{{위키데이터 속성 추적}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457114462
| image = Ketoconazole enantiomers.svg
| width = 250
| alt =
| caption = (2''R'',4''S'')-(+)-케토코나졸 (위)<br />(2''S'',4''R'')-(−)-케토코나졸 (아래)
| image2 = (2R,4S)-(+)-ketoconazole-from-xtal-3D-bs-17.png
| alt2 = 
| caption2 = (2''R'',4''S'')-(+)-케토코나졸의 [[공-막대 모형]]
| chirality = [[라세미 혼합물]]<ref name="AR">{{웹 인용|title=Assessment report: Ketoconazole HRA|url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003906/WC500181493.pdf |publisher=[[European Medicines Agency]] (EMA) |access-date=26 August 2016|url-status=live|archive-url=https://web.archive.org/web/20160827011824/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003906/WC500181493.pdf|archive-date=27 August 2016}}</ref><ref name = "Arakak">{{저널 인용| vauthors = Arakaki R, Welles B | title = Ketoconazole enantiomer for the treatment of diabetes mellitus | journal = Expert Opinion on Investigational Drugs | volume = 19 | issue = 2 | pages = 185–94 | date = February 2010 | pmid = 20047506 | doi = 10.1517/13543780903381411 | s2cid = 26531459 }}</ref>

<!-- Clinical data -->
| pronounce =
{{IPAc-en|ˌ|k|iː|t|oʊ|ˈ|k|oʊ|n|ə|ˌ|z|oʊ|l|,_|-|z|ɒ|l}}{{refn|{{MerriamWebsterDictionary|Ketoconazole}}
}}{{refn|{{Dictionary.com|Ketoconazole}}
}}
| tradename = Nizoral, others
| Drugs.com = {{drugs.com|monograph|ketoconazole}}
| MedlinePlus = a682816
| DailyMedID = Ketoconazole
| pregnancy_AU = B3
| pregnancy_AU_comment =
| pregnancy_category=
| routes_of_administration = [[경구 투여]] ([[알약]]), [[국소 투여]] ([[크림 (약)|크림]], [[샴푸]], 액제)
| class =
| ATC_prefix = J02
| ATC_suffix = AB02
| ATC_supplemental = {{ATC|D01|AC08}}, {{ATC|G01|AF11}}, {{ATC|H02|CA03}} <!-- Oral formulations only indicated in treatment of Cushing’s -->

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment =<ref>{{웹 인용| title=Ketoconazole HRA 200mg Tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=18 September 2017 | url=https://www.medicines.org.uk/emc/product/1767/smpc | access-date=1 April 2020 | archive-date=2 August 2020 | archive-url=https://web.archive.org/web/20200802215412/https://www.medicines.org.uk/emc/product/1767/smpc | url-status=live }}</ref><ref>{{웹 인용| title=Ketoconazole 2% w/w Shampoo - Summary of Product Characteristics (SmPC) | website=(emc) | date=5 October 2015 | url=https://www.medicines.org.uk/emc/product/4559/smpc | access-date=1 April 2020 | archive-date=3 August 2020 | archive-url=https://web.archive.org/web/20200803021950/https://www.medicines.org.uk/emc/product/4559/smpc | url-status=live }}</ref>
| legal_US = Rx-only
| legal_US_comment =<ref name="Ketoconazole tablet label">{{웹 인용| title=Ketoconazole tablet | website=DailyMed | date=26 June 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6d4be760-c723-4f54-a854-12c61cf91703 | access-date=5 January 2020 | archive-date=5 August 2020 | archive-url=https://web.archive.org/web/20200805193136/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6d4be760-c723-4f54-a854-12c61cf91703 | url-status=live }}</ref>
| legal_EU = Rx-only
| legal_EU_comment =<ref name="Ketoconazole HRA EPAR">{{웹 인용| title=Ketoconazole HRA EPAR | publisher=[[European Medicines Agency]] (EMA) | date=23 April 2012 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/ketoconazole-hra | access-date=1 April 2020 | archive-date=3 August 2020 | archive-url=https://web.archive.org/web/20200803001830/https://www.ema.europa.eu/en/medicines/human/EPAR/ketoconazole-hra | url-status=live }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_status = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = [[경구 투여|경구]]: 37~97%<ref name="Millikan2016">{{서적 인용| vauthors = Millikan LE |title=Drug Therapy in Dermatology|url=https://books.google.com/books?id=3TDMBQAAQBAJ&pg=PA82|date=19 April 2016|publisher=CRC Press|isbn=978-0-203-90831-0|pages=82–}}</ref>
| protein_bound = 84~99%
| metabolism = [[간]]에서 대부분 대사 (주로 산화, ''O''-탈알킬)
| metabolites = ''N''-deacetyl ketoconazole
| onset =
| elimination_half-life = 2단계
| duration_of_action =
| excretion = 주로 [[담도]], 그 외 [[콩팥]]<ref name="AR">{{웹 인용|title=Assessment report: Ketoconazole HRA|url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003906/WC500181493.pdf |publisher=[[European Medicines Agency]] (EMA) |access-date=26 August 2016|url-status=live|archive-url=https://web.archive.org/web/20160827011824/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003906/WC500181493.pdf|archive-date=27 August 2016}}</ref>

