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<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability = 60–90%<ref name="Sica2005"/><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>
| 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"/><br />Canrenone: 99.2% (to albumin)<ref name="TakamuraMaruyama1997" />
| 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>
| 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–|deadurl=no|archiveurl=https://web.archive.org/web/20170327090209/https://books.google.com/books?id=KDDCiTQyGLsC&pg=PA403|archivedate=27 March 2017|df=}}</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–|deadurl=no|archiveurl=https://web.archive.org/web/20170327090209/https://books.google.com/books?id=KDDCiTQyGLsC&pg=PA403|archivedate=27 March 2017|df=}}</ref>

2019년 3월 16일 (토) 12:33 판

스피로놀락톤
Skeletal formula of spironolactone
Ball-and-stick model of the spironolactone molecule
체계적 명칭 (IUPAC 명명법)
S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
식별 정보
CAS 등록번호 52-01-7
ATC 코드 C03DA01
PubChem 5833
드러그뱅크 DB00421
ChemSpider 5628
화학적 성질
화학식 C24H32O4S 
분자량 416.574 g/mol
유의어 SC-9420; NSC-150339; 7α-Acetylthiospirolactone; 7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone
물리적 성질
녹는점 134–135 °C (273–275 °F)
약동학 정보
생체적합성 60–90%[1][2][3]
단백질 결합 Spironolactone: 88% (to albumin and AGP)[4]
Canrenone: 99.2% (to albumin)[4]
동등생물의약품 ?
약물 대사 Liver, others:
• Deacetylation via CES
• S-Oxygenation via FOM
• S-Methylation via TMT
• Dethioacetylation
• Hydroxylation via CYP3A4
• Lactone hydrolysis via PON3)[1][2][5][6][7][8][9]
생물학적 반감기 Spironolactone: 1.4 hrs[1]
7α-TMS: 13.8 hours[1]
6β-OH-7α-TMS: 15.0 hrs[1]
Canrenone: 16.5 hours[1]
배출 Urine, bile[2]
처방 주의사항
임부투여안전성 B3(오스트레일리아)C(미국)
법적 상태
투여 방법 By mouth,[10] topical[11]

스피로놀락톤(Spironolactone)은 항알도스테론제, 칼륨 보존성 이뇨제 중의 하나로, 체내 알도스테론과 그의 수용체끼리의 결합을 억제하여 체내 칼륨 이온을 보존하는 이뇨 작용을 나타낸다. 주로 심부전, 간경변성 복수, 고혈압 치료제에 사용되며, 저칼률혈증에 대한 보조적인 치료약으로도 활용된다. 남성 호르몬을 억제하는 부작용으로 인해 여성형 유방, 유방통, 피부 발진 등을 일으키나 이것을 응용해 여성에게 발병되는 남성형 탈모증과 여드름 치료제로 이용하기도 한다.

각주

  1. ↑ 가 나 다 라 마 바 Sica, Domenic A. (2005). “Pharmacokinetics and Pharmacodynamics of Mineralocorticoid Blocking Agents and their Effects on Potassium Homeostasis”. 《Heart Failure Reviews》 10 (1): 23–29. doi:10.1007/s10741-005-2345-1. ISSN 1382-4147. PMID 15947888. 
  2. ↑ 가 나 다 Maron BA, Leopold JA (2008). “Mineralocorticoid receptor antagonists and endothelial function”. 《Curr Opin Investig Drugs》 9 (9): 963–9. PMC 2967484. PMID 18729003. 
  3. ↑ Carone, Laura; Oxberry, Stephen G.; Twycross, Robert; Charlesworth, Sarah; Mihalyo, Mary; Wilcock, Andrew (2017). “Spironolactone”. 《Journal of Pain and Symptom Management》 53 (2): 288–292. doi:10.1016/j.jpainsymman.2016.12.320. ISSN 0885-3924. PMID 28024992. 
  4. ↑ 가 나 Takamura, Norito; Maruyama, Toru; Ahmed, Shamim; Suenaga, Ayaka; Otagiri, Masaki (1997). “Interactions of Aldosterone Antagonist Diuretics with Human Serum Proteins”. 《Pharmaceutical Research》 14 (4): 522–526. doi:10.1023/A:1012168020545. ISSN 0724-8741. 
  5. ↑ Andrew Parkinson (2001). 《Biotransformation of Xenobiotics》. McGraw-Hill. 137–138,169,171,180,195,208쪽. 
  6. ↑ Curtis D. Klaassen (2007년 12월 11일). 《Casarett & Doull's Toxicology: The Basic Science of Poisons, Seventh Edition》. McGraw Hill Professional. 173쪽. ISBN 978-0-07-159351-9. 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). 
  7. ↑ Los LE, Pitzenberger SM, Ramjit HG, Coddington AB, Colby HD (1994). “Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites”. 《Drug Metab. Dispos.》 22 (6): 903–8. PMID 7895608. 
  8. ↑ Henry R. Black; William Elliott (2006년 12월 28일). 《Hypertension: A Companion to Braunwald's Heart Disease》. Elsevier Health Sciences. 295–쪽. ISBN 978-1-4377-1078-6. 
  9. ↑ Draganov DI, La Du BN (January 2004). “Pharmacogenetics of paraoxonases: a brief review”. 《Naunyn Schmiedebergs Arch. Pharmacol.》 369 (1): 78–88. doi:10.1007/s00210-003-0833-1. PMID 14579013. 
  10. ↑ “Spironolactone”. The American Society of Health-System Pharmacists. 2015년 11월 16일에 보존된 문서. Oct 24, 2015에 확인함. 
  11. ↑ NADIR R. FARID; Evanthia Diamanti-Kandarakis (2009년 2월 27일). 《Diagnosis and Management of Polycystic Ovary Syndrome》. Springer Science & Business Media. 235–쪽. ISBN 978-0-387-09718-3. 
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