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MedKoo Cat#: 318754 | Name: Spironolactone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Spironolactone is a medication primarily used to treat fluid build-up due to heart failure, liver scarring, or kidney disease. Other uses include high blood pressure, low blood potassium that does not improve with supplementation, early puberty, excessive hair growth in women, hormonal/cystic acne and as a component of hormone replacement therapy for trans women.

Chemical Structure

Spironolactone
Spironolactone
CAS#52-01-7

Theoretical Analysis

MedKoo Cat#: 318754

Name: Spironolactone

CAS#: 52-01-7

Chemical Formula: C24H32O4S

Exact Mass: 416.2021

Molecular Weight: 416.58

Elemental Analysis: C, 69.20; H, 7.74; O, 15.36; S, 7.70

Price and Availability

Size Price Availability Quantity
1g USD 150.00 2 weeks
5g USD 300.00 2 weeks
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Related CAS #
No Data
Synonym
SC9420; SC-9420; SC 9420; Spironolactone; Spiresis; Spiridon
IUPAC/Chemical Name
S-((7R,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl) ethanethioate
InChi Key
LXMSZDCAJNLERA-NMFLDQOASA-N
InChi Code
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
SMILES Code
O=C(O1)CC[C@]12CC[C@@]3([H])[C@]4([H])[C@H](SC(C)=O)CC5=CC(CC[C@]5(C)[C@@]4([H])CC[C@]23C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Spironolactone is a potent antagonist of the androgen receptor with an IC50 of 77 nM.
In vitro activity:
Spironolactone has potential to counter methylglyoxal (MG)-induced cytotoxicity. In MC3T3-E1 osteoblastic cells, spironolactone prevented MG-induced cell death and improved bone formation activity. It reduced oxidative damage, inflammatory cytokines, and endoplasmic reticulum stress, while increasing glutathione levels and glyoxalase I activity. Spironolactone also mitigated mitochondrial dysfunction induced by MG, restoring markers of mitochondrial biogenesis. Reference: J Korean Med Sci. 2021 Oct 4;36(38):e265. https://pubmed.ncbi.nlm.nih.gov/34609092/
In vivo activity:
Spironolactone has potential therapeutic benefit in the treatment of chronic kidney disease (CKD)-associated vascular calcification. In patients on hemodialysis from the MiREnDa trial, spironolactone treatment improved serum calcification propensity. In mouse models and human aortic smooth muscle cells (HAoSMCs), spironolactone treatment ameliorated vascular calcification and expression of osteogenic markers. Reference: Biochem Biophys Res Commun. 2021 Dec 10;582:28-34. https://pubmed.ncbi.nlm.nih.gov/34678593/
Solvent mg/mL mM comments
Solubility
DMSO 41.7 100.00
Ethanol 20.8 50.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 416.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Park SY, Suh KS, Jung WW, Chin SO. Spironolactone Attenuates Methylglyoxal-induced Cellular Dysfunction in MC3T3-E1 Osteoblastic Cells. J Korean Med Sci. 2021 Oct 4;36(38):e265. doi: 10.3346/jkms.2021.36.e265. PMID: 34609092; PMCID: PMC8490790. 2. Chauhan AK, Li P, Sun Y, Wani G, Zhu Q, Wani AA. Spironolactone-induced XPB degradation requires TFIIH integrity and ubiquitin-selective segregase VCP/p97. Cell Cycle. 2021 Jan;20(1):81-95. doi: 10.1080/15384101.2020.1860559. Epub 2020 Dec 31. PMID: 33381997; PMCID: PMC7849777. 