{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | drug_name = | type = | IUPAC_name = 4-(5-methoxyheptyl)-3,3a,4,5,6,6a-hexahydro-1''H''-pentalen-2-one | image = Cioteronel.svg | image_class = skin-invert-image | width = 250px
<!--Clinical data-->| alt = | caption = | tradename = | MedlinePlus = | licence_EU = | licence_US = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth, topical
<!--Pharmacokinetic data-->| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = <!--Identifiers--> | CAS_number_Ref = | CAS_number = 89672-11-7 | CAS_supplemental = | class = Nonsteroidal antiandrogen | ATC_prefix = None | ATC_suffix = | PubChem = 55994 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 50555 | ChEMBL = 2104105 | UNII = 1RTH95874Z | synonyms = CPC-10997; Cyoctol; X-Andron
<!--Chemical data-->| 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 }}
'''Cioteronel''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}; developmental code '''CPC-10997'''; former tentative brand names '''Cyoctol''', '''X-Andron''') is a nonsteroidal antiandrogen (NSAA) that was never marketed.<ref name="GanellinTriggle1996">{{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 }}</ref><ref name="Lednicer1994">{{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–}}</ref><ref name="TiwariKrishna2005">{{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 }}</ref> 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.<ref name="TiwariKrishna2005" /><ref name="AdisInsight">{{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 }}</ref>
== See also == * Delanterone * Inocoterone * Metogest * Rosterolone * Topilutamide * Topterone * Zanoterone
== References == {{Reflist|2}}
{{Androgen receptor modulators}}
Category:Abandoned drugs Category:Anti-acne preparations Category:Ethers Category:Ketones Category:Nonsteroidal antiandrogens
{{genito-urinary-drug-stub}} {{dermatologic-drug-stub}}