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S3378

Sigma-Aldrich

Spironolactone

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

Synonyme(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

Formule empirique (notation de Hill):
C24H32O4S
Numéro CAS:
52-01-7
Poids moléculaire :
416.57
Numéro CE :
200-133-6
Numéro MDL:
MFCD00082250
Code UNSPSC :
51111800
ID de substance PubChem :
24277736
Nomenclature NACRES :
NA.77

product name

Spironolactone, 97.0-103.0%

Pureté

97.0-103.0%

Pf

207-208 °C (lit.)

Solubilité

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

Chaîne SMILES 

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

Clé InChI

LXMSZDCAJNLERA-ZHYRCANASA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Notes préparatoires

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

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H351,H360FD,H373

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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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
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
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
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
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