Steroids

Stability Hygroscopic Applications Halobetasol is a corticosteroid, an anti-inflammatory drug that is used to treat various dermatological conditions which mainly consist of various forms of psoriasis. References Marrero-Ponce, Y. et al.: Eur. J. Med. Chem., 46, 5736 (2011); Spuls, P. I. et al.: J. Dermatolog. Treat., 14, 21 (2003); Wong, J. et al.: J. Drugs, Dermatol., 11, 957 (2012);

Applications A derivative of Danazol (D145000). References Dowsett, M. et al.: Clin. Endocrinol., 24, 555 (1986);

Liriope muscari baily saponins C has an anti-thrombotic activity due to down-regulation of the increased mRNA expression levels of TF and IL-6.

Applications 2α-Cyano Mestanolone is a derivative of Mestanolone (M225790), an anabolic steroid. References Arriza, J., et al.: Science, 237, 268 (1987); Lill, M., et al.: J. Med. Chem., 47, 6174 (2004); Bledsoe, R., et al.: J. Biol. Chem., 280, 31283 (2005)

Stability Hygroscopic Applications Prednisolone 21-Sulfate is a metabolite of Prednisolone (P703740). References Hutzler, J., ET AL.: Drug Metab. Dispos., 30, 355 (2002), Sugiyama, D., et al.: J. Biol. Chem., 278, 43489 (2003), Hagenbuch, B., et al.: Xenobiotica, 38, 778 (2008),

Estetrol (E4) is a naturally occurring estrogen, which is synthesized by the human fetal liver. It acts as a selective estrogen receptor modulator with a unique mode of action differentially impacting various tissues. Estetrol selectively binds to estrogen receptors, thereby facilitating a range of estrogenic activities. Interestingly, it exhibits modest estrogenic effects on both the endometrium and breast tissue, reducing potential risks typically associated with hormone therapies. In its applications, Estetrol is primarily focused on the field of hormonal contraception and menopausal hormone therapy. Its selective receptor binding contributes to favorable efficacy and safety profiles. Estetrol is explored for use in contraceptive formulations, where its function as a mild estrogen aims to minimize adverse effects commonly associated with synthetic estrogens. Additionally, its role in menopausal treatment seeks to alleviate symptoms while mitigating risks such as thromboembolic events. The dual functionality in contraception and menopause, combined with a novel mechanism that offers tissue selectivity, makes Estetrol a promising agent in hormonal therapies.

Applications Labelled analogue of Testosterone Cypionate, an anabolic steroid with androgenic properties. Testosterone Cypionate is used for testosterone therapy in males with hypogonadism. Controlled Substance. References Rabkin, J.G., et al.: J. Clin. Psychopharmacol., 19, 19 (1999); Hajjar, R., et al.: J. Clin. Endocrinol. Metab., 82, 3793 (1997); Rhoden, E., et al.: J. Sex Med., 7, 277 (2010);

Gracillin can induce cell cycle arrest, oxidative stress, and apoptosis in HL60 cells, and has the potential to be developed as an antitumor agent.

Natural glycoside

Applications 17α-Methyl-5α-androstane-2β,3α,17β)-triol is a derivative of Madol (M108000, which is an anabolic steroid recently identified to be misused as a doping agent. The potency of Madol (DMT) to transactivate androgen receptor (AR) dependent reporter gene expression was two times lower as compared to dihydrotestosterone (DHT). References Zierau, O., et al.: Planta Med., 69, 856 (2003), Takahashi, M., et al.: Endocr. J., 51, 425 (2004), Labrie, F., et al.: J. Endocrinol., 184, 427 (2005),Friedel, A., et al.: Toxicol. Lett., 164, 16(2006),

Lactone

Betamethasone enol aldehyde Z isomer is a synthetic corticosteroid, which is derived from modifications of the naturally occurring glucocorticoid, cortisol. Its structure has been altered to enhance anti-inflammatory and immunosuppressive potency. As a Z isomer, it exhibits specific stereochemistry, potentially affecting its pharmacokinetics and interactions at the molecular level. The mode of action of this compound involves binding to glucocorticoid receptors, leading to the modulation of gene expression. This process results in the inhibition of pro-inflammatory cytokines and other mediators involved in immune responses. The distinct configuration of the Z isomer may enhance or modify certain binding affinities crucial for its efficacy. Betamethasone enol aldehyde Z isomer is primarily used in research settings focusing on understanding inflammatory pathways and designing therapeutic interventions for conditions like autoimmune disorders and chronic inflammation. Its applications also extend to studying receptor-ligand interactions and assessing the impact of stereochemistry in drug design.

Resibufogenin is a cytotoxic steroid isolated from the Chinese drug ChanSu, which exhibits the anti-proliferative effect against cancer cells through the degradation of cyclin D1 caused by the activation of GSK-3β. Resibufogenin can inhibit rectifier potassium current ( I K ) and transient potassium current ( I A ), it has pathological effects on central nervous system. Resibufogenin corrects hypertension in a rat model of human preeclampsia, it not only prevents the advent of hypertension and proteinuria, but also the development of intrauterine growth restriction.

