Эритралозамин

Description

Erythralosamine is a product of acid degradation of the macrolide antibiotic erythromycin, which does not have antibacterial activity. Chemical formula C31H53NO8, English name erythralosamine, CAS number 546-57-6. According to the nomenclature - 5-O-desosaminyl-10,11-anhydroerythronolide A-6,9;9,12-spiroketal, also known as erythromycin spiroketal 6,9,9,12 and as impurity I of erythromycin according to the European Pharmacopoeia.

Substance class

Refers to the products of intramolecular cyclization of erythromycin, formed during the degradation of the macrolactone ring in an acidic environment. During acidic decomposition, intramolecular cyclization occurs with the formation of a spiroketal fragment from the erythronolide lactone system, while the desosamine sugar residue at position C5 is retained, and the mycarose residue is lost.

Basic Attributes

• CAS No.: 546-57-6
• Chemical formula: C31H53NO8
• Molecular weight: 567.759
• Exact weight: 539.346
• PSA Specifications: 107
• XLogP3: 2.7

Physico-chemical characteristics

• Density: 1.18 ± 0.1 g/cm3 (predicted value)
• Melting point: 207–208 °C

Significance as a pharmacopoeial impurity

Erythralosamine is formed as one of the main products of the acidic decomposition of erythromycin, in particular when the drug is stored under unfavorable conditions or when passing through the acidic environment of the stomach. It is officially recognized as impurity I of erythromycin according to the European Pharmacopoeia and other pharmacopoeial standards, which makes it a mandatory reference substance for the validation of methods for chromatographic control of the purity of erythromycin and related antibiotics.

Scope of application

Used exclusively as an analytical standard for the quantitative determination of erythromycin degradation products by HPLC in pharmaceutical production and quality control. It does not have its own antibacterial activity and is not considered as an independent medicinal component, but serves as an indicator of the degree of decomposition of the active antibiotic in the finished dosage form.

Storage and transportation

Store in an airtight container in a cool, dry place, protected from direct light and moisture. Transport as an analytical standard in compliance with the requirements for the transport of laboratory reagents sensitive to atmospheric humidity.

Place among macrolide degradation products

Erythralosamine is one of several known products of the acid degradation of erythromycin, along with anhydroerythromycin and other spiroketal and dehydrated forms, resulting from the destruction of the labile macrolactone ring in an acidic environment. The presence of such impurities in the finished drug substance is strictly controlled by pharmacopoeial methods, since their accumulation indicates a violation of the storage conditions of the drug or insufficient protection from acid hydrolysis during the production of acid-resistant dosage forms of erythromycin.