565-96-8

Usage

Uses

Used in Pharmaceutical Industry:
11α-Hydroxy-5α-pregnane-3,20-dione is used as an intermediate compound for the synthesis of various steroidal drugs. Its unique structure allows for further chemical modifications, making it a valuable building block in the development of new medications with potential applications in treating hormonal disorders, inflammation, and other conditions related to steroid hormone imbalances.
Used in Research and Development:
In the field of biochemistry and molecular biology, 11α-Hydroxy-5α-pregnane-3,20-dione serves as an important research tool. It can be utilized to study the metabolic pathways of progesterone and other steroid hormones, as well as to investigate the enzymatic activities of Rhizopus nigricans and related fungi. This knowledge can contribute to the understanding of steroid biosynthesis and may lead to the discovery of novel bioactive compounds with therapeutic potential.
Used in Drug Delivery Systems:
Similar to gallotannin, 11α-Hydroxy-5α-pregnane-3,20-dione can also be explored for its potential applications in drug delivery systems. Its steroidal nature may allow for the development of targeted drug delivery platforms, particularly for steroidal drugs, enhancing their bioavailability and therapeutic efficacy.

InChI:InChI=1/C21H32O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13,15-19,24H,4-11H2,1-3H3/t13-,15-,16+,17-,18+,19+,20-,21+/m0/s1

Upstream product

• 566-65-4 dihydroprogesterone 
• 565-91-3 3β,11α-dihydroxy-5α-pregnan-20-one 
• 102291-06-5 3,3,20,20-Bis--5α-pregn-9(11)-en 
• 80-75-1 11-alpha-hydroxyprogesterone 
• 1162-56-7 6-dehydroprogesterone 
• 884878-03-9 11α-acetoxy-3β-hydroxy-5α-pregnan-20-one 
• 128-23-4 pregnanedione 
• 600-52-2 3α,11α-dihydroxy-5β-pregnan-20-one 
• 21063-87-6 11α-hydroxypregna-4,6-diene-3,20-dione 
• 15807-38-2 20,20-ethanediyldioxy-3α-hydroxy-5β-pregnan-11-one 
• 115267-39-5 20,20-ethanediyldioxy-5β-pregnane-3α,11α-diol 

Downstream Products

• 565-91-3 3β,11α-dihydroxy-5α-pregnan-20-one 
• 516-15-4 11-Ketoprogesterone 
• 565-99-1 UC₁₀₁₇ 
• 23930-19-0 Alphaxalone 
• 1064-78-4 3α,11α-dibenzoyloxy-5β-pregnan-20-one 
• 1312468-70-4 3β,11α-dibenzoyloxy-5β-pregnan-20-one 
• 565-92-4 5β-pregnan-3α,11β-diol-20-one 
• 565-98-0 3α,20β-dihydroxy-5β-pregnan-11-one 
• 116377-72-1 11α-(toluene-4-sulfonyloxy)-5β-pregnane-3,20-dione 
• 38398-44-6 3α,11α-dihydroxy-5α-pregnan-20-one 
• 80-75-1 11-alpha-hydroxyprogesterone 
• 2089-06-7 5α-pregnane-3,11,20-trione 
• 1408057-11-3 3,20-dioxo-5β-pregnan-11α-yl pentafluorobenzoate 
• 1408057-14-6 20-oxo-11α-(pentafluorobenzoyl)oxy-5β-pregnan-3α-yl sulfate pyridinium salt 

Relevant academic research and scientific papers

NEUROACTIVE STEROIDS AND METHODS OF PREPARATION

Disclosed are neuroactive steroid anaesthetic agents, methods for their preparation and compositions comprising the same. The invention provides scaled up and/or GMP methods for preparing neuroactive steroids, such as alfaxalone, alfadolone and alfadolone acetate.

