{{위키데이터 속성 추적}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 470470172
| IUPAC_name = ''S''-[(7''R'',8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-10,13-Dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1''H''-cyclopenta[''a'']phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
| image = Spironolactone Structural Formula V1.svg
| alt = Skeletal formula of spironolactone
| width = 235px
| image2 = Spironolactone 3D ball.png
| alt2 = Ball-and-stick model of the spironolactone molecule
| width2 = 225px

<!--Clinical data-->
| pronounce = {{IPAc-en|ˌ|s|p|aɪ|r|oʊ|n|oʊ|ˈ|l|æ|k|t|oʊ|n}} {{respell|SPY|roh|noh|LAK|tone}},<ref name="LoughlinGenerali2006">{{서적 인용|author1=Kevin R. Loughlin|author2=Joyce A. Generali|title=The Guide to Off-label Prescription Drugs: New Uses for FDA-approved Prescription Drugs|url=https://books.google.com/books?id=fhEFkBxEtH8C&pg=PA131|year=2006|publisher=Simon and Schuster|isbn=978-0-7432-8667-1|pages=131–}}</ref> {{IPAc-en|ˌ|s|p|ɪər|oʊ|n|oʊ|ˈ|l|æ|k|t|oʊ|n}} {{respell|SPEER|oh|noh|LAK|tone}}<ref name="ClarkHarvey2011">{{서적 인용|author1=Michelle A. Clark|author2=Richard A. Harvey|author3=Richard Finkel |author4=Jose A. Rey |author5=Karen Whalen |title=Pharmacology|url=https://books.google.com/books?id=Y558dgp_PjoC&pg=PA337|date=15 December 2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-1314-3|pages=286, 337}}</ref>
| tradename = Aldactone, Spiractin, Verospiron, [[#Brand names|many others]]; combinations: Aldactazide (+{{abbrlink|HCTZ|hydrochlorothiazide}}), Aldactide (+{{abbrlink|HFMZ|hydroflumethiazide}}), Aldactazine (+[[altizide]]), [[#Brand names|others]]
| Drugs.com = {{drugs.com|monograph|spironolactone}}
| MedlinePlus = a682627
| pregnancy_AU = B3
| pregnancy_US = C
| legal_UK = POM
| legal_US = Rx-only
| routes_of_administration = [[Oral administration|By mouth]],<ref name="AHFS2015">{{웹 인용|title=Spironolactone|url=https://www.drugs.com/monograph/spironolactone.html|publisher=The American Society of Health-System Pharmacists|accessdate=Oct 24, 2015|url-status=live|archiveurl=https://web.archive.org/web/20151116054857/http://www.drugs.com/monograph/spironolactone.html|archivedate=2015-11-16|df=}}</ref> [[topical]]<ref name="FARIDDiamanti-Kandarakis2009">{{서적 인용|author1=NADIR R. FARID|author2=Evanthia Diamanti-Kandarakis|title=Diagnosis and Management of Polycystic Ovary Syndrome|url=https://books.google.com/books?id=fgMYVxmPDnMC&pg=PA235|date=27 February 2009|publisher=Springer Science & Business Media|isbn=978-0-387-09718-3|pages=235–}}</ref>
| class = [[Antimineralocorticoid]]; [[Steroidal antiandrogen]]

