Steroids

Applications N-Desmethyl Ulipristal Acetate is the N-monodemethylated analogue and metabolite of the selective progesterone receptor modulator Ulipristal Acetate (U700810). N-Desmethyl Ulipristal Acetate contributes significantly to the antiprogestational activity of its parent compound.
References Attardi, B.J. et al.: J. Steroid Biochem. Mol. Biol., 88, 277 (2004);

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),

Stability Hygroscopic
Applications 3-Sulfoglycolithocholic Acid Disodium Salt is a derivative of Lithocholic acid (L469180). Lithocholic acid (LCA) is a putative tumor promoter,that is shown to be able to inhibit mammalian DNA polymerase β.
References Ogawa, A., et al.: Jap. J. Canc. Res., 89, 1154 (1998)

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),

Impurity Rocuronium EP Impurity C
Applications 17-Desacetyl Rocuronium Bromide (Rocuronium EP Impurity C) is a metabolite of Rocuronium (R639500), in human plasma.
References Kleef, U., et al.: J. Chromatogr., 621, 65 (1993), Proost, J., et al.: Br. J. Anaesth., 85, 717 (2000),

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

Stability Hygroscopic
Applications It is one of the mono-hydroxylated metabolite of Stanozolol (S684500), an internal standard in doping analysis.
References Chung, B., et al.: J. Anal. Toxicol., 14, 91 (1990), Schanzer, W., et al.: J. Steroid Biochem., 36, 153 (1990), Phillis, B., et al.: Eur. J. Pharmacol., 398, 263 (2000)

Applications Androst-4-ene-3,17-dione-2,2,4,6,6,16,16-d7 is an intermediate in the synthesis of Dehydroepiandrosterone-d5 which is the labeled analogue of Dehydro Epiandrosterone (D229585). Dehydro Epiandrosterone is a major secretory steroidal product of the adrenal gland; secretion progresively declines with aging. May have estrogen-or androgen-like effects depending on the hormonal milieu. Intracellularly converted to androstenedione. It is used in treatment of menopausal syndrome.
References Yahara, M., et al.: J. Toxicol. Sci., 2, 161 (1977), Morales, A.J., et al.: J. Clin. Endocrinol. Metab., 78, 1360 (1994), Ebeling, P., et al.: Lancet, 343, 1479 (1994),

Impurity Fluocinolone Acetonide EP Impurity I
Applications 14,15-Dehydro Fluocinolone Acetonide is an impurity of Fluocinolone Acetonide (F455800); a glucocorticoid and anti-inflammatory agent.
References Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964); Emerson, M.V., et al.: BioDrugs, 21, 245 (2007)

Applications Amcinonide (A576150) analog as glucocorticoid receptor agonists for the treatment of inflammation and allergic conditions.
References Woodford, R., et al.: Curr. Ther. Res., 26, 301 (1979),

Impurity Beclomethasone Dipropionate EP Impurity E
Applications 6α-Chlorobeclomethasone Dipropionate (Beclomethasone Dipropionate EP Impurity E) is an analogue of Beclomethasone Dipropionate (B131030), an antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical).
References Laube, B., et al.: J. Allergy Clin. Immunol., 101, 475 (1998); Harrison, L., et al.: Eur. J. Clin. Pharmacol., 58, 191 (2002); Maneechotesuwan, K., et al.: J. Allergy Clin. Immunol., 121, 43 (2008)

Applications S 23 is a selective androgen receptor modulator.
References Thevis, M., et al.: Drug Testing and Analysis, 2, 589 (2010); Jones, A., et al.; Endocr., 150, 385 (2009)

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 An oxidative product of the drug Norethindrone (N676000). Norethindrone impurity.
References Reif, V., et al.: Pharmaceutical Res., 4, 54 (1987), Rao, P., et al.: Steroids, 59, 621 (1994),

Impurity Beclomethasone Dipropionate EP Impurity F
Applications 6α-Bromo Beclomethasone Dipropionate (Beclomethasone Dipropionate EP Impurity F) is an impurity of Beclomethasone Dipropionate (B131030).

β-Sitosterol β-D-glucoside is a phytosterol glycoside, which is primarily derived from plant sources such as fruits, vegetables, nuts, and seeds. As a natural component of plant cell membranes, it exhibits bioactive properties. The compound functions by modulating cholesterol metabolism and has anti-inflammatory, immunomodulatory, and antioxidant effects. It achieves this by interfering with the absorption of cholesterol in the intestines and modulating the activity of enzymes involved in its metabolism.

