmacol. Ther., 24, 230 (2008),

Applications 16α-Methylprednisolone is the 16α-Methyl analogue of Prednisolone (P703740). 16α-Methylprednisolone is an anti-inflammatory corticosteroid.
References Biju, P. et al.: Bioorg. Med. Chem. Lett., 22, 1086 (2012); Dausse, J.P. et al.: Mol. Pharmacol., 13, 948 (1977):

Applications Dienestrol is a metabolite of Diethylstilbestrol, a non-steroidal synthetic estrogen derivative.
References Liehr, J.G., et al.: Steroids, 40, 713 (1982); Yearley, E. et al.: J. Mol. Struct., 890, 240 (2008);

Applications 17α-Progesterone is a testosterone precursror generated from cholesterol. Also used as a diagnostic agent in the identification and study of ovarian Leydig cell tumor disease.
References Vesely, D. et al.: Proc. Natl. Acad. Sci. USA., 76, 3491 (1979); Arhan, E. et al.: J. Pediatric Endocrinol. Metab., 21, 181 (2008);

Applications A metabolite of Etiocholanolone.
References Eriksson, H., et al.: Eur. J. Biochem., 15, 132 (1970), Cook, D., et al.: Endocrinology, 93, 1019 (1973),

Applications Estradiol (E888000) derivative. An estrogen.
References Salole, E.G., et al.: Anal. Profiles Drug Subs., 15, 283 (1986), Lievertz, R.W., et al.: Am. J. Obstet. Gynecol., 156, 1289 (1987),

Applications (3α)-Allopregnanolone acts as a GABAA receptor positive allosteric modulator. (3α)-Allopregnanolone is a metabolite of Progesterone (P755900). (3α)-Allopregnanolone is a neuroactive steroid present in the blood and also the brain. In 2019, the US Food and Drug Administration approved (3α)-Allopregnanolone as an intravenous infusion for treating postpartum depression.
References Puja, G. et al.: Neuron, 4, 759 (1990); Belelli, D. et ael. Neurosteroid, 6, 565 (2006); Viapiano, M. et al.: Neurochem. Res., 23, 155 (1998);

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);

Applications Δ7-Avenasterol is an analog of Stigmasterol (S686750); a plant sterol that is used as a precursor in the synthesis of progesterone.
References Han, P., et al.: Biotechnol. App. Biochem., 54, 105 (2009); Matsunaga, I., et al.: Anal. Biochem., 393, 222 (2009); Huang, C., et al.: Plant Physiol., 150, 1192 (2009)

Applications 24(R/S)-Hydroxycholesterol-d7 is used in the study of biochemical methods for quantitative detection of steroids containing quantitative charge tags and oxidizing agents and using mass spectroscopy for detection.
References Groffoths, Williams., US 20150233953, (2015)

Applications 6β-Hydroxy-11-deoxycortisol is a corticosteroid which is a metabolite of Cortisol (H714615), 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.
References Vigore, L., et al.: Cancer Ther., 6, 699 (2008), Puurunen, J., et al.: J. Clin. Endocrinol. Metab., 94, 1973 (2009), Lemos, D., et al.: J. Endocrinol., 201, 275 (2009), Chen, S., et al.: Am. J. Physiol., 296 (2009),

Applications 7α-Hydroxy-4-cholesten-3-one is a metabolite of Cholesterol (C432501).
References Connor, W., et al.: J, Clin. Invest., 48, 1363 (1969), Nestel, P., et al.: Metabolism, 24, 189 (1975), Ellegard, L., et al.: Eur. J. Clin. Nutr., 45, 451 (1991), Pedersen, A., et al.: J. Lipid Res., 41, 1901 (2000),

Impurity Betamethasone Valerate EP Impurity E
Applications Betamethasone 21-Valerate (Betamethasone Valerate EP Impurity E) is an isomeric impurity of Betamethasone 17-Valerate (B327075), as an corticosteroid. Betamethasone 21-Valerate was generated in the stress study of the active drug Betamethasone 17-Valerate (B327075).
References Caron, J.C., et al.: J. Pharmaceut. Sci., 73, 1703 (1984); Stouch, T.R., et al.: J. Med. Chem., 29, 2125 (1986);

Applications The trans metabolite of Latanoprost (L177280), Prostaglandin analog.
References Botchkareva, N., et al.: FASEB J., 115, 645 (2001),

