992-62-1

Basic information

• Product Name: N-DEMETHYL ERYTHROMYCIN A
• Synonyms: Clarithromycin Impurity R (10 mg) (N-desmethyl erythromycin A);DeMethylerythroMycin A, N-;N-Demethylerithromycyn;N-Desmethyl Erythromycin A;N-DEMETHYL ERYTHROMYCIN A;Demethylerythromycin;Des-N-methylerythromycin;N-Demethyl-erythromycin
• CAS NO: 992-62-1
• Molecular Formula: C₃₆H₆₅NO₁₃
• Molecular Weight: 719.904
• EINECS: 241-424-8
• Product Categories: Various Metabolites and Impurities;Metabolites & Impurities
• Mol File: 992-62-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 142-144°C
• Boiling Point: 818.1°Cat760mmHg
• Flash Point: 448.6°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 5.23E-31mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.09±0.70(Predicted)
• CAS DataBase Reference: N-DEMETHYL ERYTHROMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: N-DEMETHYL ERYTHROMYCIN A(992-62-1)
• EPA Substance Registry System: N-DEMETHYL ERYTHROMYCIN A(992-62-1)

Safety Data

• Hazardous Substances Data: 992-62-1(Hazardous Substances Data)

Usage

Description

N-Demethyl Erythromycin A is a minor co-metabolite of erythromycin, produced by the bacterium Saccharopolyspora erythreae. It is a derivative of the well-known antibiotic erythromycin, with a modified structure that results in a significantly reduced spectrum of antibiotic activity compared to erythromycins A, B, and C.

Uses

Used in Pharmaceutical Industry:
N-Demethyl Erythromycin A is used as an impurity in the production of erythromycin, an antibiotic with a broad-spectrum of activity. As Erythromycin EP Impurity B, it is important for quality control and ensuring the purity of erythromycin products. The presence of N-Demethyl Erythromycin A in erythromycin formulations is closely monitored to maintain the safety and efficacy of the antibiotic.
Although N-Demethyl Erythromycin A exhibits a very narrow spectrum of antibiotic activity and is much less active than erythromycins A, B, and C, it may still have potential applications in research and development for new antibiotics or as a starting material for the synthesis of other macrolide derivatives with improved properties. However, its primary use is in the pharmaceutical industry for quality control purposes in erythromycin production.

InChI:InChI=1/C36H65NO13/c1-13-24-36(10,44)29(40)19(4)26(38)17(2)15-34(8,43)31(50-33-27(39)23(37-11)14-18(3)46-33)20(5)28(21(6)32(42)48-24)49-25-16-35(9,45-12)30(41)22(7)47-25/h17-25,27-31,33,37,39-41,43-44H,13-16H2,1-12H3

Upstream product

• 114-07-8 erythromycin 
• 81103-09-5 2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A 

Downstream Products

• 1192304-43-0 N'-benzyl-2'-O,3'-N-(carbonimidoyl)-3'-N-demethyl-erythromycin A 
• 127955-44-6 de(N-methyl)-N-formylerythromycin A 
• 677726-20-4 C₄₀H₆₉NO₁₃ 
• 142635-07-2 3'-N-demethyl-11-oxo-3'-N-(phenylsulfonyl)anhydroerythromycin A 
• 142635-08-3 9,10-didehydro-3'-N-demethyl-9-deoxo-12-deoxy-9,12-epoxy-11-oxo-3'-N-(phenylsulfonyl)erythromycin A 
• 142655-94-5 3'-N-demethyl-3'-N-(phenylsulfonyl)anhydroerythromycin A 
• 110480-13-2 Idremcinal 
• 81103-09-5 2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A 
• 992-65-4 erythromycin A N-oxide 
• 114-07-8 erythromycin 
• 98641-05-5 de(N-methyl)-8,9-anhydroerythromycin A 6,9-hemiacetal 
• 142635-06-1 3'-N-demethyl-3'-N-(phenylsulfonyl)erythromycin A 

Relevant articles and documents

Modeling interactions of erythromycin derivatives with ribosomes

Using a method of static simulation, a series of erythromycin A analogs was designed with aldehyde functions introduced instead of one of the methyl substituents in the 3′-N-position of the antibiotic that was potentially capable of forming a covalent bond with an amino group of one of the nucleotide residues of the 23S rRNA in the ribosomal exit tunnel. Similar interaction is observed for antibiotics of the tylosin series, which bind tightly to the large ribosomal subunit and demonstrate high antibacterial activity. Binding of novel erythromycin derivatives with the bacterial ribosome was investigated with the method of fluorescence polarization. It was found that the erythromycin analog containing a 1-methyl-3oxopropyl group in the 3′-N-position demonstrates the best binding. Based on the ability to inhibit protein biosynthesis, it is on the same level as erythromycin, and it is significantly better than desmethyl-erythromycin. Molecular dynamic modeling of complexes of the derivatives with ribosomes was conducted to explain the observed effects.

2'-O,3'-N-BRIDGED MACROLIDES

Novel 2 ' -O, 3 ' -/V-bridged macrolides useful in treatment of inflammatory diseases. More particularly, the invention relates to 2 ' -O, 3 ' -/V-bridged 14- membered macrolides and to 2 ' - O, 3 ' -/V-bridged 15-membered azalide macrolides useful in treatment of neutrophil dominated inflammatory diseases resulting from neutrophilic infiltration and/or diseases associated with altered cellular functionality of neutrophils, to intermediates for their preparation, to the methods for their preparation, to their use as therapeutic agents, and to salts thereof.

MACROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME

The present invention provides macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents.