548-97-0

Usage

Uses

Used in Pharmaceutical Industry:
6,17,21-trihydroxypregn-4-ene-3,20-dione is used as a therapeutic agent for the treatment of conditions such as hypertension, metabolic syndrome, and other disorders related to dysregulated cortisol and aldosterone levels. Its ability to inhibit 11β-hydroxysteroid dehydrogenase type 2 makes it a promising candidate for managing these conditions and improving overall health outcomes.

Upstream product

• 7444-96-4 6β,21-diacetoxy-17-hydroxy-pregn-4-ene-3,20-dione 
• 152-58-9 Cortexolone 
• 55388-56-2 6β,17,21-trihydroxypregn-4-ene-3,20-dione 17,21-acetonide 
• 55388-55-1 17,21-dihydroxy-3-methoxypregna-3,5-dien-20-one 17,21-acetonide 
• 1474-10-8 3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate 
• 897047-90-4 6β,21-diacetoxy-5,17-dihydroxy-5α-pregnane-3,20-dione 
• 1167-48-2 3β,17α,21-trihydroxypregn-5-en-20-one 
• 3517-42-8 17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one 
• 32603-90-0 21-acetoxy-5,6α-epoxy-3β,17-dihydroxy-5α-pregnan-20-one 
• 640-87-9 cortexolone 21-acetate 
• 913-44-0 21-acetoxy-17α-hydroxy-3,3-ethylenedioxypregn-5-ene-20-one 
• 145013-91-8 21-acetoxy-3,3-ethanediyldioxy-5,6ξ-epoxy-17-hydroxy-5ξ-pregnan-20-one 

Downstream Products

• 2243-06-3 androst-4-ene-3,6,17-trione 

Relevant academic research and scientific papers

Structure–function analysis for the hydroxylation of Δ4 C21-steroids by the myxobacterial CYP260B1

Myxobacterial CYP260B1 from Sorangium cellulosum was heterologously expressed in Escherichia coli and purified. The in?vitro conversion of a small focused substrate library comprised of Δ4 C21-steroids and steroidal drugs using surrogate bovine redox partners shows that CYP260B1 is a novel steroid hydroxylase. CYP260B1 performs the regio- and stereoselective hydroxylation of the glucocorticoid cortodoxone (RSS) to produce 6β-OH-RSS. The substrate-free crystal structure of CYP260B1 (PDB 5HIW) was resolved. Docking of the tested ligands into the crystal structure suggested that the C17 hydroxy moiety and the presence of either a keto or a hydroxy group at C11 determine the selectivity of hydroxylation.

Novel reduction and hydroxylation products formed by Aspergillus fumigatus from Reichstein's Substance S

Fermentation of Reichstein's Substance S with Aspergillus fumigatus (AM- 21) under aerobic conditions yielded 17α, 21-dihydroxy-5α-pregn-1-ene- 3,20-dione, 17α,20α,21-trihydroxy-5α-pregn-1-en-3-one, 6β,17α,21- trihydroxypregn-4-en-3,20-dione, 15β,17α,21-trihydroxy-5α-pregnane-3,20- dione, and 15β,17α,20α,21-tetrahydroxy-5α-pregn-1-en-3-one. Each microbial metabolite was characterized by spectroscopic methods, including 13C NMR chemical shifts.

Synthesis and characterization of the 6α- and 6β-hydroxylated derivatives of corticosterone, 11-dehydrocorticosterone, and 11-deoxycortisol

This report describes the synthesis of 6α,17,21- and 6β,17,21-trihydroxypregn-4-ene-3,20-dione, 6α,7,21- and 6β,11β,21-trihydroxypregn-4-ene-3,20-dione, and - for the first time - that of 6α,21- and 6β,21-dihydroxypregn-4-ene-3,11,20-trione. The former four compounds were prepared by 6-hydroxylation of 17,21-dihydroxypregn-4-ene-3,20-dione and 11β,21-dihydroxypregn-4-ene-3,20-dione, respectively. This was achieved by autoxidation or by oxidation with 3-chloroperbenzoic acid, of the 3-methoxypregna-3,5-dienes of the latter two steroids. The yield of the 6β-hydroxylated steroids, but not of their corresponding 6α-epimers, was higher using autoxidation than the peracid. The two 6-hydroxylated pregnenetriones were prepared from 6α,21-diacetoxy-11β-hydroxypregn-4-ene-3,20-dione and 6β,21-diacetoxy-11β-hydroxypregn-4-ene-3,20-dione, respectively, by oxidation with pyridinium chlorochromate. The above-mentioned six steroids were identified and characterized by nuclear magnetic resonance, infrared, ultraviolet, high performance liquid chromatography, gas chromatography, and mass spectrometry. Keywords: synthesis; corticosteroids; 6-hydroxylation; NMR; HPLC; GC/MS.