Dirithromycin

Base Information

• Chemical Name: Dirithromycin
• CAS No.: 62013-04-1
• Molecular Formula: C₄₂H₇₈N₂O₁₄
• Molecular Weight: 835.086
• Hs Code.: 29419000
• European Community (EC) Number: 624-080-7
• DSSTox Substance ID: DTXSID10860773
• NCI Thesaurus Code: C47496
• Wikipedia: Dirithromycin
• Mol file: 62013-04-1.mol

Synonyms:Erythromycin,9-deoxo-11-deoxy-9,11-[imino[2-(2-methoxyethoxy)ethylidene]oxy]-, [9S(R)]-;ASE 136;Antibiotic AS-E 136;Dynabac;Noriclan;Valodin;

Chemical Property of Dirithromycin

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1.72E-35mmHg at 25°C
• Melting Point: 185 - 189oC
• Refractive Index: 1.533
• Boiling Point: 871.8 °C at 760 mmHg
• PKA: 9.0 in 66% aq dimethyl fluoride
• Flash Point: 481 °C
• PSA: 196.33000
• Density: 1.19 g/cm³
• LogP: 2.53050
• Storage Temp.: 2-8°C
• Solubility.: Very slightly soluble in water, very soluble in methanol and in methylene chloride
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 12
• Exact Mass: 834.54530517
• Heavy Atom Count: 58
• Complexity: 1300

Purity/Quality:

99% ^*data from raw suppliers

Dirithromycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn， Xi
• Hazard Codes: Xn,Xi
• Statements: 42/43-36/37/38
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C2C(C(C(CC(C(C(C(C(C(=O)O1)C)OC3CC(C(C(O3)C)O)(C)OC)C)OC4C(C(CC(O4)C)N(C)C)O)(C)O)C)NC(O2)COCCOC)C)(C)O
• Indications: It is applicable for patients over the age of 12 for the treatment of the following mild to moderate infections caused by sensitive bacteria: Acute exacerbation of chronic bronchitis: caused by Haemophilus influenzae, Moraxella catarrhalis, Streptococcus pneumoniae. Acute bronchitis: caused by Moraxella catarrhalis, Streptococcus pneumoniae. Community-acquired pneumonia: caused by Legionella pneumophila, Mycoplasma pneumoniae, Streptococcus pneumoniae. Pharyngitis and tonsillitis: caused by Streptococcus pyogenes. Simple skin and soft tissue infections: Staphylococcus aureus (methicillin sensitive strains), Streptococcus pyogenes caused.
• Description: Dirithromycin, an orally active oxazine derivative of erythromycin, is a secondgeneration macrolide antibiotic. It was first introduced in Spain for the treatment of respiratory tract, skin and soft tissue infections. It is safe and effective in treating acute bronchitis, acute bacterial exacerbation of chronic bronchitis, pneumonia, pharyngitis, and tonsillitis. Dirithromycin has been reported to have a similar antimicrobial spectrum and potency to erythromycin. However, compared to other macrolide antibiotics, dirithromycin has improved oral bioavailability, higher tissue permeability and longer duration of action. The once-daily therapy regiment is advantageous in terms of patient compliance and is a good alternative for patients who are unable to take penicillin. Dirithromycin is a macrolide antibiotic. It is a prodrug of erythromycylamine that has outstanding activity against Campylobacter. Dirithromycin is a group 3 agent with respect to its interaction with the cytochrome P450 (CYP) isoform 3A4, as it interferes poorly with CYP3A4 in vitro and generally does not alter drug metabolism in vivo.
• Uses: antihypertensive Dirithromycin is a macrolide antibiotic pro-drug of 9S-erythromycylamine, a close analogue of erythromycin in which the 9-keto group is replaced with an amino group in the S-configuration. Although erythromycylamine overcomes the acid instability of erythromycin, it is poorly absorbed following oral administration. Dirithromycin is formed by reacting erythromycylamine with an aldehyde to form a Schiff base which undergoes cyclisation to an oxazine with the C11-alcohol. Dirithromycin provides higher tissue levels and prolonged in vivo half-life by slowly releasing erythromycylamine. Semi-synthetic derivative of Erythromycin. Antibacterial
• Therapeutic Function: Antibacterial

Technology Process of Dirithromycin

There total 2 articles about Dirithromycin 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:

2-(2-methoxyethoxy)acetaldehyde dimethyl acetal → dirithromycin (62013-04-1,132561-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH, H₂O / acetonitrile / 8 h / Ambient temperature

2: acetonitrile / 10 h / Ambient temperature

With water; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1055/s-1993-26006

Reference yield:

erythromycylamine (26116-56-3) + 1-Methoxy-2-(2-methoxy-ethoxy)-ethanol → dirithromycin (62013-04-1,132561-92-3)

Guidance literature:

In acetonitrile; for 10h; Yield given; Ambient temperature;

DOI:10.1055/s-1993-26006

upstream raw materials:

erythromycylamine

Refernces

Generation of stable synthetic equivalents of unstable α-alkoxyacetaldehydes: An improved preparation of dirithromycin

10.1055/s-1993-26006

The research focuses on the development of a novel method for the in situ preparation of stable synthetic equivalents of unstable α-alkoxyacetaldehydes, with the specific application of improving the preparation of Dirithromycin (LY237216). The study addresses the challenges associated with the production and isolation of unstable α-alkoxyaldehydes, such as 2-methoxyethoxyacetaldehyde, which are prone to polymerization and decomposition. The researchers successfully synthesized the hemiacetal of 2-methoxyethoxyacetaldehyde by hydrolyzing its acetal precursor in aqueous acetonitrile solutions under mild conditions using p-toluenesulfonic acid as a catalyst. This hemiacetal served as a stable aldehyde equivalent, facilitating the efficient synthesis of Dirithromycin through its reaction with (9S)-erythromycylamine.