Applications Labelled Budesonide, 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), Clissold, S.P., et al.: Drugs, 28, 485 (1984),

Applications Isopregnanolone-d5 is the isotope labelled analogue of Isopregnanolone (I822200), an derivative used in the preparation of antimicrobial and anti-leukemic steroids. References Shingate, B. et al.: Chem. Biol. Int., 1, 198 (2011); Jegham, H. et al.: Steroids., 77, 1403 (2012);

Applications: An impurity contained in samples of all trans-retinoic acid. References Newton, D., et al.: Cancer Res., 40, 3413 (1980), Curley, R., et al.: Bioorg. Med. Chem. Lett., 2, 1133 (1992), Tanaka, H., et al.: Chem. Pharm. Bull., 43, 356 (1995), Patel, J., et al.: J. Med. Chem., 47, 6716 (2004),

Natural glycoside

Applications 16α-Hydroxy Androsterone is an impurity of Androsterone (A637535), a steroid hormone with weak androgenic activity. Androsterone is a metabolite from Testosterone (T155000) in the liver and is used in doping analysis to detect testosterone misuse. 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)

Applications Labelled Flumethasone (F455000). A glucocorticoid. An anti-inflammatory. References Matuszewski, B, et al.: Anal. Chem., 75, 3019 (2003), Fekete, S., et al.: J. Pharm. Biomed. Anal., 49, 64 (2009),

Applications A metabolite of Stanozolol. References Stein, W.H., et al.: Biochim. Biophys. Acta, 24, 640 (1957).

Yamogenin is a diastereomer of diosgenin, which we have identified as the compound responsible for the anti-hyperlipidemic effect of fenugreek.

Applications Isotope labelled Norethindrone (N676000), a labelled progesterone in combination with acetate used as an oral contraceptive (1,2). It is reasonably anticipated to be a human carcinogen. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants. References 1. Shroff, A. et al.: Anal. Profiles Drug Subst. 1975 ; 4;268-2932. Singh, H. et al.: Am. J .Obstet. Gynecol. 1979 Oct 1;135(3):409-14

Applications A secondary metabolite of Zearalenone (ZON). The macrocyclic lactone Zearalanone used in the synthesis of d,l-Zearalanol. References Hurd, R.N., et al.: J. Med. Chem., 16(5), 543 (1973), Baughman, R., et al.: Science, 297, 787 (2002), Zinedine, A., et al.: Food Chem. Toxicol., 45, 1 (2007), Chailapakul, O., et al.: Food Chem., 109, 876 (2008),

Natural glycoside

Applications A metabolite of 17α-Methyltestosterone (M326400). References Dumasia, M., et al.: Xenobiotica, 11, 323 (1981), Tang, P., et al.: Anal. Biochem., 182, 289 (1989),

Carboxylic acid with additional oxygen functions

3-Keto petromyzonol is a bile alocohol derivative that acts as a sex pheromone in Petromyzon marinus for drug design and biochemical experiments.

Applications Testosterone Cypionate is an anabolic steroid with androgenic properties. Testosterone Cypionate is used for testosterone therapy in males with hypogonadism.Controlled Substance. References Rabkin, J. G., et al.: J. Clin. Psychopharmacol., 19, 19 (1999); Hajjar, R., et al.: J. Clin. Endocrinol. Metab., 82, 3793 (1997); Rhoden, E., et al.: J. Sex Med., 7, 277 (2010);

Formononetin-7-O-gentiobioside is an isoflavonoid glycoside, which is a type of naturally occurring compound often found in plants, specifically in the Fabaceae family. This compound is primarily sourced from various legumes and has been studied for its potential bioactive properties due to its unique chemical structure. The mode of action of formononetin-7-O-gentiobioside involves its interaction with biological pathways, where it may exhibit antioxidant, anti-inflammatory, or estrogen-like activities, similar to other isoflavonoids. These interactions are significant in modulating cellular pathways that can contribute to various physiological effects. Current research into formononetin-7-O-gentiobioside focuses on its applications in pharmacology and nutraceuticals, particularly in the context of developing treatments for diseases such as osteoporosis, cardiovascular disorders, and certain cancers. Its ability to influence estrogen receptors presents a potential therapeutic avenue for hormone-related conditions. However, comprehensive studies are required to fully elucidate its bioactivity and therapeutic potential. Scientists are particularly interested in this compound’s structure-activity relationship to better understand its specific effects and to explore its incorporation into novel therapeutic frameworks.

Applications A phytosterol found in canola oil, rapeseed oil, marine algae and shellfish. This compound has been shown to inhibit sterol Δ24-reductase, an enzyme involved in the mammalian cholesterol biosynthesis pathway. References Bishop, G.J., et al.: Plant Cell Physiol. 42, 114, (2001), Fernandez, C., et al., Biochem. J. 366, 109 (2002),

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),

Applications Bisphenol A (B519495) impurity with estrogenic activity. References Terasaki, M. et al.; Environ. Sci Tech. 39, 3703 (2005); Poskrobko, J. Chromatoogr. A 883, 291 (2000)

Applications 6-OH-Monopropylheptylphthalate is a phthalate metabolite originating from a DPHP (B523500) used in plasticizers to improve chemical and physical properties. References Kasper-Sonnenberg, M. et al.: Int. J. Hyg. Env. Health, 215, 373 (2012); Koch, H. et al.: Int. J. Hyg. Env. Health, 214, 188 (2011);