Anecortave acetate

Base Information

• Chemical Name: Anecortave acetate
• CAS No.: 7753-60-8
• Molecular Formula: C23H30O5
• Molecular Weight: 386.488
• European Community (EC) Number: 231-812-5
• NSC Number: 24345,15475
• UNII: Y0PC411K4T
• DSSTox Substance ID: DTXSID5046805
• Nikkaji Number: J195.929H
• Wikipedia: Anecortave_acetate
• Wikidata: Q4761567
• NCI Thesaurus Code: C171908
• Metabolomics Workbench ID: 149437
• ChEMBL ID: CHEMBL2106613
• Mol file: 7753-60-8.mol

Synonyms:4,9(11)-pregnadien-17alpha,21-diol-3,20-dione-21-acetate;anecortave acetate

Chemical Property of Anecortave acetate

Chemical Property:

• Vapor Pressure: 1.77E-14mmHg at 25°C
• Melting Point: 230-234°C
• Refractive Index: 1.572
• Boiling Point: 551.8 °C at 760 mmHg
• PKA: 12.47±0.60(Predicted)
• Flash Point: 188.4 °C
• PSA: 80.67000
• Density: 1.23 g/cm³
• LogP: 3.30170
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 386.20932405
• Heavy Atom Count: 28
• Complexity: 808

Purity/Quality:

99%, ^*data from raw suppliers

Anecortave ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1(CCC2C1(CC=C3C2CCC4=CC(=O)CCC43C)C)O
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)CC[C@@]43C)C)O
• Recent ClinicalTrials: Anecortave Acetate Injection to Treat Steroid-responsive Intraocular Pressure Increase in Cornea Transplant Patients
• Recent EU Clinical Trials: Evaluation of efficacy and safety of Intravitreal bevacizumab versus intravitreal bevacizumab combined with juxtascleral anecortave acetate for the treatment exudative age-related macular degeneration
• Description: Anecortave acetate, an angiogenesis inhibitor, was launched in Australia by Alcon for the treatment of age-related macular degeneration (AMD). AMD is the leading cause of untreatable blindness among people aged 65 to 74 years in the U.S. Worldwide, approximately 20 to 25 million people suffer from AMD, a disease that until recently was untreatable. Anecortave, an angiostatic steroid, down-regulates the expression MMP-2 and -9 to exert its antiangiogenic effects.
• Uses: As an angiostatic steroid, Anecortave Acetate can be used in treatment of macular degeneration.

Technology Process of Anecortave acetate

There total 33 articles about Anecortave acetate 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: 98.4%

21-chloro-17-hydroxy-pregna-4,9(11)-diene-3,20-dione (75868-48-3) + potassium acetate (127-08-2) → anecortave (7753-60-8)

Guidance literature:

With benzyltriethylammonium chloride; In N,N-dimethyl-formamide; at 90 ℃; for 3h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

Reference yield: 95.85%

hydrocortisone acetate (50-03-3) → anecortave (7753-60-8)

Guidance literature:

With pyridine; methanesulfonyl chloride; In N,N-dimethyl-formamide; at 50 - 82 ℃; for 2h;

Reference yield: 91.7%

17α-Hydroxy-21-iodopregna-4,9(11)-diene-3,20-dione (95816-38-9) → anecortave (7753-60-8)

Guidance literature:

17α-Hydroxy-21-iodopregna-4,9(11)-diene-3,20-dione; With potassium acetate; In N,N-dimethyl-formamide; at 65 ℃; for 2h; Inert atmosphere;

In water; N,N-dimethyl-formamide; for 0.5h; Inert atmosphere;

DOI:10.2174/1386207323666200219122644

upstream raw materials:

hydrocortisone acetate

21-acetoxy-16β-bromo-17-hydroxy-pregna-4,9(11)-diene-3,20-dione

21-acetoxy-17-hydroxy-11α-methanesulfonyloxy-pregn-4-ene-3,20-dione

Anecortave

Downstream raw materials:

Fludrocortisone

fludrocortisone acetate

9α-Fluor-11β-hydroxy-3,17-dioxo-androsten-4

9α-fluorocortisone

Refernces

• 1、 Huy, Luu D.,Diep, Nguyen T.,Vu, Tran K.,Savinova, Tatiana S.,Donova, Marina V.. "An efficient procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione". . p. 225 - 231. Retrieved 2020/04/27.
• 2、 -. "Synthesis method of 17-site side chain of steroidal drug". . . Retrieved 2018/06/26.