{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T17:50:35Z","timestamp":1792000235482,"version":"4.4.0"},"reference-count":18,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2025,11,18]],"date-time":"2025-11-18T00:00:00Z","timestamp":1763424000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,11,18]],"date-time":"2025-11-18T00:00:00Z","timestamp":1763424000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP22K06571"],"award-info":[{"award-number":["JP22K06571"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2025,12,11]]},"abstract":"<jats:p>\n                    Abiraterone (Abi) acetate, an anticancer drug, produces metabolites in the serum of patients with prostate cancer. Three unknown metabolites of Abi are previously discovered and the structures of two of these compounds are determined by comparing their LC\u2010based retention times with those of synthesized compounds. However, the structure of the third metabolite is not identified. Herein, two new Abi derivatives, 5\u03b1\u2010\u0394\n                    <jats:sup>1<\/jats:sup>\n                    \u2010abiraterone (5\u03b1\u2010D1A) and 5\u03b2\u2010\u0394\n                    <jats:sup>1<\/jats:sup>\n                    \u2010abiraterone (5\u03b2\u2010D1A), with a molecular weight of 348, are successfully synthesized as candidates for the third unknown metabolite. 5\u03b2\u2010D1A is confirmed as this third metabolite based on its retention time in the extracted ion chromatogram. The metabolic pathway may have formed 5\u03b2\u2010D1A rather than 5\u03b1\u2010D1A because of the higher activity of steroid 5\u03b2\u2010reductase compared with that of 5\u03b1\u2010reductase. These findings are expected to lead to the discovery of new metabolic pathways.\n                  <\/jats:p>","DOI":"10.1002\/cbic.202500675","type":"journal-article","created":{"date-parts":[[2025,11,18]],"date-time":"2025-11-18T10:37:47Z","timestamp":1763462267000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis of the Abiraterone Derivatives 5\u03b1\u2010 and 5\u03b2\u2010\u0394\n                    <sup>1<\/sup>\n                    \u2010Abiraterone and Structural Determination of an Unknown Metabolite in Human Serum Derived from Oral Abiraterone Acetate"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1532-5249","authenticated-orcid":false,"given":"Noboru","family":"Hayama","sequence":"first","affiliation":[{"name":"Faculty of Pharmacy Osaka Medical and Pharmaceutical University  4\u201020\u20101 Nasahara Takatsuki Osaka 569\u20131094 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Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6475-048X","authenticated-orcid":false,"given":"Yoshihide","family":"Usami","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy Osaka Medical and Pharmaceutical University  4\u201020\u20101 Nasahara Takatsuki Osaka 569\u20131094 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