Canrenone (CAS 976-71-6)

Canrenone Ingredients

Canrenone (Canrenone) Comprehensive Information

​Chemical Properties

1. ​Basic Parameters
   • ​Chemical Formula: C₂₂H₂₈O₃
   • ​Molecular Weight: 340.46
   • ​CAS Number: 976-71-6
   • ​EINECS Number: 213-554-5
   • ​Melting Point: 158–160°C
   • ​Boiling Point: 416.25°C (estimated)
   • ​Density: 1.1236 (estimated)
   • ​Solubility: Insoluble in water; soluble in DMSO (20 mg/mL) and ethanol (≥58.6 mg/mL)
   • ​Appearance: Pale yellow to pale green solid
   • ​Optical Activity: [α]²⁵/D +17 to +24° (c = 1 in chloroform-d)
   • ​Water Solubility: 272.4 µg/L (25°C)
   • ​Storage Temperature: Room temperature (protected from light)
2. ​Structural Features
   A steroid lactone derivative of spironolactone, acting as a mineralocorticoid receptor antagonist. Its structure includes a γ-lactone ring fused to a pregnadiene system, enabling potent aldosterone antagonism.

​Pharmacological Actions and Clinical Applications

1. ​Mechanism of Action
   • ​Aldosterone Antagonism: Competitively binds to mineralocorticoid receptors in the kidneys, inhibiting sodium reabsorption and potassium excretion.
   • ​Anti-inflammatory: Reduces oxidative stress and fibrosis in vascular and renal tissues.
2. ​Indications
   • ​Hypertension: Lowers blood pressure by counteracting aldosterone-driven sodium retention 10.
   • ​Heart Failure: Improves outcomes in heart failure models by reducing vascular stiffness and fibrosis 38.
   • ​Diabetes-Related Complications: Mitigates renal fibrosis and endothelial dysfunction in diabetic models.
3. ​Dosage Forms
   • ​Oral Tablets: 25–100 mg/day for hypertension or heart failure.
   • ​Injectable Solutions: For acute management of severe hypertension.

​Safety and Precautions

1. ​Adverse Effects
   • ​Hyperkalemia: Common due to potassium retention; monitor serum potassium levels.
   • ​Gynecomastia: Androgen receptor modulation may cause breast tissue growth in males.
2. ​Contraindications
   • Severe renal impairment (eGFR <30 mL/min/1.73m²).
   • Pregnancy or lactation (risk of fetal harm).
3. ​Drug Interactions
   • ​ACE Inhibitors/ARBs: Synergistic risk of hyperkalemia.
   • ​NSAIDs: Reduced renal perfusion may exacerbate potassium retention.

​Manufacturing and Quality Control

1. ​Synthesis
   Produced via cyclization of 17α-carboxyethyl-17β-hydroxyandrost-4-en-3-one lactone using chloranil as an oxidizing agent 7.
2. ​Analytical Standards
   • ​HPLC: C18 column with methanol-water (60:40) mobile phase; UV detection at 240 nm.
   • ​Impurity Limits: Total impurities ≤0.5% of main peak area.

​Research and Market

1. ​Scientific Use
   • ​Cardiovascular Research: Models for studying aldosterone’s role in vascular remodeling.
   • ​Cancer Therapy: Investigated for inhibiting epithelial-mesenchymal transition (EMT) in breast cancer cells 5.
2. ​Market Overview
   • ​Price: ~50–100 per gram (research-grade).

​Regulatory and Storage

• ​Regulatory Status: Approved for veterinary and human use in some countries; classified as a prescription drug.
• ​Stability: Stable for 24 months under recommended conditions (cool, dry place).

For detailed toxicological data or clinical trial protocols, consult specialized pharmacological references.