52-01-7
52-01-7
Chemical Structure
Spironolactone
Synonym(s): SC9420
- CAS No.: 52-01-7
- Formula:C24H32O4S
- Molecular Weight:416.57
IUPAC Name: S-((7R,8R,9S,10R,13S,14S,17R)-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
InChIKey: LXMSZDCAJNLERA-ZHYRCANASA-N
SMILES: C[C@@]12[C@](OC3=O)(CC3)CC[C@@]1([H])[C@@]([C@@H](CC4=CC5=O)SC(C)=O)([H])[C@]([C@]4(CC5)C)([H])CC2
Biological Activity: Spironolactone is an aldosterone antagonist that acts on the aldosterone mineralocorticoid receptor (IC50=24 nM) and androgen receptor (IC50=77 nM), promotes podocyte autophagy and regulates pain. Spironolactone improves hypertension-related vascular hypertrophy and remodeling by reducing angiotensin II (Ang II)-induced inflammation, reduces aldosterone-induced vascular and soft tissue calcification through PIT1-dependent signaling, and alleviates vascular dysfunction in type II diabetic mice by reducing oxidative stress and restoring NO/GC signaling; at low concentrations, it and its metabolites can interfere with aldosterone biosynthesis in the adrenal cortex and inhibit voltage-dependent Ca2+ channels to exert antihypertensive effects[1][2][3][4][5][6][7][8][9][10].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Spironolactone | 99.81% | Spironolactone is an aldosterone antagonist that acts on the aldosterone mineralocorticoid receptor (IC50=24 nM) and androgen receptor (IC50=77 nM), promotes podocyte autophagy and regulates pain. Spironolactone improves hypertension-related vascular hypertrophy and remodeling by reducing angiotensin II (Ang II)-induced inflammation, reduces aldosterone-induced vascular and soft tissue calcification through PIT1-dependent signaling, and alleviates vascular dysfunction in type II diabetic mice by reducing oxidative stress and restoring NO/GC signaling; at low concentrations, it and its metabolites can interfere with aldosterone biosynthesis in the adrenal cortex and inhibit voltage-dependent Ca2+ channels to exert antihypertensive effects. | ||||||||||||||||||||
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Spironolactone (Standard) | 98.55% | Spironolactone (Standard) is the analytical standard of Spironolactone. This product is intended for research and analytical applications. Spironolactone (SC9420) is an orally active aldosterone mineralocorticoid receptor antagonist with an IC50 of 24 nM. Spironolactone is also a potent antagonist of androgen receptor with an IC50 of 77 nM. Spironolactone promotes autophagy in podocytes. | ||||||||||||||||||||
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Spironolactone-d3 | 99.82% | Spironolactone-d3 is the deuterium labeled Spironolactone. Spironolactone (SC9420) is an orally active aldosterone mineralocorticoid receptor antagonist with an IC50 of 24 nM. Spironolactone is also a potent antagonist of androgen receptor with an IC50 of 77 nM. Spironolactone promotes autophagy in podocytes. | ||||||||||||||||||||
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Spironolactone-d3-1 | Spironolactone-d3-1 is deuterium labeled Spironolactone. Spironolactone (SC9420) is an orally active aldosterone mineralocorticoid receptor antagonist with an IC50 of 24 nM. Spironolactone is also a potent antagonist of androgen receptor with an IC50 of 77 nM. Spironolactone promotes autophagy in podocytes. | |||||||||||||||||||||
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Spironolactone-d7 | 99.96% | Spironolactone-d7 is the deuterium labeled Spironolactone. Spironolactone (SC9420) is an orally active aldosterone mineralocorticoid receptor antagonist with an IC50 of 24 nM. Spironolactone is also a potent antagonist of androgen receptor with an IC50 of 77 nM. Spironolactone promotes autophagy in podocytes. | ||||||||||||||||||||
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Spironolactone-d6-1 | 99.26% | Spironolactone-d6-1 is the deuterium labeled Spironolactone (HY-B0561). Spironolactone is an aldosterone antagonist that acts on the aldosterone mineralocorticoid receptor (IC50=24 nM) and androgen receptor (IC50=77 nM), promotes podocyte autophagy and regulates pain. Spironolactone improves hypertension-related vascular hypertrophy and remodeling by reducing angiotensin II (Ang II)-induced inflammation, reduces aldosterone-induced vascular and soft tissue calcification through PIT1-dependent signaling, and alleviates vascular dysfunction in type II diabetic mice by reducing oxidative stress and restoring NO/GC signaling; at low concentrations, it and its metabolites can interfere with aldosterone biosynthesis in the adrenal cortex and inhibit voltage-dependent Ca2+ channels to exert antihypertensive effects. | ||||||||||||||||||||
