571-24-4

Usage

Uses

Used in Pharmaceutical Industry:
17α-Hydroxy-5α-androstan-3-one is used as a pharmaceutical compound for its testosterone-like properties. It is particularly useful in the development of treatments for conditions related to hormonal imbalances or androgen deficiency, as it can help maintain cell conformation in epithelial cells, which is essential for proper cell function and overall health.
Used in Research and Development:
In the field of research and development, 17α-Hydroxy-5α-androstan-3-one serves as an important compound for studying the effects of testosterone analogs on various biological processes. Its structural similarities to testosterone make it a valuable tool for understanding the mechanisms of action and potential therapeutic applications of similar compounds.
Used in Sports Medicine:
17α-Hydroxy-5α-androstan-3-one may also be used in sports medicine as a potential therapeutic agent for conditions related to muscle wasting or recovery, given its anabolic properties similar to testosterone. However, it is essential to note that the use of such compounds in sports should be strictly regulated and adhere to anti-doping guidelines to ensure fair competition and athlete safety.

Upstream product

• 103133-50-2 3-oxo-5α-androstan-17α-yl cyclohexanecarboxylate 
• 481-30-1 epitestosterone 
• 17291-35-9 3-Oxo-5α-androstan-17β-ol-toluol-p-sulfonat 
• 71120-50-8 Pyridine-3-sulfonic acid (5S,10S,13S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester 
• 481-30-1 epitestosterone 
• 100428-85-1 17α-hydroxyandrost-5-en-3β-yl 3-acetate 
• 40768-04-5 3β-hydroxyandrost-5-en-17α-yl benzoate 
• 150054-83-4 3β-hydroxy-5α-androstan-17α-yl cyclohexanecarboxylate 
• 40768-03-4 androst-5-ene-3β,17α-diyl 3-acetate 17-benzoate 
• 1639-43-6 androstenediol-3-acetate 
• 853-23-6 prasterone acetate 
• 36025-82-8 3-oxoandrost-4-en-17α-yl benzoate 
• 1259-22-9 5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate 

Downstream Products

• 64919-12-6 dihydrotestosterone p-chlorophenoxyisobutyrate 
• 88674-60-6 2-(4-Chloro-phenoxy)-2-methyl-propionic acid (5S,10R,13S,17S)-3-[2-(4-chloro-phenoxy)-2-methyl-propionyloxy]-10,13-dimethyl-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 855-22-1 dihydrotestosterone propionate 
• 88674-61-7 Propionic acid (5S,10R,13S,17S)-10,13-dimethyl-17-propionyloxy-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 10148-98-8 (3S,5S,8R,9S,10S,13S,14S,17S)-3-ethynyl-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol 
• 17006-60-9 3α-ethynyl-3β-hydroxyandrostan-17-one 
• 65-06-5 17-Hydroxy-androst-1-en-3-on 

Relevant academic research and scientific papers

Identification of steroidal derivatives inhibiting the transformations of allopregnanolone and estradiol by 17β-hydroxysteroid dehydrogenase type 10

17β-Hydroxysteroid dehydrogenase type 10 (17β-HSD10) is a mitochondrial enzyme known for its potential role in Alzheimer's Disease (AD). 17β-HSD10, by its oxidative activity, could decrease the concentration of two important neurosteroids, allopregnanolone (ALLOP) and 17β-estradiol (E2), respectively preventing their neurogenesis and neuroprotective effects. Since the inhibition of 17β-HSD10 could lead to a new treatment for AD, we developed two biological assays using labeled ALLOP or E2 as substrates to measure the inhibitory activity of compounds against pure 17β-HSD10 protein. After the optimization of different parameters (time, concentration of enzyme, substrate and cofactor), analogs of the first reported steroidal inhibitor of 17β-HSD10 in intact cells were screened to determine their inhibitory potency for the ALLOP or the E2 oxidation. One compound, androstane derivative 5, possesses the best dual inhibition against both transformations (ALLOP, IC50 = 235 μM and E2, IC50 = 610 μM). Some compounds are dual inhibitors to a lesser extent, and others seem selective for one of the transformations in particular. By developing two reliable assays and by identifying a first generation of steroidal inhibitors of pure 17β-HSD10, this preliminary study opens the door to new and more potent inhibitors.