<!--Pharmacokinetic data-->
| bioavailability = 60–90%<ref name="Sica2005">{{저널 인용|last1=Sica|first1=Domenic A.|title=Pharmacokinetics and Pharmacodynamics of Mineralocorticoid Blocking Agents and their Effects on Potassium Homeostasis|journal=Heart Failure Reviews|volume=10|issue=1|year=2005|pages=23–29|issn=1382-4147|doi=10.1007/s10741-005-2345-1|pmid=15947888}}</ref><ref name="pmid18729003">{{저널 인용| vauthors = Maron BA, Leopold JA | title = Mineralocorticoid receptor antagonists and endothelial function | journal = Curr Opin Investig Drugs | volume = 9 | issue = 9 | pages = 963–9 | year = 2008 | pmid = 18729003 | pmc = 2967484 | doi = | url = }}</ref><ref name="CaroneOxberry2017">{{저널 인용|last1=Carone|first1=Laura|last2=Oxberry|first2=Stephen G.|last3=Twycross|first3=Robert|last4=Charlesworth|first4=Sarah|last5=Mihalyo|first5=Mary|last6=Wilcock|first6=Andrew|title=Spironolactone|journal=Journal of Pain and Symptom Management|volume=53|issue=2|year=2017|pages=288–292|issn=0885-3924|doi=10.1016/j.jpainsymman.2016.12.320|pmid=28024992}}</ref>
| protein_bound = Spironolactone: 88% (to [[human serum albumin|albumin]] and {{abbrlink|AGP|alpha-1-acid glycoprotein}})<ref name="TakamuraMaruyama1997">{{저널 인용|last1=Takamura|first1=Norito|last2=Maruyama|first2=Toru|last3=Ahmed|first3=Shamim|last4=Suenaga|first4=Ayaka|last5=Otagiri|first5=Masaki |title=Interactions of Aldosterone Antagonist Diuretics with Human Serum Proteins |journal=Pharmaceutical Research|volume=14|issue=4|year=1997|pages=522–526|issn=0724-8741 |doi=10.1023/A:1012168020545}}</ref><br />Canrenone: 99.2% (to albumin)<ref name="TakamuraMaruyama1997" />
| metabolism = [[Liver]], others:<br />• [[Deacetylation]] via {{abbrlink|CES|carboxylesterase}}<br />• ''S''-[[Oxidation|Oxygenation]] via {{abbrlink|FOM|flavin-containing monooxygenase}}<br />• ''S''-[[Methylation]] via {{abbrlink|TMT|thiol S-methyltransferase}}<br />• [[Dethioacetylation]]<br />• [[Hydroxylation]] via [[CYP3A4]]<br />• [[Lactone]] [[hydrolysis]] via [[PON3]])<ref name="Sica2005" /><ref name="pmid18729003" /><ref name="Parkinson2001">{{서적 인용|author=Andrew Parkinson|title=Biotransformation of Xenobiotics|url=https://books.google.com/books?id=pAovcgAACAAJ|year=2001|publisher=McGraw-Hill|pages=137–138,169,171,180,195,208}}</ref><ref name="Klaassen2007">{{서적 인용|author=Curtis D. Klaassen|title=Casarett & Doull's Toxicology: The Basic Science of Poisons, Seventh Edition|url=https://books.google.com/books?id=4yi7-j48uhIC|date=11 December 2007|publisher=McGraw Hill Professional|isbn=978-0-07-159351-9|page=173|quote=Some P450 enzymes (such as the rate enzyme CYP2A1) preferentially catalyze the 6α-hydroxylation reaction, whereas other P450 enzymes (such as the CYP3A enzymes in all mammalian species) preferentially catalyze the 6β-hydroxylation reaction (which is a major route of hepatic steroid biotransformation).}}</ref><ref name="pmid7895608">{{저널 인용| vauthors = Los LE, Pitzenberger SM, Ramjit HG, Coddington AB, Colby HD | title = Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites | journal = Drug Metab. Dispos. | volume = 22 | issue = 6 | pages = 903–8 | date = 1994 | pmid = 7895608 | doi = | url = http://dmd.aspetjournals.org/content/22/6/903}}</ref><ref name="BlackElliott2006">{{서적 인용|author1=Henry R. Black|author2=William Elliott|title=Hypertension: A Companion to Braunwald's Heart Disease|url=https://books.google.com/books?id=42Fcmne6_w8C&pg=PA295|date=28 December 2006|publisher=Elsevier Health Sciences|isbn=978-1-4377-1078-6|pages=295–}}</ref><ref name="pmid14579013">{{저널 인용| vauthors = Draganov DI, La Du BN | title = Pharmacogenetics of paraoxonases: a brief review | journal = Naunyn Schmiedebergs Arch. Pharmacol. | volume = 369 | issue = 1 | pages = 78–88 | date = January 2004 | pmid = 14579013 | doi = 10.1007/s00210-003-0833-1 | url = }}</ref>
| metabolites = {{abbrlink|7α-TS|7α-Thiospironolactone}}, {{abbrlink|7α-TMS|7α-thiomethylspironolactone}}, {{abbrlink|6β-OH-7α-TMS|6β-hydroxy-7α-thiomethylspironolactone}}, [[canrenone]], others<ref name="Sica2005" /><ref name="pmid18729003" /><ref name="SzaszBudvari-Barany1990" /><br />(All three active)<ref name="McDonaghGardner2011">{{서적 인용|author1=Theresa A. McDonagh|author2=Roy S. Gardner|author3=Andrew L. Clark|author4=Henry Dargie|title=Oxford Textbook of Heart Failure|url=https://books.google.com/books?id=KDDCiTQyGLsC&pg=PA403|date=14 July 2011|publisher=OUP Oxford|isbn=978-0-19-957772-9|pages=403–|url-status=live|archiveurl=https://web.archive.org/web/20170327090209/https://books.google.com/books?id=KDDCiTQyGLsC&pg=PA403|archivedate=27 March 2017|df=}}</ref>
| elimination_half-life = Spironolactone: 1.4 hrs<ref name="Sica2005" /><br />{{abbrlink|7α-TMS|7α-thiomethylspironolactone}}: 13.8 hours<ref name="Sica2005" /><br />{{abbrlink|6β-OH-7α-TMS|6β-hydroxy-7α-thiomethylspironolactone}}: 15.0 hrs<ref name="Sica2005" /><br />[[Canrenone]]: 16.5 hours<ref name="Sica2005" />
| excretion = [[Urine]], [[bile]]<ref name="pmid18729003" />

