Spironolakton

Spironolakton
Nama sistematis (IUPAC)
	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
Data klinis
Nama dagang	Aldactone, Spiractin, Verospiron, dll; kombinasi: Aldactazide (+HCTZ), Aldactide (+HFMZ), Aldactazine (+altizide), dll
AHFS/Drugs.com	monograph
MedlinePlus	a682627
Data lisensi	US Daily Med:pranala
Kat. kehamilan	B3(AU) C(US)
Status hukum	POM (UK) ℞-only (US)
Rute	Lewat mulut, topikal
Data farmakokinetik
Bioavailabilitas	60–90%
Ikatan protein	Spironolactone: 88% (pada albumin dan AGP); Canrenone: 99.2% (pada albumin)
Metabolisme	Liver, lainnya:; • Deacetylation via CES; • S-Oxygenation via FOM; • S-Methylation via TMT; • Dethioacetylation; • Hydroxylation via CYP3A4; • Lactone hydrolysis via PON3)
Waktu paruh	Spironolactone: 1.4 jam; 7α-TMS: 13.8 jam; 6β-OH-7α-TMS: 15.0 jam; Canrenone: 16.5 jam
Ekskresi	Urin, empedu
Pengenal
Nomor CAS	52-01-7
Kode ATC	C03DA01
PubChem	CID 5833
Ligan IUPHAR	2875
DrugBank	DB00421
ChemSpider	5628
UNII	27O7W4T232
KEGG	D00443
ChEBI	CHEBI:9241
ChEMBL	CHEMBL1393
Sinonim	SC-9420; NSC-150339; 7α-Acetylthiospirolactone; 7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone
Data kimia
Rumus	C24H32O4S
Massa mol.	416.574 g/mol
	InChI InChI=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 ; Key:LXMSZDCAJNLERA-ZHYRCANASA-N ;
Data fisik
Titik lebur	134–135 °C (273–275 °F)

Spironolakton, dijual dengan merk dagang Aldactone, adalah obat yang digunakan untuk menangani sembap atau edema akibat gagal jantung, sirosis hati, atau penyakit ginjal.^[1] Obat ini juga dipakai untuk menangani hipertensi (tekanan darah tinggi), kadar kalium yang rendah dalam darah dan tak kunjung membaik walau sudah mengonsumsi suplemen, pubertas dini pada laki-laki, jerawat, dan pertumbuhan rambut yang berlebihan pada wanita. Spironolakton bahkan juga dapat dimanfaatkan untuk terapi hormon feminin untuk wanita transgender.^[1]^[12]^[13] Spironolakton dikonsumsi lewat mulut.^[1]

^ ^a ^b ^c ^d "Spironolactone". The American Society of Health-System Pharmacists. Diarsipkan dari versi asli tanggal 2015-11-16. Diakses tanggal Oct 24, 2015.
^ NADIR R. FARID; Evanthia Diamanti-Kandarakis (27 February 2009). Diagnosis and Management of Polycystic Ovary Syndrome. Springer Science & Business Media. hlm. 235–. ISBN 978-0-387-09718-3.
^ ^a ^b ^c ^d ^e ^f 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.
^ ^a ^b ^c Maron BA, Leopold JA (2008). "Mineralocorticoid receptor antagonists and endothelial function". Curr Opin Investig Drugs. 9 (9): 963–9. PMC 2967484 . PMID 18729003.
^ 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.
^ ^a ^b 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. PMID 9144743.
^ Andrew Parkinson (2001). Biotransformation of Xenobiotics. McGraw-Hill. hlm. 137–138, 169, 171, 180, 195, 208.
^ Curtis D. Klaassen (11 December 2007). Casarett & Doull's Toxicology: The Basic Science of Poisons, Seventh Edition. McGraw Hill Professional. hlm. 173. 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).
^ 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.
^ Henry R. Black; William Elliott (28 December 2006). Hypertension: A Companion to Braunwald's Heart Disease. Elsevier Health Sciences. hlm. 295–. ISBN 978-1-4377-1078-6.
^ 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. hdl:2027.42/46312. PMID 14579013.
^ Friedman, Adam J. (1 October 2015). "Spironolactone for Adult Female Acne". Cutis. 96 (4): 216–217. ISSN 2326-6929. PMID 27141564.
^ Maizes, Victoria (2015). Integrative Women's Health (edisi ke-2). hlm. 746. ISBN 9780190214807.

[AHFS2015-1] "Spironolactone". The American Society of Health-System Pharmacists. Diarsipkan dari versi asli tanggal 2015-11-16. Diakses tanggal Oct 24, 2015.

[FARIDDiamanti-Kandarakis2009-2] NADIR R. FARID; Evanthia Diamanti-Kandarakis (27 February 2009). Diagnosis and Management of Polycystic Ovary Syndrome. Springer Science & Business Media. hlm. 235–. ISBN 978-0-387-09718-3.

[Sica2005-3] ^ ^a ^b ^c ^d ^e ^f 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.

[pmid18729003-4] Maron BA, Leopold JA (2008). "Mineralocorticoid receptor antagonists and endothelial function". Curr Opin Investig Drugs. 9 (9): 963–9. PMC 2967484 . PMID 18729003.

[CaroneOxberry2017-5] 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.

[TakamuraMaruyama1997-6] 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. PMID 9144743.

[Parkinson2001-7] Andrew Parkinson (2001). Biotransformation of Xenobiotics. McGraw-Hill. hlm. 137–138, 169, 171, 180, 195, 208.

[Klaassen2007-8] Curtis D. Klaassen (11 December 2007). Casarett & Doull's Toxicology: The Basic Science of Poisons, Seventh Edition. McGraw Hill Professional. hlm. 173. 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).

[pmid7895608-9] 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.

[BlackElliott2006-10] Henry R. Black; William Elliott (28 December 2006). Hypertension: A Companion to Braunwald's Heart Disease. Elsevier Health Sciences. hlm. 295–. ISBN 978-1-4377-1078-6.

[pmid14579013-11] 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. hdl:2027.42/46312. PMID 14579013.

[12] Friedman, Adam J. (1 October 2015). "Spironolactone for Adult Female Acne". Cutis. 96 (4): 216–217. ISSN 2326-6929. PMID 27141564.

[13] Maizes, Victoria (2015). Integrative Women's Health (edisi ke-2). hlm. 746. ISBN 9780190214807.

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