Synthesis of 17β-hydroxysteroid dehydrogenase type 10 steroidal inhibitors: Selectivity, metabolic stability and enhanced potency

17beta-Hydroxysteroid dehydrogenase type 10 (17β-HSD10) is the only mitochondrial member of 17β-HSD family. This enzyme can oxidize estradiol (E2) into estrone (E1), thus reducing concentration of this neuroprotective steroid. Since 17β-HSD10 possesses properties that suggest a possible role in Alzheimer's disease, its inhibition appears to be a therapeutic strategy. After we identified the androsterone (ADT) derivative 1 as a first steroidal inhibitor of 17β-HSD10, new analogs were synthesized to increase the metabolic stability, to improve the selectivity of inhibition over 17β-HSD3 and to optimize the inhibitory potency. From six D-ring derivatives of 1 (17-C[dbnd]O), two compounds (17β-H/17α-OH and 17β-OH/17α-C[tbnd]CH) were more metabolically stable and did not inhibit the 17β-HSD3. Moreover, solid phase synthesis was used to extend the molecular diversity on the 3β-piperazinylmethyl group of the steroid base core. Eight over 120 new derivatives were more potent inhibitors than 1 for the transformation of E2 to E1, with the 4-(4-trifluoromethyl-3-methoxybenzyl)piperazin-1-ylmethyl-ADT (D-3,7) being 16 times more potent (IC50 = 0.14 μM). Finally, D-ring modification of D-3,7 provided 17β-OH/17α-C[tbnd]CH derivative 25 and 17β-H/17α-OH derivative 26, which were more potent inhibitor than 1 (1.8 and 2.4 times, respectively).

Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN

A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also shown that nitrogenated substrates such as hydrazones, N-tosylhydrazones, and ketimines reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.

Steroidal isomers with uniform mass spectra of their per-TMS derivatives: Synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols

In human sports doping control analysis most of the steroids are analyzed after enzymatic hydrolysis of the glucuronides as per-trimethylsilyl (TMS) derivatives applying gas chromatography-mass spectrometry (GC-MS). According to the recommendations of the World Anti-Doping Agency the identification of analytes should be based on retention time and on mass spectrometric characterization. This study shows that the bis-TMS derivatives of 16 specific C19 steroids, namely the stereoisomers of 5ξ-androst-1-ene-3ξ,17ξ-diol (8 isomers), androst-4-ene-3ξ,17ξ-diol (4 isomers), and 17ξ-hydroxy-5ξ-androstan-3-one (4 isomers), reveal very similar mass spectra. As a rule, when taking the retention times, which are provided as Kovac indices for all these isomers, into account, a restriction to two or three possible isomers is possible. Reliable identification should additionally include a comparison of the retention times of the analytes with the reference compounds measured concomitantly. In some cases standard addition may be appropriate. Due to the limited availability, the above mentioned isomers were synthesized by reduction of the corresponding α,β-unsaturated oxo steroids either with K-Selectride or by catalytic hydrogenation (Pd/C as catalyst). The products of the reactions were identified by means of nuclear magnetic resonance (NMR) characterization and by further reduction to the corresponding 5ξ-androstane-3ξ,17ξ-diols and GC-MS comparison with commercially available reference standards.

PREPARATION OF UNLABELLED AND 3H>-LABELLED EPITESTOSTERONE AND ITS METABOLITES

Cold as well as 3H>-labelled substrates and metabolites IX-XI, XV, XVI, XX-XXII, XXIV, XXV and XXVIII were prepared by catalytic hydrogenation of epitestosterone (VIII) and Λ1-dehydroepitestosterone (XIII).The key step in the preparation of compound XXVIII was reaction of 3β-tosylates XXVI and XXX with potassium nitrite in dimethyl sulfoxide.

Distinction Between 17-Epimeric Hydroxy Steroids of the 3,17-Dioxygenated Androstane Series by Chemical Ionization

The distinction between 17-epimeric 3,17-dioxygenated hydroxyandrostanes has been made by comparison of both their methane or ammonia positive and OH- negative chemical ionization (CI) mass spectra.In the methane or ammonia positive CI, the 17α-configuration in the eight stereoisomeric 5ξ-androstane-3ξ,17ξ-diols can be determined by the relative abundances of the ion +.In the ammonia CI spectra, the ion + possesses only a low abundance, but a comparison of the relative rates of the loss of water v. the loss of ammonia from + in the second field -free region allows a clear distinction to be made between the 17α- and 17β-series.In the OH- negative CI mass spectra, the 5ξ-androstane-3-one-17ξ-ols produce an intense ion - in the 17α-series only.