S3378

Sigma-Aldrich

Spironolactone

97.0-103.0%

Synonym(s):
4-Pregnen-21-oic acid-17α-ol-3-one-7α-thiol γ-lactone 7-acetate, 7α-(Acetylthio)-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone
Empirical Formula (Hill Notation):
C24H32O4S
CAS Number:
Molecular Weight:
416.57
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

97.0-103.0%

mp

207-208 °C (lit.)

solubility

chloroform: complete 50 mg/ml, clear, faintly yellow

originator

Pfizer

SMILES string

CC(=O)S[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]45CCC(=O)O5)[C@H]13

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

InChI key

LXMSZDCAJNLERA-ZHYRCANASA-N

Gene Information

human ... HSD17B1(3292), NR3C2(4306)
rat ... Ar(24208)

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Related Categories

Application

Spironolactone was added to rat diet to study the effect of long-term spironolactone use on renal function.

Packaging

1, 5 g in glass bottle

Biochem/physiol Actions

Spironolactone reduces aldosterone-induced potassium/magnesium loss and myocardial fibrosis. It reduces hypertension, improves the endothelial function and reduces the overall morbidity and mortality in patients with chronic heart failure. Spironolactone improves nitric oxide bioactivity and vascular endothelial vasodilator dysfunction.
Spironolactone is a competitive aldosterone receptor antagonist. Used as potassium sparing diuretic.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Preparation Note

Spironolactone yields clear, faint yellow solution in chloroform at 50 mg/ml.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S3378.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Jakob Nielsen et al.
American journal of physiology. Renal physiology, 283(5), F923-F933 (2002-10-10)
Renal tubule profiling studies were carried out to investigate the long-term effects of administration of spironolactone, a mineralocorticoid receptor antagonist, on abundances of the major Na transporter and Na channel proteins along the rat renal tubule. Oral administration of spironolactone...
Femke Waanders et al.
American journal of physiology. Renal physiology, 296(5), F1072-F1079 (2009-02-27)
Chronic transplant dysfunction (CTD) is the leading cause of long-term renal allograft loss and is characterized by specific histological lesions including transplant vasculopathy, interstitial fibrosis, and focal glomerulosclerosis. Increasing evidence indicates that aldosterone is a direct mediator of renal damage...
Donna A Volpe et al.
The AAPS journal, 16(1), 172-180 (2013-12-18)
Drug interactions due to efflux transporters may result in one drug increasing or decreasing the systemic exposure of a second drug. The potential for in vivo drug interactions is estimated through in vitro cell assays. Variability in in vitro parameter...
A Sato et al.
Hypertension research : official journal of the Japanese Society of Hypertension, 22(1), 17-22 (1999-04-30)
There is increasing evidence for important cardiovascular effects of aldosterone via classical mineralocorticoid receptors in the heart. Administration of aldosterone with excess salt produces both cardiac hypertrophy and interstitial cardiac fibrosis in rats, and concomitant administration of potassium canrenoate at...
Neil Chapman et al.
Hypertension (Dallas, Tex. : 1979), 49(4), 839-845 (2007-02-21)
Spironolactone is recommended as fourth-line therapy for essential hypertension despite few supporting data for this indication. We evaluated the effect among 1411 participants in the Anglo-Scandinavian Cardiac Outcomes Trial-Blood Pressure Lowering Arm who received spironolactone mainly as a fourth-line antihypertensive...

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