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 52-01-7
| ATC_prefix = C03
| ATC_suffix = DA01
| ATC_supplemental = 
| PubChem = 5833
| IUPHAR_ligand = 2875
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00421
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5628
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 27O7W4T232
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00443
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9241
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1393
| synonyms = SC-9420; NSC-150339; 7α-Acetylthiospirolactone; 7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone

<!--Chemical data-->
| C=24 | H=32 | O=4 | S=1
| molecular_weight = 416.574 g/mol
| SMILES = O=C5O[C@@]4([C@@]3([C@H]([C@@H]2[C@H](SC(=O)C)C/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)CC4)C)CC5
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LXMSZDCAJNLERA-ZHYRCANASA-N

<!--Physical data-->
| melting_point = 134
| melting_high = 135
}}
'''스피로놀락톤'''({{llang|en|spironolactone}})은 항알도스테론제, 칼륨 보존성 [[이뇨제]], [[스피로 화합물]] 중의 하나로, 체내 [[알도스테론]]과 그의 수용체끼리의 결합을 억제하여 체내 칼륨 이온을 보존하는 이뇨 작용을 나타낸다. 주로 심부전, 간경변성 복수, 고혈압 치료제에 사용되며, [[저칼륨혈증]]에 대한 보조적인 치료약으로도 활용된다. [[남성 호르몬]]을 억제하는 부작용으로 인해 [[여성형 유방]], 유방통, [[피부]] 발진 등을 일으키나 이것을 응용해 [[여성]]에게 발병되는 [[남성형 탈모증]]과 [[여드름]] 치료제로 이용하기도 한다. 또한 트랜스젠더의 [[트랜스젠더 호르몬 치료 (MTF)|여성화 호르몬 치료]]에도 이용된다.

== 같이 보기 ==
* [[락톤]]

== 각주 ==
{{각주}}

{{이뇨제}}

{{전거 통제}}

[[분류:전구약물]]
[[분류:프로게스토겐]]
[[분류:아세트산 에스터]]
[[분류:락톤]]
[[분류:항안드로겐]]
[[분류:싸이오에스터]]
[[분류:5α-환원 효소 억제제]]
[[분류:스피로 화합물]]
[[분류:프레그난]]
[[분류:세계 반도핑 기구 금지 약물]]
[[분류:세계 보건 기구 필수 의약품]]
[[분류:프레그난 X 수용체 작용제]]
[[분류:스테로이드성 항안드로겐]]
[[분류:CYP17A1 억제제]]
[[분류:콜레스테롤 곁사슬 절단효소 억제제]]
[[분류:3β-하이드록시스테로이드 탈수소효소 억제제]]
[[분류:11β-수산화효소 억제제]]
[[분류:17β-하이드록시스테로이드 탈수소효소 억제제]]
[[분류:21-수산화효소 억제제]]
[[분류:선택적 에스트로겐 수용체 조절제]]
[[분류:여드름 치료제]]