3. Hammer F, Buehling SS, Masyout J, Malzahn U, Hauser T, Auer T, Grebe S, Feger M, Tuffaha R, Degenhart G, Lang F, Pasch A, Alesutan I, Wanner C, Krane V, Voelkl J. Protective effects of spironolactone on vascular calcification in chronic kidney disease. Biochem Biophys Res Commun. 2021 Dec 10;582:28-34. doi: 10.1016/j.bbrc.2021.10.023. Epub 2021 Oct 10. PMID: 34678593. 4. Stephan M, Schoeller J, Raabe FJ, Schmitt A, Hasan A, Falkai P, Jensen N, Rossner MJ. Spironolactone alleviates schizophrenia-related reversal learning in Tcf4 transgenic mice subjected to social defeat. Schizophrenia (Heidelb). 2022 Sep 29;8(1):77. doi: 10.1038/s41537-022-00290-4. PMID: 36171421; PMCID: PMC9519974.
In vitro protocol:
1. Park SY, Suh KS, Jung WW, Chin SO. Spironolactone Attenuates Methylglyoxal-induced Cellular Dysfunction in MC3T3-E1 Osteoblastic Cells. J Korean Med Sci. 2021 Oct 4;36(38):e265. doi: 10.3346/jkms.2021.36.e265. PMID: 34609092; PMCID: PMC8490790. 2. Chauhan AK, Li P, Sun Y, Wani G, Zhu Q, Wani AA. Spironolactone-induced XPB degradation requires TFIIH integrity and ubiquitin-selective segregase VCP/p97. Cell Cycle. 2021 Jan;20(1):81-95. doi: 10.1080/15384101.2020.1860559. Epub 2020 Dec 31. PMID: 33381997; PMCID: PMC7849777.
In vivo protocol:
1. Hammer F, Buehling SS, Masyout J, Malzahn U, Hauser T, Auer T, Grebe S, Feger M, Tuffaha R, Degenhart G, Lang F, Pasch A, Alesutan I, Wanner C, Krane V, Voelkl J. Protective effects of spironolactone on vascular calcification in chronic kidney disease. Biochem Biophys Res Commun. 2021 Dec 10;582:28-34. doi: 10.1016/j.bbrc.2021.10.023. Epub 2021 Oct 10. PMID: 34678593. 2. Stephan M, Schoeller J, Raabe FJ, Schmitt A, Hasan A, Falkai P, Jensen N, Rossner MJ. Spironolactone alleviates schizophrenia-related reversal learning in Tcf4 transgenic mice subjected to social defeat. Schizophrenia (Heidelb). 2022 Sep 29;8(1):77. doi: 10.1038/s41537-022-00290-4. PMID: 36171421; PMCID: PMC9519974.
1: Lainscak M, Pelliccia F, Rosano G, Vitale C, Schiariti M, Greco C, Speziale G, Gaudio C. Safety profile of mineralocorticoid receptor antagonists: Spironolactone and eplerenone. Int J Cardiol. 2015 Dec 1;200:25-9. doi: 10.1016/j.ijcard.2015.05.127. Epub 2015 May 21. Review. PubMed PMID: 26404748. 2: Seferovic PM, Pelliccia F, Zivkovic I, Ristic A, Lalic N, Seferovic J, Simeunovic D, Milinkovic I, Rosano G. Mineralocorticoid receptor antagonists, a class beyond spironolactone--Focus on the special pharmacologic properties of eplerenone. Int J Cardiol. 2015 Dec 1;200:3-7. doi: 10.1016/j.ijcard.2015.02.096. Review. PubMed PMID: 26404746. 3: Hou J, Xiong W, Cao L, Wen X, Li A. Spironolactone Add-on for Preventing or Slowing the Progression of Diabetic Nephropathy: A Meta-analysis. Clin Ther. 2015 Sep;37(9):2086-2103.e10. doi: 10.1016/j.clinthera.2015.05.508. Epub 2015 Aug 5. Review. PubMed PMID: 26254276. 4: Agrawal S, Agrawal N, Garg J, Mohandas R, Gupta T, Segal M. Heart failure and chronic kidney disease: should we use spironolactone? Am J Med Sci. 2015 Aug;350(2):147-51. doi: 10.1097/MAJ.0000000000000514. Review. PubMed PMID: 26086152. 5: Widimský J Sr. [Effect of spironolactone in patients with heart failure and preserved left ventricular function - TOPCAT study]. Vnitr Lek. 2015 May;61(5):376-80. Review. Czech. PubMed PMID: 26075843. 