Anecortave

Base Information

• Chemical Name: Anecortave
• CAS No.: 10184-70-0
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.451
• UNII: R5Y8O51589
• DSSTox Substance ID: DTXSID70144268
• Nikkaji Number: J1.914.018K
• Metabolomics Workbench ID: 153134
• ChEMBL ID: CHEMBL2348782
• Mol file: 10184-70-0.mol

Synonyms:17,21-dihydroxypregna-4,9(11)-diene-3,20-dione;AL 4940;AL-4940;Anecortave

Chemical Property of Anecortave

Chemical Property:

• Melting Point: 231-233 °C(Solv: tetrahydrofuran (109-99-9))
• Boiling Point: 540.4±50.0 °C(Predicted)
• PKA: 12.52±0.60(Predicted)
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated)
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 344.19875937
• Heavy Atom Count: 25
• Complexity: 705

Purity/Quality:

98%,99%, ^*data from raw suppliers

21-DesacetylAnecortave ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2=CCC4(C3CCC4(C(=O)CO)O)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3C2=CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C
• Recent EU Clinical Trials: A Study of the Safety and Efficacy of Anecortave Acetate for Treatment of Steroid
• Uses: 17-Desacetyl Anecortave is a Anecortave Acetate (A637640). It displays glucocorticoid and mineralocorticoid receptor binding activities.

Technology Process of Anecortave

There total 12 articles about Anecortave which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 37.0%

anecortave (7753-60-8) → Anecortave (10184-70-0)

Guidance literature:

With potassium hydroxide; In methanol;

Reference yield:

Nicotinic acid (8S,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (119669-94-2) → Anecortave (10184-70-0)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1021/ja00246a058

Reference yield:

Nicotinic acid (8S,9R,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-9-chloro-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (108674-98-2) → Anecortave (10184-70-0)

Guidance literature:

Multi-step reaction with 2 steps

1: AgBF₄ / acetone

2: K₂CO₃ / methanol

With silver tetrafluoroborate; potassium carbonate; In methanol; acetone;

DOI:10.1021/ja00246a058

upstream raw materials:

anecortave

21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregna-5,9⁽¹¹⁾-dien-17-ol

Nicotinic acid (8S,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Nicotinic acid (8S,9R,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-9-chloro-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Downstream raw materials:

androst-4,9⁽¹¹⁾-dien-3,17-dione

anecortave

hydroxy-17β androstadiene-4,9(11) one-3,7

Refernces

• 1、 Bernstein et al.. "-". . p. 4830. Retrieved 1953.
• 2、 -. "HETERODIMER COMPOSITIONS AND METHODS FOR THE TREATMENT OF OCULAR DISORDERS". Paragraph 0435-0436. . Retrieved 2021/11/13.
• 3、 -. "NON-HORMONAL STEROID MODULATORS OF NF-?B FOR TREATMENT OF DISEASE". Page/Page column 48. . Retrieved 2011/10/31.