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 65277-42-1
| CAS_supplemental =
| PubChem = 3823
| PubChem2 = 47576
| IUPHAR_ligand = 2568
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01026
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 401695
| ChemSpiderID2 = 3691
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R9400W927I
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00351
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 48336
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 75
| ChEMBL2 = 157101
| NIAID_ChemDB =
| PDB_ligand = KTN
| synonyms = R-41400; KW-1414

<!-- Chemical and physical data -->
| IUPAC_name = 1-[4-[4-<nowiki>[[</nowiki>2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
| C=26 | H=28 | Cl=2 | N=4 | O=4
| SMILES = O=C(N5CCN(c4ccc(OC[C@@H]1O[C@](OC1)(c2ccc(Cl)cc2Cl)Cn3ccnc3)cc4)CC5)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XMAYWYJOQHXEEK-OZXSUGGESA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}}

[[파일:Ketoconazole STADA®.jpg|섬네일|150px|Stada]]
<!-- Definition and medical uses -->
'''케토코나졸'''(ketoconazole)은 '''니조랄'''(Nizoral) 등의 상품명으로 판매되는 약물로, 여러 [[진균 감염]]의 치료에 사용되는 [[항안드로겐]], [[항진균제|항진균]], [[항글루코코르티코이드]] 약제이다.<ref name="AHFS2019">{{웹 인용|title=Ketoconazole Monograph for Professionals |url=https://www.drugs.com/monograph/ketoconazole.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=23 March 2019 |archive-date=28 December 2010 |archive-url=https://web.archive.org/web/20101228050612/https://www.drugs.com/monograph/ketoconazole.html |url-status=live }}</ref> 피부에 도포하는 제형은 [[백선]], 피부 [[칸디다증]], [[어루러기]], [[비듬]], [[지루성 피부염]] 등 각종 진균의 피부 감염 치료에 사용한다.<ref name="BNF76">{{서적 인용|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=1198|edition=76}}</ref> [[경구 투여|경구]]용 약제는 덜 선호되는 치료 선택지로, 다른 약제를 쓸 수 없을 정도로 심한 감염에만 사용을 권고한다.<ref name="AHFS2019" /> 그 외에는 여성에서 남성처럼 많이 털이 자라는 [[다모증]]이나, [[쿠싱 증후군]] 치료에 쓰이기도 한다.<ref name=AHFS2019/>

<!-- Side effects and mechanisms -->
흔한 [[부작용]]으로 피부 도포 시에는 발적이 생기기도 한다.<ref name=BNF76/> 경구 약제의 비교적 흔한 부작용에는 [[구역질]], [[두통]], 간 문제 등이 있다.<ref name=AHFS2019/> [[간]] 이상은 사망에 이르거나 [[간 이식]]이 필요할 정도로 심하게 나타나기도 한다<ref name=AHFS2019/><ref name=FDA2013/> 그 외에 경구용 약제의 드물지만 심한 부작용에는 [[QT간격 연장]], [[부신겉질부전]], [[아나필락시스]]가 있다.<ref name=AHFS2019/><ref name=FDA2013>{{뉴스 인용| title=FDA limits usage of Nizoral (ketoconazole) oral tablets due to potentially fatal liver injury and risk of drug interactions and adrenal gland problems | newspaper=FDA Drug Safety Communication | url=https://www.fda.gov/Drugs/DrugSafety/ucm362415.htm | publisher=[[U.S. Food and Drug Administration]] | date=26 July 2013 | access-date=23 November 2013 | url-status=live | archive-url=https://web.archive.org/web/20131202231140/https://www.fda.gov/Drugs/DrugSafety/ucm362415.htm | archive-date=2 December 2013 }}</ref> 화학적으로 [[이미다졸]] 계열이며, 진균의 [[세포막]]에 존재하는 [[에르고스테롤]] 생산을 방해해 진균의 성장을 느리게 한다.<ref name=AHFS2019/>