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Prorenone | Prorenone (SC 23133) is a spironolactone-type steroidal mineralocorticoid receptor (MR) antagonist that can cross the blood-brain barrier, with low affinity for glucocorticoid receptors and rat prostate androgen receptors. Prorenone inhibits the binding and action of Aldosterone (HY-113313), blocks its induced nuclear receptor activity and stimulated sodium transport, antagonizes aldosterone-induced urinary potassium excretion, and prevents aldosterone-induced elevation of blood pressure. Prorenone can be used in research related to hypertension. | |||||||||||||||||||||
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RU 26752 | RU 26752 is a steroid hormone receptor antagonist. RU 26752 can prevent hypertension caused by aldosterone (HY-113313) in rats. | |||||||||||||||||||||
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7α-Thiospironolactone | 99.85% | 7α-Thiospironolactone is the transformation product of spironolactone (HY-B0561), which can be obtained by the metabolism of Thermomyces lanuginosus. | ||||||||||||||||||||
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RU 752 | RU 752 is a potent mineralocorticoid receptors (type I or MR) antagonist. | |||||||||||||||||||||
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Spiroxasone | Spiroxasone is an orallyactive thioacetyl-containing steroid. Spiroxasone can prevent fatal renal damage and nephrocalcinosis associated with acute mercuric chloride intoxication. Spiroxasone can be used for the research of acute HgCl2 poisoning. | |||||||||||||||||||||
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6β-Hydroxy-7α-thiomethylspirolactone | 6β-Hydroxy-7α-thiomethylspirolactone is a metabolite of Spironolactone (HY-B0561). 6β-Hydroxy-7α-thiomethylspirolactone can be used in studies of cirrhotic ascites. | |||||||||||||||||||||
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Canrenone (Standard) | 98.53% | Canrenone (Standard) is the analytical standard of Canrenone. This product is intended for research and analytical applications. Canrenone (Aldadiene) is an aldosterone antagonist extensively used as a diuretic agent. | ||||||||||||||||||||
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Dicirenone | Dicirenone (SC26304) inhibits the effects of Aldosterone on urinary K+:Na+ ratios and the binding of [3H]Aldosterone to renal cytoplasmic and nuclear receptors. | |||||||||||||||||||||
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(2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate (Standard) | ≥98% | (2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate (Standard) is the analytical standard of (2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate. This product is intended for research and analytical applications. | ||||||||||||||||||||
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7α-(Thiomethyl)spironolactone | 99.80% | 7α-(Thiomethyl)spironolactone is a nuclear steroid receptor antagonist that can be used for the research of coronaviruses. | ||||||||||||||||||||
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References
- [1]. Sachiko Sakurabayashi-Kitade , et al. Aldosterone blockade by Spironolactone improves the hypertensive vascular hypertrophy and remodeling in angiotensin II overproducing transgenic mice. Atherosclerosis. 2009 Sep;206(1):54-60. [Content Brief]
- [2]. Jakob Voelkl , et al. Spironolactone ameliorates PIT1-dependent vascular osteoinduction in klotho-hypomorphic mice. J Clin Invest. 2013 Feb;123(2):812-22. [Content Brief]
- [3]. Omar M E Abdel-Salam, et al. Effect of spironolactone on pain responses in mice. EXCLI J. 2010 Feb 25:9:46-57. [Content Brief]
- [4]. Marcondes A B Silva, et al. Spironolactone treatment attenuates vascular dysfunction in type 2 diabetic mice by decreasing oxidative stress and restoring NO/GC signaling. Front Physiol. 2015 Oct 5:6:269. [Content Brief]
- [5]. Ryuzea Miura, et al. Anti-inflammatory effect of spironolactone on human peripheral blood mononuclear cells. J Pharmacol Sci. 2006 Jul;101(3):256-9. [Content Brief]
- [6]. S C Cheng, et al. Effects of Spironolactone, Canrenone and Canrenoate-K on Cytochrome P450, and 11β- and 18-Hydroxylation in Bovine and Human Adrenal Cortical Mitochondria1. Endocrinology. 1976 Oct;99(4):1097-106. [Content Brief]
- [7]. R Sorrentino. Effect of Spironolactone and Its Metabolites on Contractile Property of Isolated Rat Aorta Rings. J Cardiovasc Pharmacol. 2000 Aug;36(2):230-5. [Content Brief]
- [8]. Kim GK, et al. Oral Spironolactone in Post-teenage Female Patients with Acne Vulgaris: Practical Considerations for the Clinician Based on Current Data and Clinical Experience. J Clin Aesthet Dermatol. 2012;5(3):37-50. [Content Brief]
- [9]. Fagart J, et al. A new mode of mineralocorticoid receptor antagonism by a potent and selective nonsteroidal molecule. J Biol Chem. 2010;285(39):29932-29940. [Content Brief]
- [10]. Dong D, et al. Spironolactone alleviates diabetic nephropathy through promoting autophagy in podocytes. Int Urol Nephrol. 2019;51(4):755-764. [Content Brief]
