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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 key

LXMSZDCAJNLERA-ZHYRCANASA-N

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 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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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.

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.

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
MKCQ0644
MKCN6806
MKCK8547
MKCG6303
MKCD7812

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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
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
P Moghetti et al.
The Journal of clinical endocrinology and metabolism, 84(4), 1250-1254 (1999-04-13)
GnRH agonists (GnRHa) have recently been proposed for the treatment of hirsutism in women with the polycystic ovary syndrome (PCOS). As most of these subjects have increased androgen secretion from both ovaries and adrenal glands, the association of GnRHa with
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
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