{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,12]],"date-time":"2026-03-12T04:40:07Z","timestamp":1773290407747,"version":"3.50.1"},"reference-count":14,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2021,9,19]],"date-time":"2021-09-19T00:00:00Z","timestamp":1632009600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2021,11,15]]},"abstract":"<jats:sec>\n                    <jats:title>Rationale:<\/jats:title>\n                    <jats:p>\n                      Chlorphenesin is an approved biocide frequently used in cosmetics, and its carbamate ester is an approved skeletal muscle relaxant in certain countries for the treatment of discomfort related to skeletal muscle trauma and inflammation. A major urinary metabolite is 4\u2010chlorophenoxy acetic acid (4\u2010CPA), also known as\n                      <jats:italic>para<\/jats:italic>\n                      \u2010chlorophenoxyacetate, which is also employed as a target analyte in sports drug testing to detect the use of the prohibited nootropic stimulant meclofenoxate. To distinguish between 4\u2010CPA resulting from chlorphenesin, chlorphenesin carbamate, and meclofenoxate, urinary metabolite profiles of chlorphenesin after legitimate use were investigated.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Methods:<\/jats:title>\n                    <jats:p>Human administration studies with commercially available sunscreen containing 0.25% by weight of chlorphenesin were conducted. Six study participants dermally applied 8\u00a0g of sunscreen and collected urine samples before and up to 7\u00a0days after application. Another set of six study participants applied 8\u00a0g of sunscreen on three consecutive days, and urine samples were also taken for up to 5\u00a0days after the last dosing. Urine specimens were analyzed using liquid chromatography\u2010high resolution (tandem) mass spectrometry, and urinary metabolites were identified in accordance with literature data by accurate mass analysis of respective precursor and characteristic product ions.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Results:<\/jats:title>\n                    <jats:p>In accordance with literature data, chlorphenesin yielded the characteristic urinary metabolites, chlorphenesin glucuronide, chlorphenesin sulfate, and 3\u2010(4\u2010chlorophenoxy)\u20102\u2010hydroxypropanoic acid (4\u2010CPP), as well as the common metabolite 4\u2010CPA. 4\u2010CPA and 4\u2010CPP were observed at similar abundances, with urinary concentrations of 4\u2010CPA reaching up to ~1500 and 2300\u2009ng\/mL after single and multiple sunscreen applications, respectively.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Conclusion:<\/jats:title>\n                    <jats:p>4\u2010CPA is a common metabolite of meclofenoxate, chlorphenesin, and chlorphenesin carbamate. Monitoring the diagnostic urinary metabolites of chlorphenesin provides conclusive supporting evidence of whether chlorphenesin or the prohibited nootropic meclofenoxate was administered.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.9183","type":"journal-article","created":{"date-parts":[[2021,8,25]],"date-time":"2021-08-25T05:38:32Z","timestamp":1629869912000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Chromatographic\u2010mass spectrometric analysis of the urinary metabolite profile of chlorphenesin observed after dermal application of chlorphenesin\u2010containing sunscreen"],"prefix":"10.1002","volume":"35","author":[{"given":"Ana","family":"Rubio","sequence":"first","affiliation":[{"name":"Center for Preventive Doping Research, Institute of Biochemistry German Sport University Cologne  Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christian","family":"G\u00f6rgens","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research, Institute of Biochemistry German Sport University Cologne  Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oliver","family":"Krug","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research, Institute of Biochemistry German Sport University Cologne  Cologne Germany"},{"name":"European Monitoring Center for Emerging Doping Agents (EuMoCEDA)  Cologne\/Bonn Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masato","family":"Okano","sequence":"additional","affiliation":[{"name":"Anti\u2010Doping Laboratory, LSI Medience Corporation  Tokyo Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Matthew","family":"Fedoruk","sequence":"additional","affiliation":[{"name":"United States Anti\u2010Doping Agency (USADA)  Colorado Springs Colorado"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brian","family":"Ahrens","sequence":"additional","affiliation":[{"name":"UCLA Olympic Analytical Laboratory, Department of Pathology and Laboratory Medicine David Geffen School of Medicine  Los Angeles California"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hans","family":"Geyer","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research, Institute of Biochemistry German Sport University Cologne  Cologne Germany"},{"name":"European Monitoring Center for Emerging Doping Agents (EuMoCEDA)  Cologne\/Bonn Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1535-6451","authenticated-orcid":false,"given":"Mario","family":"Thevis","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research, Institute of Biochemistry German Sport University Cologne  Cologne Germany"},{"name":"European Monitoring Center for Emerging Doping Agents (EuMoCEDA)  Cologne\/Bonn Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,9,19]]},"reference":[{"key":"e_1_2_7_2_1","first-page":"399","volume-title":"Recent Advances in Doping Analysis","author":"Guddat S","year":"2006"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1093\/chromsci\/48.5.353"},{"key":"e_1_2_7_4_1","unstructured":"World Anti\u2010Doping Agency.Meclofenoxate.2006.https:\/\/www.wada\u2010ama.org\/sites\/default\/files\/resources\/files\/tl01_meclofenoxate_eng_2021.pdf(03\u201008\u20102021)"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23071571"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1177\/1091581814526893"},{"key":"e_1_2_7_7_1","first-page":"E50","article-title":"Skin safety and health prevention: An overview of chemicals in cosmetic products","volume":"60","author":"Panico A","year":"2019","journal-title":"J Prev Med Hyg"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(69)90347-5"},{"key":"e_1_2_7_9_1","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/S0022-3565(25)26848-3","article-title":"The metabolism of Chlorphenesin carbamate","volume":"145","author":"Buhler DR","year":"1964","journal-title":"J Pharmacol Exp Ther"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2016.09.015"},{"key":"e_1_2_7_11_1","unstructured":"World Anti\u2010Doping Agency.MINIMUM CRITERIA FOR CHROMATOGRAPHIC\u2010MASS SPECTROMETRIC CONFIRMATION OF THE IDENTITY OF ANALYTES FOR DOPING CONTROL PURPOSES.2021.https:\/\/www.wada-ama.org\/sites\/default\/files\/resources\/files\/td2021idcr_final_eng_0.pdf(10\u201008\u20102021)"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-4347(00)00251-6"},{"key":"e_1_2_7_13_1","unstructured":"World 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