Steroids

Protogracillin is a steroidal saponin isolated from Dioscorea zingiberensis Wright (DZW) which may inhibit platelet aggregation (PAG) and thrombosis.

Hydrocortisone is a synthetic glucocorticoid that aids in metabolism, immunity, and inflammation control.

Applications Labelled 3,4-Methylenedioxymethamphetamine (MDMA), an Entactogen; It is the N-methyl derivative of MDA. The (S)-form of MDMA possesses more potent CNS activity than the (R) form of MDMA.MDMA is controlled substance (hallucinogen). References Ellison, G., et al.: Science, 201, 276 (1978); Escubedo, E., et al.: J. Pharmacol. Exp. Ther., 315, 658 (2005); Fayuk, D., et al.: J. Physiol., 566, 759 (2005), Tretter, L., et al.: Neurochem. Int., 50, 139 (2007);

Natural alkaloid

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),

Timosaponin A1 is a coprostane type steroidal saponin found in Rhizoma Anemarrhenae.

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

Applications A synthetic derivative of Dehydroepiandrosterone. The reduced androgenicity of Fluasterone may obviate toxicities associated with the androgenicity of the parent compound. Antitumor agent. Used in clinical trials for prostate cancer prevention. References Bentley, P., et al.: Food Chem. Toxicol., 31, 857 (1993), Rao, K., et al.: Cancer Res., 59, 3084 (1999), Masuzaki, H., et al.: Science, 294, 2166 (2001), Osawa, E., et al.: Life Sci., 70, 2623 (2002),

Lactone

Natural alkaloid

Applications Labelled form of Meloxicam. Preferential cyclooxygenase (COX-2) inhibitor. Used as an anti-inflammatory. 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 Hawkey, C., et al.: Br. J. Rheumatol., 35, Suppl. 1, 1 (1996), Fleischmann, R., et al.: Expert Opin. Pharmacother., 3, 1501 (2002),

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);

8'-Hydroxyformononetin is a phytoestrogen compound, which is derived from plant sources, particularly from legumes, including red clover and soy. As a naturally occurring isoflavone, it falls within the class of flavonoids, a group of polyphenolic compounds with varied biological activities. Its mode of action primarily involves binding to estrogen receptors, where it can mimic or modulate the action of estrogen in the body. This interaction can result in either estrogenic or anti-estrogenic effects, depending on the presence of endogenous estrogen and other factors within the target tissues. The compound has garnered significant interest due to its potential applications in addressing hormone-related conditions. It is being studied for its roles in managing menopausal symptoms, osteoporosis, and potentially as part of cancer therapies, due to its ability to influence estrogen receptor pathways. Additionally, its antioxidant properties add another layer of functionality, suggesting possible use in preventing oxidative stress-related conditions. Research continues to explore its efficacy and safety, aiming to elucidate the mechanisms underlying its biological effects and therapeutic potential.

3-O-Acetyl-20-Hydroxyecdysone, a steroid extracted from the roots of Cyanotis arachnoidea C.B.Clark, is characterized by its unique structural modifications.

Applications [18O] Cholesterol can be used as a practical tracer for studies of cholesterol metabolism in humans. References Hudgins, L.C., et al.: Biomed. Environ. Mass Spect., 17, 463 (1988),

Applications Dihydro Dutasteride is an impurity arose during the process development of Dutasteride (D735000). References Solomons, W., et al.: J. Pharma. Sci., 63, 19 (1974), Rasmusson, G., et al.: J. Med. Chem., 29, 2298 (1986),

Applications 18-Hydroxycortisol is a derivative of Cortisol (H714615), frequently referred to as the “stress hormone”, is released into the bloodstream during periods of stress. Cortisol also has effects on enhancing memory with regards to emotions during stressful events. References Buchanan, T., et al.: Psychoneuroendocrino, 26, 307 (2001); Stark, R., et al.: Neuroimage, 32, 1290 (2006)

Applications 5α-Androstenone is a volatile steroid found in human perspiration, boar saliva, truffles, and celery. It was also identified as the first mammalian pheromone. References Wysocki, C.J., et al.: P. Natl. Acad. Sci. USA, 86, 7976 (1989); Dorries, K.M., et al.: Brain Behav. Evol., 49, 53 (1997)

Stability Hygroscopic Applications (3α,5β,7α)-7-Hydroxy-3-(sulfooxy)-cholan-24-oic Acid is the 3-monosulfate derivative of chenodeoxycholic acid (C291900), a major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. References Haslewood, E.S., et al.: Biochem. J., 155, 401 (1976); Parmentier, G., et al.: Steroids., 30, 583 (1977);

Halcinonide is a potent topical corticosteroid, which is a synthetically derived compound from hydrocortisone. It operates by penetrating the cell membranes and binding to cytoplasmic receptors, leading to a subsequent translocation to the nucleus where it modulates genetic expression. This action results in diminished synthesis of pro-inflammatory cytokines, thereby exerting strong anti-inflammatory, antipruritic, and vasoconstrictive effects. Halcinonide is primarily utilized for the management of various dermatological conditions characterized by inflammation and itching. It is effective against disorders such as eczema, psoriasis, and dermatitis, where control of the inflammatory response is crucial. Due to its potency, its use is reserved for conditions that do not respond adequately to less potent corticosteroids. Application involves a topical route, allowing for direct delivery to affected areas, minimizing systemic exposure. However, its use must be judiciously controlled to mitigate potential side effects such as skin atrophy or systemic absorption, especially in long-term treatment scenarios or under occlusive dressing. Thus, Halcinonide serves as an integral tool in the dermatological therapeutic arsenal.

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),

Sodium taurodeoxylate, a bile salt, is used as an anionic detergent for isolating membrane proteins and inhibits inflammation.

Lactone

Convallatoxin is a natural product.

Applications Used in the preparation of 16β-Hydroxy Stanozolol (H953550), a Stanozolol (S684500) metabolite. References Schaenzer, W. et al.; J. Steroid. Biochem. 36, 153 (1990)

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

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue. Bufotalin has anti-cancer activity, it can induce apoptosis in Hep 3B cells, and caspase-8 inhibitor (Z-IETD) or wide-ranging caspase inhibitor (Z-VAD) significantly suppresses the bufotalin-induced apoptosis. Bufotalin is a powerful sensitizer of death receptor-induced apoptosis in cancer cells, it promotes death receptor-mediated cell death, especially TRAIL-induced apoptosis, through activation of caspase-3 and PARP-1.

7α-Hydroxy-4-cholesten-3-one is a PXR agonist that can be used to study diseases associated with defects in bile acid biosynthesis.

Applications 11-Dehydrocorticosterone is a precursor to corticosterone (C695700), converted by 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) which plays a role in glucocorticoid-induced insulin resistance. References Morgan, S. et al.: Diabetes, 58, 2506 (2009);

Digoxigenin is a cardiac glycoside drug for treating heart failure and other heart conditions.

Applications It 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),

Pregnenolone monosulfate (3β-Hydroxy-5-pregnen-20-one monosulfate) is a potent nootropic steroid used in the study of neuroticism and depression.

Applications Protected Estradiol. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants. References Miilunpohja, M., et al.: J. Steroid Biochem. Mol. Biol., 100, 59 (2006), Ikonomou, M., et al.: Environ. Toxicol. Chem., 27, 243 (2008),