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

Properties

• product name: Spironolactone, 97.0-103.0%
• Assay: 97.0-103.0%
• mp: 207-208 °C (lit.)
• solubility: chloroform: complete 50 mg/ml, clear, faintly yellow
• 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)

Description

Application

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

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 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.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H351,H360FD,H373
• Precautionary Statements: P202 - P260 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 2 - Repr. 1B - STOT RE 2
• Storage Class Code: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves