title: Biotransformation studies of prednisone using human intestinal bacteria Part II: Anaerobic incubation and docking studies.
abstract: Anaerobic incubation of prednisone 1 with human intestinal bacteria (HIB) afforded nine metabolites: 5beta-androst-1-ene-3,11,17-trione 3, 3alpha-hydroxy-5alpha-androstane-11,17-dione 4, 3beta,17alpha,20-trihydroxy-5alpha-pregnan-11-one 5, 3alpha,17alpha-dihydroxy-5alpha-pregnane-11,20-dione 6, 3alpha,17alpha-dihydroxy-5beta-pregnane-11,20-dione 7, 3beta,17beta-dihydroxy-5alpha-androstan-11-one 8beta, 3beta,17alpha-dihydroxy-5alpha-androstan-11-one 8alpha, 3alpha,17beta-dihydroxy-5alpha-androstan-11-one 9beta, and 3alpha,17alpha-dihydroxy-5alpha-androstan-11-one 9alpha. The structures of these metabolites (3-9) were elucidated using several spectroscopic techniques. Computer-aided prediction of potential biological activities of the isolated prednisone metabolites (3-9) revealed potential inhibition of prostaglandin E2 9-ketoreductase (PGE2 9-KR). Docking studies applied to PGE2 9-KR allowed recommendation of the metabolites 4, 8beta, and 8alpha for further pharmacological study as PGE2 9-KR inhibitors.
authors.affiliation: Department of Pharmaceutical Medicinal Chemistry, Assiut University, Assiut, Egypt.
authors.forename: Mohamed M
authors.initials: MM
authors.lastname: Al-Sanea
authors.forename: Atef A
authors.initials: AA
authors.lastname: Abdel-Hafez
authors.forename: Farghaly A
authors.initials: FA
authors.lastname: Omar
authors.forename: Adel F
authors.initials: AF
authors.lastname: Youssef
mesh_terms: D000693:Anaerobiosis; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000378:metabolism* / Q000493:pharmacokinetics; D001419:Bacteria / Q000254:growth & development / Q000378:metabolism*; D001711:Biotransformation; D003198:Computer Simulation; D006801:Humans; D006911:Hydroxyprostaglandin Dehydrogenases / Q000037:antagonists & inhibitors / Q000378:metabolism; D007422:Intestines / Q000382:microbiology*; D011241:Prednisone / Q000737:chemistry / Q000378:metabolism* / Q000493:pharmacokinetics; D013057:Spectrum Analysis
chemical_list: D000893:Anti-Inflammatory Agents; D006911:Hydroxyprostaglandin Dehydrogenases; C035858:prostaglandin-E2 9-reductase; D011241:Prednisone