Anecortave Acetate (H6) （cas 7753-60-8）
Comprehensive Information Table
| Category | Details |
|---|---|
| CAS Number | 7753-60-8 |
| Synonyms | Retaane, Anecortave, 21-Acetoxypregna-4,9(11)-dien-17α-ol-3,20-dione, Hydrocortisone Acetate EP Impurity E |
| Chemical Formula | C₂₃H₃₀O₅ |
| Molecular Weight | 386.48 g/mol |
| EINECS Number | 231-812-5 |
| Melting Point | 230–234°C |
| Solubility | Slightly soluble in chloroform and methanol; practically insoluble in water |
| Appearance | White to off-white powder |
| pKa | 12.47 ± 0.60 (predicted) |
| Optical Activity | [α]²⁵/D +117° (c = 1.0 in CHCl₃) |
| Bulk Density | ~640 kg/m³ |
| Refractive Index | 1.56 (C=10, H₂O) |
Key Applications & Pharmacological Properties
- Ocular Anti-Angiogenic Agent:
- Inhibits pathological retinal angiogenesis by targeting vascular endothelial growth factor (VEGF) and modulating matrix metalloproteinases (MMPs) 610.
- Used in research for age-related macular degeneration (AMD) and diabetic retinopathy models 29.
- Anti-Inflammatory & Immunosuppressive:
- Suppresses microglial activation and cytokine release (e.g., TNF-α, IL-6) in neuroinflammatory conditions 10.
- Research Tool:
- Investigated for its role in steroidogenesis and as a potential therapeutic for corneal neovascularization 9.
Synthesis & Production
- Chemical Synthesis:
- Hydroxylation: Selective 17α-hydroxylation of pregnenolone via microbial biotransformation (e.g., Rhodococcus equi) 3.
- Acetylation: Introduction of the 21-acetate group using acetic anhydride in alkaline conditions.
- Biological Production:
- Derived from cholesterol via pregnenolone in adrenal glands or ovaries.
Quality Control & Safety
| Parameter | Specifications |
|---|---|
| Purity | ≥98% (HPLC) |
| Impurities | ≤0.5% total organic impurities |
| Heavy Metals | ≤10 ppm (Pb, Cd, Hg) |
| Toxicity | – LD₅₀ (mouse, oral): >5000 mg/kg – Irritation: Eyes, respiratory system, skin |
| Handling Precautions | Wear gloves/face shields; avoid inhalation. Store at -20°C in airtight containers. |
Regulatory Status
- Approved Uses:
- Veterinary: Investigational use in ocular diseases in animal models.
- Human Use: Not approved; restricted to research applications.
- Restrictions:
- Classified as a hazardous chemical (EU CLP: H315, H319).
- Requires controlled storage due to light/temperature sensitivity.
Research & Development
- Novel Formulations:
- Nanoparticle Suspensions: Enhance ocular bioavailability for retinal diseases 10.
- Controlled-Release Implants: Sustain therapeutic levels in choroidal neovascularization.
- Combination Therapies:
- Synergistic effects with anti-VEGF agents (e.g., bevacizumab) in AMD treatment 9.
For detailed toxicology data or synthesis protocols, consult regulatory databases (e.g., FDA, EMA) or specialized pharmacological references.
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