Dexamethasone acefurate

Base Information

• Chemical Name: Dexamethasone acefurate
• CAS No.: 83880-70-0
• Molecular Formula: C29H33 F O8
• Molecular Weight: 528.57
• UNII: W4N6E1T46B
• DSSTox Substance ID: DTXSID3022900
• Wikipedia: Dexamethasone_acefurate
• Wikidata: Q27292297
• NCI Thesaurus Code: C77413
• ChEMBL ID: CHEMBL1697787
• Mol file: 83880-70-0.mol

Synonyms:Dexamethasone acefurate;Sch 31353;83880-70-0;UNII-W4N6E1T46B;W4N6E1T46B;Dexamethasone acefurate [USAN:INN];SCH-31353;[(8S,9R,10S,11S,13S,14S,16R,17R)-17-(2-acetyloxyacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate;9-Fluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate 17-(2-furaoate);9-Fluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate 17-(2-furoate);SCHEMBL139744;CHEMBL1697787;DTXSID3022900;C29H33FO8;CHEBI:135819;Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9-fluoro-17-((2-furanylcarbonyl)oxy)-11-hydroxy-16-methyl-, (11 beta,16 alpha)-;Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9-fluoro-17-((2-furanylcarbonyl)oxy)-11-hydroxy-16-methyl-, (11beta,16alpha)-;Dexamethasone acefurate (USAN/INN);C29-H33-F-O8;DEXAMETHASONE ACEFURATE [INN];DEXAMETHASONE ACEFURATE [USAN];D02591;Q27292297;(11beta,16alpha)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl furan-2-carboxylate;PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-9-FLUORO-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.)-

Chemical Property of Dexamethasone acefurate

Chemical Property:

• Vapor Pressure: 9.81E-18mmHg at 25°C
• Boiling Point: 649.1°C at 760 mmHg
• PKA: 12.88±0.70(Predicted)
• Flash Point: 346.4°C
• PSA: 120.11000
• Density: 1.33g/cm³
• LogP: 3.92420
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 528.21594617
• Heavy Atom Count: 38
• Complexity: 1130

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)COC(=O)C)OC(=O)C5=CC=CO5)C)O)F)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)COC(=O)C)OC(=O)C5=CC=CO5)C)O)F)C
• Recent EU Clinical Trials: Repeat dose steroid to prevent pain relapse after Total Knee Arthroplasty in patients with high pain response - A randomized blinded placebo-controlled trial
• Uses: Steroid (topical).

Technology Process of Dexamethasone acefurate

There total 4 articles about Dexamethasone acefurate 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: 79.0%

Furan-2-carboxylic acid (8S,9R,10S,13S,14S,16R,17R)-17-(2-acetoxy-acetyl)-9-fluoro-10,13,16-trimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (83880-69-7) → 9α-fluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 17-(2'-furoate) 21-acetate (83880-70-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; N,N-dimethyl-formamide; for 0.333333h;

DOI:10.1021/jm00392a010

Reference yield: 2.0%

2-furancarbonyl chloride (527-69-5) + betamethasone (1177-87-3) → 9α-fluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 17-(2'-furoate) 21-acetate (83880-70-0)

Guidance literature:

With 4-pyrrolidin-1-ylpyridine; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1021/jm00392a010

Reference yield:

2-furancarbonyl chloride (527-69-5) → 9α-fluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 17-(2'-furoate) 21-acetate (83880-70-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / 4-(dimethylamino)pyridine (4-DMAP) / CH₂Cl₂ / 72 h

2: 79 percent / NaBH₄ / dimethylformamide; methanol; H₂O / 0.33 h

With dmap; sodium tetrahydroborate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00392a010

upstream raw materials:

2-furancarbonyl chloride

betamethasone

Furan-2-carboxylic acid (8S,9R,10S,13S,14S,16R,17R)-17-(2-acetoxy-acetyl)-9-fluoro-10,13,16-trimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

9α-fluoro-17α,21-dihydroxy-16α-methyl-1,4-pregnadiene-3,11,20-trione 21-acetate

Refernces