6: Danjuma MI, Mukherjee I, Makaronidis J, Osula S. Converging indications of aldosterone antagonists (spironolactone and eplerenone): a narrative review of safety profiles. Curr Hypertens Rep. 2014 Feb;16(2):414. doi: 10.1007/s11906-013-0414-8. Review. PubMed PMID: 24407447. 7: Jolobe OM. Evolving strategies for the use of spironolactone in cardiovascular disease. Eur J Intern Med. 2013 Jun;24(4):303-9. doi: 10.1016/j.ejim.2012.11.007. Epub 2012 Dec 12. Review. PubMed PMID: 23245930. 8: Colussi G, Catena C, Sechi LA. Spironolactone, eplerenone and the new aldosterone blockers in endocrine and primary hypertension. J Hypertens. 2013 Jan;31(1):3-15. doi: 10.1097/HJH.0b013e3283599b6a. Review. PubMed PMID: 23011526. 9: Segar JL. Neonatal diuretic therapy: furosemide, thiazides, and spironolactone. Clin Perinatol. 2012 Mar;39(1):209-20. doi: 10.1016/j.clp.2011.12.007. Epub 2011 Dec 29. Review. PubMed PMID: 22341547. 10: Rathnayake D, Sinclair R. Use of spironolactone in dermatology. Skinmed. 2010 Nov-Dec;8(6):328-32; quiz 333. Review. PubMed PMID: 21413648. 11: Marrs JC. Spironolactone management of resistant hypertension. Ann Pharmacother. 2010 Nov;44(11):1762-9. doi: 10.1345/aph.1P338. Epub 2010 Oct 26. Review. PubMed PMID: 20978214. 12: Chua D, Lo A, Lo C. Spironolactone use in heart failure patients with end-stage renal disease on hemodialysis: is it safe? Clin Cardiol. 2010 Oct;33(10):604-8. doi: 10.1002/clc.20838. Review. PubMed PMID: 20960534. 13: Batterink J, Stabler SN, Tejani AM, Fowkes CT. Spironolactone for hypertension. Cochrane Database Syst Rev. 2010 Aug 4;(8):CD008169. doi: 10.1002/14651858.CD008169.pub2. Review. PubMed PMID: 20687095. 14: Brown J, Farquhar C, Lee O, Toomath R, Jepson RG. Spironolactone versus placebo or in combination with steroids for hirsutism and/or acne. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD000194. doi: 10.1002/14651858.CD000194.pub2. Review. PubMed PMID: 19370553. 15: Inada M, Iwasaki K, Imai C, Hashimoto S. Spironolactone effective hypertension in the elderly due to 11beta-hydroxysteroid dehydrogenase type 2 (11beta-HSD2) impairment: contributory role of determining serum cortisol/cortisone ratio as a marker of 11beta-HSD2 activity. Intern Med. 2008;47(24):2157-64. Epub 2008 Dec 15. Review. PubMed PMID: 19075542. 16: Bomback AS, Kshirsagar AV, Klemmer PJ. Renal aspirin: will all patients with chronic kidney disease one day take spironolactone? Nat Clin Pract Nephrol. 2009 Feb;5(2):74-5. doi: 10.1038/ncpneph1004. Epub 2008 Nov 25. Review. PubMed PMID: 19029998; PubMed Central PMCID: PMC2845907. 17: Struthers A, Krum H, Williams GH. A comparison of the aldosterone-blocking agents eplerenone and spironolactone. Clin Cardiol. 2008 Apr;31(4):153-8. doi: 10.1002/clc.20324. Review. PubMed PMID: 18404673. 18: Handler J. Well tolerated spironolactone-related hyponatremia. J Clin Hypertens (Greenwich). 2008 Apr;10(4):317-21. Review. PubMed PMID: 18401230. 19: Yoshimura M. [Spironolactone as a cardio-protective drug]. Nihon Rinsho. 2007 May 28;65 Suppl 5:107-9. Review. Japanese. PubMed PMID: 17569309. 20: Sica DA. Spironolactone: an old friend rediscovered. J Clin Hypertens (Greenwich). 2006 Jul;8(7):467-9. Review. PubMed PMID: 16849899.