516-58-5

Usage

Uses

Used in Pharmaceutical Industry:
Allopregnan-20beta-ol-3-one is used as a pharmaceutical compound for its potential role in modulating the maturation and secretory activity of the uterine endothelium. It is also being investigated for its suppressive effects on ovulation and its implications in the etiology of breast cancer.
Used in Research and Development:
In the field of research and development, allopregnan-20beta-ol-3-one serves as a valuable compound for studying the effects of steroid hormones on various biological processes, including reproductive health and cancer development. Its unique structure and properties make it a promising candidate for further investigation and potential therapeutic applications.

Upstream product

• 516-52-9 isofuntumidine 
• 1011735-38-8 20(R)-formyloxy-5αH-pregnan-3-one 
• 18003-79-7 3,3-dimethoxy-5α-pregnan-20-one 
• 474-45-3 (3α,5α)-3-aminopregnan-20-one 
• 6057-94-9 3β,20β_F-diacetoxy-5α-pregnane 
• 6003-19-6 acetic acid-(3β-hydroxy-5α-pregnanyl-(20β_F)-ester) 
• 566-58-5 5α-pregnane-3α,20α-diol 
• 516-53-0 (20R)-5α-Pregnandiol-(3β.20) 
• 95564-96-8 3.3-Dimethoxy-20β-hydroxy-5α-pregnan 
• 566-65-4 dihydroprogesterone 
• 5888-07-3 20β_F-acetoxy-5α-pregnan-3-one 
• 432552-68-6 (20R)-3-oxo-5α-pregnan-20-yl benzoate 

Downstream Products

• 846-46-8 androstanedione 
• 566-65-4 dihydroprogesterone 
• 432552-70-0 (20R)-3,3-difluoro-5α-pregnan-20-yl benzoate 

Relevant academic research and scientific papers

Substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase

In this study, we examined the substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase (AKR1C5), which plays a role in the termination of pregnancy by progesterone inactivation. AKR1C5 moderately reduced the 3-keto group of only 5α-dihydrosteroids with 17β- or 20α/β-hydroxy group among 3-ketosteroids. In contrast, the enzyme reversibly and efficiently catalyzed the reduction of various 17- and 20-ketosteroids, including estrogen precursors (dehydroepiandrosterone, estrone and 5α-androstan-3β- ol-17-one) and tocolytic 5β-pregnane-3,20- dione. In addition to the progesterone inactivation, the formation of estrogens and metabolism of the tocolytic steroid by AKR1C5 may be related to its role in rabbit parturition. AKR1C5 also reduced various non-steroidal carbonyl compounds, including isatin, an antagonist of the C-type natriuretic peptide receptor, and 4-oxo-2-nonenal, suggesting its roles in controlling the bioactive isatin and detoxification of cytotoxic aldehydes. AKR1C5 was potently and competitively inhibited by flavonoids such as kaempferol and quercetin, suggesting that its activity is affected by ingested flavonoids.

An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one

Lipase-catalyzed transesterification of the 20 hydroxyl group in a series of pregnanes afforded novel 20-ethyl succinates that are not possible to prepare following the traditional synthetic methods. The reaction is stereoselective. The enzyme reacts selectively with the 20β epimers therefore only the 20β-succinyloxy derivatives are obtained. These compounds are obtained in variable yield, depending on the substitution in the ring A. The enzymatic approach allowed, for the first time, the synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one, novel compound useful as a precursor of steroid-protein conjugates.