Androsta-1,4,6-triene-3,17-dione is a steroidal aromatase inhibitor, which is a synthetic compound derived from modifications of naturally occurring steroid structures. Its mode of action involves the inhibition of the aromatase enzyme. Aromatase catalyzes the conversion of androgens into estrogens, a critical step in the biosynthesis of estrogens. By inhibiting this enzyme, Androsta-1,4,6-triene-3,17-dione effectively reduces estrogen levels, which can be of particular interest in research environments exploring the role of estrogens in various biological processes.

Formononetin is a naturally occurring isoflavone, which is a type of phytoestrogen found predominantly in legumes like red clover and other related plant species. It is a secondary metabolite that influences various biological processes by interacting with estrogen receptors. Formononetin acts primarily by mimicking or modulating the activity of natural estrogens within the body, binding to estrogen receptors and influencing gene expression and cellular responses.

Withaferin A is a bioactive compound, which is a steroidal lactone with antiproliferative properties. It is derived from the medicinal plant *Withania somnifera*, commonly known as Ashwagandha. Withaferin A exerts its effects by modulating various signaling pathways, including the inhibition of NF-kB and induction of oxidative stress, which lead to apoptotic cell death in cancer cells and reduced inflammation.

Zuclomiphene is a selective estrogen receptor modulator (SERM), which is derived from clomiphene citrate, a mixture containing two isomers, zuclomiphene and enclomiphene. Zuclomiphene acts by binding to estrogen receptors, exhibiting both estrogenic and anti-estrogenic effects depending on the target tissue. This dual action makes it a valuable tool in modulating estrogen receptor activity for scientific research.

Brassicasterol is a phytosterol, which is synthesized by various plant sources, particularly found in the seeds of plants such as rapeseed, mustard, and some algae. As a sterol, it is structurally similar to cholesterol but differs by having a methyl group at C24. This characteristic structure plays a vital role in its mode of action, modulating membrane fluidity and cell signaling pathways in organisms. In mammalian systems, brassicasterol may contribute to the reduction of cholesterol absorption by competing for incorporation into micelles, thus influencing metabolic pathways related to lipid processing and absorption.

9,10-Secocholesta-5,7,10(19)-trien-3beta-ol is a secosteroid compound, which is predominantly derived from the photochemical conversion of 7-dehydrocholesterol in the skin upon exposure to ultraviolet B radiation. This compound undergoes a series of hepatic and renal hydroxylations to form active vitamin D metabolites, such as calcitriol. These active forms modulate calcium and phosphate homeostasis through a nuclear receptor-mediated mechanism that governs gene expression relevant to mineral metabolism.

Phytoestrogen with anti-cancer properties

Phytosterol with anti-osteoarthritic activity; inhibits cholesterol biosynthesis

Dioscin is a steroidal saponin, which is a naturally occurring compound found in various plants, notably in species such as Dioscorea nipponica and Dioscorea zingiberensis. These plants belong to the yam family, which are well-regarded for their medicinal properties. The mode of action of dioscin involves modulation of various biochemical pathways, including the suppression of inflammatory cytokines and inhibition of cancer cell proliferation. Additionally, dioscin has been shown to promote apoptosis in cancer cells through the activation of caspases and disruption of mitochondrial function.

Prednisolone is a synthetic corticosteroid, which is a derivative of the natural hormone cortisol. It is derived from the modification of the corticosteroid structure to enhance its anti-inflammatory and immunosuppressive properties. The mode of action of prednisolone involves binding to glucocorticoid receptors, leading to the modulation of gene expression. This results in the suppression of pro-inflammatory cytokines and the inhibition of various immune responses.

Polyphyllin B (Formosanin C) is a natural saponin compound, which is derived from the rhizomes of plants in the genus Paris, particularly Paris polyphylla. Known for its biological activity, Polyphyllin B functions primarily by disrupting cellular membranes and inducing apoptosis in cancer cells through various signaling pathways, including the mitochondrial pathway. This mechanism is attributed to its ability to interfere with cancer cell proliferation and promote cell death, making it a compound of interest in oncological research.

Pregnenolone acetate is a synthetic compound classified as a steroidal hormone precursor. It is derived from pregnenolone, which is a naturally occurring steroid hormone in the body. Pregnenolone is primarily synthesized from cholesterol, a fundamental component upon which steroidogenesis is based. The acetate form is an ester derivative, which can enhance stability and bioavailability.