Erythromycin, 14-hydroxy-6-O-methyl- CAS NO (110671-78-8) In Bulk Quantity

Erythromycin, 14-hydroxy-6-O-methyl-, with the Chemical Abstracts Service (CAS) number 110671-78-8, is a derivative of erythromycin, a macrolide antibiotic produced by the bacterium Saccharopolyspora erythraea. This compound is a semi-synthetic modification of erythromycin, featuring a hydroxyl group at the 14th carbon and a methyl group at the 6th position of the sugar moiety.

1. Chemical Structure Erythromycin, 14-hydroxy-6-O-methyl-, retains the characteristic macrolide ring structure of erythromycin, consisting of a macrocyclic lactone ring with several sugar moieties attached. The addition of a hydroxyl group at the 14th carbon and a methyl group at the 6th carbon alters the chemical properties and pharmacological activity of the molecule.

2. Semi-Synthetic Derivative This compound is a semi-synthetic derivative of erythromycin, produced through chemical modification of the parent compound. Semi-synthesis allows for the introduction of specific functional groups to improve pharmacokinetic properties, enhance antimicrobial activity, or reduce adverse effects.

3. Antibacterial Activity Erythromycin, 14-hydroxy-6-O-methyl-, retains the antibacterial activity characteristic of erythromycin and other macrolide antibiotics. It inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit, thereby preventing peptide bond formation and inhibiting bacterial growth. This mechanism of action makes it effective against a wide range of Gram-positive and some Gram-negative bacteria.

4. Spectrum of Activity Like erythromycin, this derivative exhibits activity against Gram-positive bacteria, including Streptococcus pneumoniae, Streptococcus pyogenes, Staphylococcus aureus, and Corynebacterium species. It is also active against certain Gram-negative bacteria, such as Haemophilus influenzae and Moraxella catarrhalis, as well as atypical pathogens like Mycoplasma pneumoniae and Legionella pneumophila.

5. Pharmacokinetics Erythromycin, 14-hydroxy-6-O-methyl-, possesses pharmacokinetic properties similar to erythromycin, including oral bioavailability, tissue distribution, and metabolism. It is metabolized in the liver and excreted primarily in the bile. The introduction of hydroxyl and methyl groups may influence its pharmacokinetic profile compared to erythromycin.

6. Clinical Use This derivative is used in the treatment of bacterial infections caused by susceptible organisms. It is indicated for respiratory tract infections, skin and soft tissue infections, genital infections, and other bacterial diseases. However, its use may be limited by bacterial resistance and adverse effects, such as gastrointestinal disturbances and QT interval prolongation.

7. Drug Interactions As with erythromycin, this derivative may interact with other medications, particularly those metabolized by cytochrome P450 enzymes. Concomitant use with drugs that inhibit or induce these enzymes can affect the plasma levels and efficacy of both erythromycin and co-administered drugs, leading to potential adverse effects or therapeutic failure.

8. Resistance The emergence of bacterial resistance to macrolide antibiotics, including erythromycin and its derivatives, is a significant concern in clinical practice. Bacterial resistance mechanisms may include efflux pumps, ribosomal mutations, and enzymatic inactivation. Combination therapy and prudent antibiotic use are strategies to mitigate resistance.

9. Safety Profile Erythromycin, 14-hydroxy-6-O-methyl-, shares the safety profile of erythromycin, with potential adverse effects including gastrointestinal disturbances, hepatotoxicity, allergic reactions, and QT interval prolongation. Patients with pre-existing liver disease or cardiac conditions may be at increased risk of adverse effects and require close monitoring.

10. Conclusion Erythromycin, 14-hydroxy-6-O-methyl-, is a semi-synthetic derivative of erythromycin with antibacterial activity against a wide range of pathogens. While it shares the pharmacological properties and clinical indications of erythromycin, its semi-synthetic nature may offer advantages in terms of pharmacokinetics and antimicrobial potency. However, bacterial resistance and potential adverse effects should be considered when prescribing this antibiotic in clinical practice.