Synthesis of new steroidal inhibitors of P-glycoprotein-mediated multidrug resistance and biological evaluation on K562/R7 erythroleukemia cells

A simple route for improving the potency of progesterone as a modulator of P-gp-mediated multidrug resistance was established by esterification or etherification of hydroxylated 5α/β-pregnane-3,20-dione or 5β-cholan-3-one precursors. X-ray crystallography of representative 7α-, 11α-, and 17α-(2′R/S)-O-tetrahydropyranyl ether diastereoisomers revealed different combinations of axial-equatorial configurations of the anomeric oxygen. Substantial stimulation of accumulation and chemosensitization was observed on K562/R7 erythroleukemia cells resistant to doxorubicin, especially using 7α,11α-O-disubstituted derivatives of 5α/β-pregnane-3,20-dione, among which the 5β-H-7α-benzoyloxy-11α-(2′R)-O-tetrahydropyranyl ether 22a revealed promising properties (accumulation index 2.9, IC50 0.5 μM versus 1.2 and 10.6 μM for progesterone), slightly overcoming those of verapamil and cyclosporin A. Several 7α,12α-O-disubstituted derivatives of 5β-cholan-3-one proved even more active, especially the 7α-O-methoxymethyl-12α-benzoate 56 (accumulation index 3.8, IC50 0.2 μM). The panel of modulating effects from different O-substitutions at a same position suggests a structural influence of the substituent completing a simple protection against stimulating effects of hydroxyl groups on P-gp-mediated transport.

Allopregnanolone and pregnanolone analogues modified in the C ring: Synthesis and activity

(25R)-3β-Hydroxy-5α-spirostan-12-one (hecogenin) and 11α-hydroxypregn-4-ene-3,20-dione (11α-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5ξ-pregnanolone (3α-hydroxy-5α- pregnan-20-one and 3α-hydroxy-5β-pregnan-20-one), the principal neurosteroid acting via γ-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABA A receptor. Their biological activity was measured by in vitro test with [3H]flunitrazepam as radioligand in which allopregnanolone and its active analogues stimulated the binding to the GABAA receptor. Analysis of the SAR data suggests dependence of the flunitrazepam binding activity on the hydrophobic-hydrophilic balance of the groups at the C-ring edge rather than on specific interactions between them and the receptor.

Synthesis of deuterium labeled NMDA receptor inhibitor - 20-Oxo-5β-[9,12,12-2H3]pregnan-3α-yl-l- glutamyl 1-ester

20-Oxo-5β-[9,12,12-2H3]pregnan-3α-yl-l- glutamyl 1-ester 11 was synthesized as an internal standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5β-pregnan-3α-yl-l- glutamyl 1-ester 18 and its metabolites, in

NEW STEROID INHIBITORS OF PGP FOR USE FOR INHIBITING MULTIDRUG RESISTANCE

The present invention relates to a compound of formula (I) for its use for reversing or inhibiting multidrug resistance.

Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs

Three analogs of neuroactive steroids were prepared (4-6) in which 1,11- or 11,19-oxygen bridges give a constrained conformation. Their 3D structures were obtained by ab initio calculations and in the case of 3α-hydroxy-11,19-epoxypregn-4-ene-20-one (4), confirmed by X-ray analysis. Biological activity of the synthetic steroids was assayed in vitro using t-[3H]butylbicycloorthobenzoate as radiolabeled ligand for the GABAA receptor. The activity of compound 4 was similar to that of allopregnanolone (1). 1α,11α-Epoxypregnanolone (6) was more active than pregnanolone (2).

Microbial hydroxylation of hydroxyprogesterones and α-glucosidase inhibition activity of their metabolites

Microbial transformation of 11α-hydroxyprogesterone (1) with Cunninghamella elegans, Gibberella fujikuroi, Fusarium lini, and Candida albicans yielded 11α,15α,16α-trihydroxypregn-4-ene-3,20-dione (3), 11α-hydroxy-5α-pregnane-3,20-dione (4), 6β,11α- dihydroxypregn-4-ene-3,20-dione(5), 11α-hydroxypregna-1,4-diene-3,20-dione (6), 11α,17β-dihydroxyandrost-4-en-3-one (7), and 11α,15α-dihydroxypregn-4-ene-3,20-dione (8). On the other hand, microbial transformation of 17α-hydroxyprogesterone (2) with Cunninghamella elegans and Fusarium Uni yielded 11α,17α- dihydroxypregn-4-ene-3,20-dione (9), and 17α-hydroxypregna-1,4-diene-3,20- dione (10). The structures of the metabolites 3-10 were deduced on the basis of spectroscopic methods. Compound 3 was identified as a new metabolite, which exhibited a promising inhibitory activity against the α-glucosidase enzyme.