Lexithromycin

Base Information

• Chemical Name: Lexithromycin
• CAS No.: 53066-26-5
• Molecular Formula: C₃₈H₇₀N₂O₁₃
• Molecular Weight: 762.979
• UNII: 7QKO29734U
• Nikkaji Number: J2.258.404I
• NCI Thesaurus Code: C87760
• ChEMBL ID: CHEMBL1774286
• Mol file: 53066-26-5.mol

Synonyms:erythromycin A methoxime

Chemical Property of Lexithromycin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 824.6°Cat760mmHg
• PKA: 13.19±0.70(Predicted)
• Flash Point: 452.5°C
• PSA: 198.43000
• Density: 1.26g/cm³
• LogP: 2.21890
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 762.48779029
• Heavy Atom Count: 53
• Complexity: 1230

Purity/Quality:

99% ^*data from raw suppliers

Lexithromycin 98.80% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C(C(C(=NOC)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
• Isomeric SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](/C(=N/OC)/[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
• Description: Lexithromycin is a semisynthetic antibiotic derived from erythromycin . Lexithromycin has improved absorption in vivo over erythromycin due to increased hydrophopicity and pH stability. As with other macrolides, lexithromycin prevents protein synthesis by binding the ribosome at the polypeptide exit tunnel. Formulations containing lexithromycin were tested in clinical trials as treatment for HIV but were discontinued.
• Uses: Lexithromycin is an early semi-synthetic erythromycin, prepared by reaction of the 9-keto moiety to methyl oxime. The structural change improves the pH stability profile and hydrophobicity of lexithromycin for better in vivo absorption. This same rationale was used to greater effect with roxithromycin and, as a result, lexithromycin was quickly superseded and has not been not extensively studied. Like all tetracyclines, lexithromycin shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis. Lexithromycin is a semi-synthetic erythromycin with improved pH stability and hydrophobicity. It is used in compositions and methods for treating viral infections.

Technology Process of Lexithromycin

There total 1 articles about Lexithromycin 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:

N-methoxylamine hydrochloride (593-56-6) + erythromycin A (114-07-8,86832-48-6,150577-53-0) → (E)-9-deoxo-9-methoxyiminoerythromycin A (53066-26-5,118244-58-9,118244-59-0,132830-05-8)

Guidance literature:

In pyridine; 1.) 5 deg C, 120 h; 2.) r.t., 24 h;

Reference yield: 93.0%

(E)-9-deoxo-9-methoxyiminoerythromycin A (53066-26-5,118244-58-9,118244-59-0,132830-05-8) + formyl acetic anhydride (2258-42-6) → (E)-2'-O-4''-O-diformyl-9-deoxo-9-methoxyiminoerythromycin A (108394-37-2,127420-14-8)

Guidance literature:

With dmap; In dichloromethane; for 5h; Ambient temperature;

Reference yield:

(E)-9-deoxo-9-methoxyiminoerythromycin A (53066-26-5,118244-58-9,118244-59-0,132830-05-8) → C41H75BrN2O14

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / Ambient temperature

2: 2,6-lutidine / dimethylformamide / 6 h

With 2,6-dimethylpyridine; dmap; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

N-methoxylamine hydrochloride

erythromycin A

Downstream raw materials:

(E)-2'-O-4''-O-diformyl-9-deoxo-9-methoxyiminoerythromycin A

(E)-11-O-(2-dimethylaminoethoxy)methyl-9-deoxo-9-methoxyiminoerythromycin A

Refernces