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Merck

S3378

Spironolactone

97.0-103.0% (HPLC), powder, aldosterone receptor antagonist

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

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About This Item

Empirical Formula (Hill Notation):
C24H32O4S
CAS Number:
52-01-7
Molecular Weight:
416.57
NACRES:
NA.77
PubChem Substance ID:
24277736
UNSPSC Code:
51111800
EC Number:
200-133-6
MDL number:
MFCD00082250

Key Documents

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Product Name

Spironolactone, 97.0-103.0%

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

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

assay

97.0-103.0%

mp

207-208 °C (lit.)

solubility

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

Quality Level

200

Gene Information

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

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Application

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

Biochem/physiol Actions

Spironolactone is a competitive aldosterone receptor antagonist. Used as potassium sparing diuretic.
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.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

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

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Carc. 2 - Repr. 1B - STOT RE 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4523
MKCW2857
MKCR9630
MKCQ0644
MKCN6806

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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
B Pitt et al.
The New England journal of medicine, 341(10), 709-717 (1999-09-02)
Aldosterone is important in the pathophysiology of heart failure. In a doubleblind study, we enrolled 1663 patients who had severe heart failure and a left ventricular ejection fraction of no more than 35 percent and who were being treated with
C A Farquharson et al.
Circulation, 101(6), 594-597 (2000-02-15)
The RALES study showed that spironolactone, added to conventional therapy for chronic heart failure, dramatically reduced mortality. We tested the hypothesis that this benefit was partially due to improvement in endothelial function and/or to amplified suppression of the vascular renin-angiotensin
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
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
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