Applications A metabolite of Cholesterol (C432501).
References Marx, J., et al.: Science, 294, 508 (2001), Plosch, T., et al.: J. Biol. Chem., 277, 33870 (2002), Lund, E., et al.: J .Biol. Chem., 278, 22980 (2003),

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 An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It 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 Testosterone 17-Decanoate, is an ester of Testosterone (T155000). Testosterone 17-Decanoate, can be used as a potential long-acting male contraceptive, with the combination of subcutaneous etonogestrel implants .
References Brady, B. M., et al.: Human Reproduction, 21 (1), 285 (2006); Themmen, A., et al.: Endocr. Rev. 21, 551 (2000);

Applications A metabolite of Spironolactone.
References Morris, R., et al.: Eur. J. Clin. Pharmacol., 34, 233 (1988), Dasgupta, A., et al.: Am. J. Clin. Pathol., 111, 406 (1999)

Applications 5α-Pregnane-3β,20(S)-diol, is a metabolite of Progesterone (P755900).
References Beall, et al.: Biochem. J., 31, 35 (1937), Okuda, A., et al.: J. Biol. Chem., 259, 7519 (1984), Russell, D., et al.: Biochemistry, 31, 4737 (1992), Kondo, K., et al.: Eur. J. Biochem., 219, 357 (1994), Westerbacka, J., et al.: J. Clin. Endocrinol. Metab., 88, 4924 (2003),

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)

Applications 17-Hydroxy Pregnenolone, is a 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 Progesterone (P755900) impurity.
References Liang, T., et al.: Biol. Chem., 256, 7998 (1981), Bratoeff, E., et al.: J. Steroid Biochem. Mol. Biol., 111, 275 (2008),

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 Glucocorticoid; an intermediate in the biosynthesis of aldosterone, isolated from the adrenal cortex.
References Schmidt, M., et al.: Endocrinol., 150, 2709 (2009), Bailey, M., et al.: J. Immunol., 182, 7888 (2009), Brunton, P., et al.: J. Neurosci., 29, 6449 (2009), Pruett, S., et al.: Toxicol. Sci., 109, 265 (2009),

Applications Testosterone (T155000) derivative. It is a potent androgen with anabolic properties. Since the begining of the year 2005, the use of steroid precursors (prohormones) is illegal in the United States. Controlled substance.
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 Liao, S., et al.: J. Biol. Chem., 248, 6154 (1973), Saartok, T., et al.: Endocrinology, 114, 2100 (1984), Sugawara, T., et al.: J. Biol. Chem., 278, 42487 (2003),

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 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),

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),

Impurity Progesterone EP Impurity C
Applications 20β-Dihydroprogesterone (Progesterone EP Impurity C) is an impurity of Progesterone (P755900), a steroid hormone secreted by the corpus luteum. Progesterone have various significant physiological roles, such as inducing the maturation and secretory activities of the uterine endothelium and the suppression of ovulation. Progesterone is also implicated in the etiology of breast cancer.
References 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 5-(4-Fluorophenyl)-2,3-dihydro-3-(1-methylethyl)-2-oxo-N,4-diphenyl-1-[2-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1H-pyrrole-3-carboxamide is a photodegradation product of Atorvastatin (A791750).
References Cermola, F., et al.: Tetrahedron., 62, 7390 (2006);

Applications A synthetic steroid with weak estrogenic, androgenic and progestogenic activity. A pharamceutical used in the treatment of menopausal syndrome.
References de Visser, J., et al.: Arzneim.-Forsch., 34, 1010 (1984), Geusens, P., et al.: Maturitas Suppl, 1, 1 (1987)

Impurity Ethinylestradiol EP Impurity D
Applications 17b-Estradiol is the major estrogen (1) secreted by the premenopausal ovary (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. Salole, E. et al.: Anal. Profiles Drug Subs. 1986 15, 23 283-3182. Lievertz, R. et al.: Am. J. Obstet. Gynecol. 1987 May;156(5):1289-93.

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),

Applications Pregnenolone Carbonitrile is a glucocorticoid receptor antagonist that induces the expression of the CYP3A family of steroid hydroxylases and modulates sterol and bile acid biosynthesis in vivo. Pregnenolone Carbonitrile is an an activator of rat pregnane X receptor (PXR).
References Kliewer, S.A., et. al.: Cell, 92, 73 (1998); Savas, U., et. al.: Drug Metab. Dispos., 28, 529 (2000)