<!-- Society and culture -->
[[벨기에]]의 [[얀센제약]]에서 1977년 케토코나졸의 특허를 출원했고, 의학용 사용이 시작된 것은 1981년이다.<ref name=Fis2006>{{서적 인용| vauthors = Fischer J, Ganellin CR  |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=503 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA503 }}</ref> [[복제약]]으로 이용 가능하며, [[영국]]이나 [[대한민국]] 등 여러 나라에서 피부에 국소 도포하는 약제는 [[일반의약품]]으로 구매 가능하다.<ref name=BNF76/> 2021년 한 해 동안 미국에서 300만 건 이상 처방되어, 처방 횟수 순위 161위에 올랐다.<ref>{{웹 인용| title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{웹 인용| title = Ketoconazole - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Ketoconazole | access-date = 14 January 2024 | archive-date = 8 July 2020 | archive-url = https://web.archive.org/web/20200708064013/https://clincalc.com/DrugStats/Drugs/Ketoconazole | url-status = live }}</ref> 경구용 약제는 EU와 호주에서 2013년 시장 철수했고,,<ref>{{웹 인용|title=Oral ketoconazole (Nizoral) 200 mg tablets |url=https://www.tga.gov.au/alert/oral-ketoconazole-nizoral-200-mg-tablets |website=Therapeutic Goods Administration (TGA) |access-date=23 March 2019 |date=10 October 2013 |archive-date=2 July 2015 |archive-url=https://web.archive.org/web/20150702154853/http://www.tga.gov.au/alert/oral-ketoconazole-nizoral-200-mg-tablets |url-status=live }}</ref><ref name=GuptaLyons2015/> 이후 중국에서도 2015년 철수했다.<ref>{{웹 인용| url=http://www.sfda.gov.cn/WS01/CL0087/122883.html | title=国家食品药品监督管理总局关于停止生产销售使用酮康唑口服制剂的公告（2015年第85号） | publisher=[[China Food and Drug Administration]] | date=25 June 2015 | access-date=2 July 2015 | language=zh | url-status=live | archive-url=https://web.archive.org/web/20150702151102/http://www.sfda.gov.cn/WS01/CL0087/122883.html | archive-date=2 July 2015 }}</ref> 또한 2013년 미국과 캐나다에서도 2013년 경구 약제의 사용을 제한했다.<ref name=GuptaLyons2015>{{저널 인용| vauthors = Gupta AK, Lyons DC | title = The Rise and Fall of Oral Ketoconazole | journal = [[Journal of Cutaneous Medicine and Surgery]] | volume = 19 | issue = 4 | pages = 352–7 | year = 2015 | pmid = 25775613 | doi = 10.1177/1203475415574970 | s2cid = 206695486 }}</ref>

== 각주 ==
{{각주}}

{{전거 통제}}


[[분류:아세트아마이드]]
[[분류:다이옥솔레인]]
[[분류:비스테로이드성 항안드로겐]]
[[분류:CYP17A1 억제제]]
[[분류:CYP2D6 억제제]]
[[분류:CYP3A4 억제제]]
[[분류:7α-수산화효소 억제제]]
[[분류:11β-수산화효소 억제제]]
[[분류:21-수산화효소 억제제]]
[[분류:항당질 코르티코이드]]
[[분류:방향화 효소 억제제]]
[[분류:디설피람 유사 약물]]
[[분류:이미다졸 항진균제]]
[[분류:콜레스테롤 곁사슬 절단효소 억제제]]
[[분류:내분비계 장애물질]]
[[분류:호르몬성 항암제]]
[[분류:피페라진]]
[[분류:프레그난 X 수용체 길항제]]