Cioteronel

{{Short description|Chemical compound}}

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| IUPAC_name = 4-(5-methoxyheptyl)-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-one

| image = Cioteronel.svg

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| routes_of_administration = By mouth, topical

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| CAS_number_Ref =

| CAS_number = 89672-11-7

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| class = Nonsteroidal antiandrogen

| ATC_prefix = None

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| PubChem = 55994

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| ChemSpiderID = 50555

| ChEMBL = 2104105

| UNII = 1RTH95874Z

| synonyms = CPC-10997; Cyoctol; X-Andron

| C = 16

| H = 28

| O = 2

| SMILES = CCC(CCCCC1CCC2C1CC(=O)C2)OC

| StdInChI_Ref =

| StdInChI = InChI=1S/C16H28O2/c1-3-15(18-2)7-5-4-6-12-8-9-13-10-14(17)11-16(12)13/h12-13,15-16H,3-11H2,1-2H3

| StdInChIKey_Ref =

| StdInChIKey = KDULJHFMZBRAHO-UHFFFAOYSA-N

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Cioteronel ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}) (developmental code name CPC-10997; former tentative brand names Cyoctol, X-Andron) is a nonsteroidal antiandrogen (NSAA) that was never marketed.{{cite book| vauthors = Ganellin CR, Triggle DJ |title=Dictionary of Pharmacological Agents |url= https://books.google.com/books?id=Z_mfTTIApVEC&pg=PA570 | page = 570 |date=21 November 1996 |publisher=CRC Press |isbn=978-0-412-46630-4 }}{{cite book| first = Daniel | last = Lednicer | name-list-style = vanc |title=The Organic Chemistry of Drug Synthesis|url=https://books.google.com/books?id=Os_OQxrXYPcC&pg=PA11|date=21 November 1994|publisher=John Wiley & Sons|isbn=978-0-471-58959-4|pages=11–}}{{cite journal | vauthors = Tiwari A, Krishna NS, Nanda K, Chugh A | title = Benign prostatic hyperplasia: an insight into current investigational medical therapies | journal = Expert Opinion on Investigational Drugs | volume = 14 | issue = 11 | pages = 1359–72 | date = November 2005 | pmid = 16255676 | doi = 10.1517/13543784.14.11.1359 | s2cid = 25662071 }} It was under development between 1989 and 2001 for the topical treatment of androgenetic alopecia (male pattern baldness), and acne and for the oral treatment of benign prostatic hyperplasia; it reached phase III clinical trials for acne and phase II studies for androgenetic alopecia, but was ultimately discontinued due to poor efficacy.{{cite web | title = Cioteronel | url = https://adisinsight.springer.com/drugs/800003205 | work = Adis Insight | publisher = Springer Nature Switzerland AG | access-date = 2016-11-25 | archive-url = https://web.archive.org/web/20161229031615/https://adisinsight.springer.com/drugs/800003205 | archive-date = 2016-12-29 | url-status = dead }}