118058-74-5

Basic information

• Product Name: 3-O-Decladinosyl-6-O-Methylerythronolide A
• Synonyms: 3-O-De(2,6-dideoxy-3-C-Methyl-3-O-Methyl-α-L-ribo-hexopyranosyl)-6-O-MethylerythroMycin;3-O-Decladinosyl-6-O-Methylerythronolide A;5-O-DesosaMinyl-6-O-Methylerythronolide A;De(cladinosyl) ClarithroMycin;DesclarithoMycin;Des(cladinosyl) Clarithromycin;Clarithromycin EP Impurity I;(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-4,12,13-trihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecan
• CAS NO: 118058-74-5
• Molecular Formula: C₃₀H₅₅NO₁₀
• Molecular Weight: 589.7584
• Product Categories: Chiral Reagents;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 118058-74-5.mol
• Article Data: 32

Chemical Properties

• Melting Point: 158-160 °C
• Boiling Point: 708.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.10±0.70(Predicted)
• CAS DataBase Reference: 3-O-Decladinosyl-6-O-Methylerythronolide A(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-Decladinosyl-6-O-Methylerythronolide A(118058-74-5)
• EPA Substance Registry System: 3-O-Decladinosyl-6-O-Methylerythronolide A(118058-74-5)

Safety Data

• Hazardous Substances Data: 118058-74-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 118058-74-5 differently. You can refer to the following data:
1. De(cladinosyl) Clarithromycin is an impurity of Clarithromycin (C559750). De(cladinosyl) Clarithromycin showed significantly potent antibacterial activity against community acquired respiratory pathogens.
2. De(cladinosyl) Clarithromycin (Clarithromycin EP Impurity I) is an impurity of Clarithromycin (C559750). De(cladinosyl) Clarithromycin showed significantly potent antibacterial activity against community acquired respiratory pathogens.

Upstream product

• 81103-11-9 clarithromycin 
• 143353-81-5 3-Ode-[(2,6-dideoxy-3-methyl-3-O-methyl-α-L-ribohexopyranosyl)oxy]-6-O-methylerythromycin 2￠-acetate 

Downstream Products

• 875475-90-4 C₃₈H₅₇NO₁₂ 

Relevant articles and documents

A novel series of 11-O-carbamoyl-3-O-descladinosyl clarithromycin derivatives bearing 1,2,3-triazole group: Design, synthesis and antibacterial evaluation

A series of novel 11-O-carbamoyl-3-O-descladinosyl clarithromycin derivatives bearing the 1,2,3-triazole group were designed, synthesized, and evaluated for their in vitro antibacterial activity. The antibacterial results indicated that most of the target compounds not only increased their activity against resistant bacterial strains, but also partially retained the activity against sensitive bacterial strains compared with clarithromycin. Among them, 13d had the best antibacterial activity against resistant strains, including Streptococcus pneumoniae B1 expressing the ermB gene (16 μg/mL), Streptococcus pneumoniae AB11 expressing the mefA and ermB genes (16 μg/mL) and Streptococcus pyogenes R1 (16 μg/mL), showing >16, 8 and 16-fold higher activity than that of CAM, respectively. Moreover, 13d and 13g exhibited the best antibacterial activity against sensitive bacterial strains, including Staphylococcus aureus ATCC25923 (4 μg/mL) and Bacillus Subtilis ATCC9372 (1 μg/mL). The MBC results showed that the most promising compounds 13d and 13g exhibited antibacterial activity through bacteriostatic mechanism, while the time-kill kinetic experiment revealed bactericidal kinetics of 13g from microscopic point of view. In vitro antibacterial experiments and molecular docking results further confirmed that it was feasible to our initial design strategy by modifying the C-3 and C-11 positions of clarithromycin to increase the activity against resistant bacteria.

Synthesis and antibacterial evaluation of novel 11-O-carbamoyl clarithromycin ketolides

A series of novel 11-O-carbamoyl clarithromycin ketolides were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed improved activity compared with references against erythromycin-resistant S. pneumoniae A22072 expressing the mef gene, S. pneumoniae B1 expressing the erm gene and S. pneumoniae AB11 expressing the mef and erm genes. In particular, compounds 9, 18, 19 and 22 showed the most potent activity against erythromycin-resistant S. pneumoniae A22072 with the MIC values of 0.5?μg/mL. Furthermore, compounds 11, 18, 19, 24 and 29 were also found to exhibit favorable antibacterial activity against erythromycin-susceptible S. pyogenes with the MIC values of 0.125–1?μg/mL, and moderate activity against erythromycin-susceptible S. aureus ATCC25923 and B. subtilis ATCC9372.

Design, synthesis and antibacterial evaluation of novel C-11, C-9 or C-2′-substituted 3-O-descladinosyl-3-ketoclarithromycin derivatives

A novel series of 3-O-descladinosyl-3-keto-clarithromycin derivatives, including 11-O-carbamoyl-3-O-descladinosyl-3-keto-clarithromycin derivatives and 2′,9(S)-diaryl-3-O-descladinosyl-3-keto-clarithromycin derivatives, were designed, synthesized and eval

Synthesis and antibacterial activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2- enyl)-10, 11-anhydroclarithromycin derivatives

An allyl group was attached to 3-keto function of ketolides in the presence of allyl bromide and KOtBu. Consequently, the Heck reaction of the resulting 2, 3-dehydro-3-O-allyl-10, 11-anhydroclarithromycin derivatives, in the presence of palladium (II) acetate and tri(o-tolyl)phosphine, afforded a 3-O-(3-aryl-E-prop-2-enyl) sidechain, not the previously reported 3-O-(3-aryl-Z-prop-1-enyl) sidechain. The results suggested that some steric factors in Β-hydrogen elimination might regulate the isomerization. The activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2-enyl)-10, 11-anhydroclarithromycin derivatives was low.

Synthesis and antibacterial evaluation of novel 11-O-aralkylcarbamoyl-3-O-descladinosylclarithromycin derivatives

A series of novel 11-O-aralkylcarbamoyl-3-O-descladinosylclarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed potent activity against erythromycin-susceptible S. pyogenes, erythromycin-resistant S. pneumoniae A22072 expressing the mef gene and S. pneumoniae AB11 expressing the mef and erm genes. Besides, most of the target compounds exhibited moderate activity against erythromycin-susceptible S. aureus ATCC25923 and B. subtilis ATCC9372. In particular, compounds 11a, 11b, 11c, 11e, 11f and 11h were found to exert favorable antibacterial activity against erythromycin-susceptible S. pyogenes with the MIC values of 0.015–0.125 μg/mL. Furthermore, compounds 10e, 11a, 11b and 11c showed superior activity against erythromycin-resistant S. pneumoniae A22072 with the MIC values of 0.25–0.5 μg/mL. Additionally, compound 11c was the most effective against all the erythromycin-resistant S. pneumoniae strains (A22072, B1 and AB11), exhibiting 8-, 8- and 32-fold more potent activity than clarithromycin, respectively.