Erythromycin Ethylsuccinate

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Cat Number

API1264626

CAS Number

1264-62-6

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CAS Number

1264-62-6

EINECS

215-033-8

Storage

Room temperature

Synonyms

Erythromycin ethyl succinate;erythromycin,mono(ethylsuccinate);erythromycin,mono(ethylsuccinate)(ester)

Molecular Formula

C43H75NO16

Molecular Weight

862.1

Smiles

CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)OC(=O)CCC(=O)OCC)(C)O)C)C)O)(C)O

Appearance

White solid

Melting Point

219-224℃

Boiling Point

778.19℃

Relative Density

1.14

pKa

13.09

General Description

Erythromycin Ethylsuccinate is the ethylsuccinate ester prodrug of the macrolide antibiotic erythromycin. It provides improved gastric acid stability and bioavailability compared to erythromycin base.

Mechanism of Action

Erythromycin binds to the 50S ribosomal subunit, inhibiting peptidyl transferase and blocking peptide chain elongation during protein synthesis, producing bacteriostatic effects against susceptible organisms.

Application

Used in the treatment of respiratory tract and skin infections. Erythromycin Ethylsuccinate is indicated for upper and lower respiratory tract infections, skin infections, and atypical infections caused by Mycoplasma and Chlamydia.

The solubility of Erythromycin Ethylsuccinate in six organic solvents (tetrahydrofuran, acetone, acetonitrile, hexane, ethanol, 2-propanol) was measured at 288.15–323.15 K using gravimetry. Solubility increased with temperature (endothermic dissolution). Data were correlated with four models; modified Apelblat gave the best fit. Mixing thermodynamics from NRTL showed spontaneous dissolution. Hansen solubility parameters explained the observed order: hexane < acetonitrile < ethanol < 2-propanol < acetone < tetrahydrofuran.

Fig. 1 Experimental and correlated solubility of EES in different pure solvents. (Zhang X.; et al. 2017)

References

Zhang X, et al. Solubility and mixing thermodynamics properties of erythromycin ethylsuccinate in different organic solvents. Journal of Molecular Liquids, 2017, 237: 46-53.

Erythromycin ethylsuccinate was formulated into solid lipid nanoparticles using heating emulsification and homogenization methods to enhance its aqueous solubility. Formula 1 achieved an encapsulation efficiency of 85.688 percent with a particle size of 398.9 nm, polydispersity index of 0.3895, and zeta potential of -17.45 mV. The solubility of erythromycin ethylsuccinate in the solid lipid nanoparticle formulation was increased compared to the pure substance. Stability was determined by accelerated testing under extreme temperature and mechanical stress conditions, with pH decrease and particle precipitation serving as indicators of instability.

Fig. 2 Preparation of Erythromycin ethylsuccinate solid lipid nanoparticles. (Mardiyanto M.; et al. 2022)

References

Mardiyanto M, et al. Formulation and Evaluation of Solid Lipid Nanoparticles Loading Erythromycin Ethylsuccinate by Heating Emulsification and Homogenization Methods. Science and Technology Indonesia, 2022, 7(3): 320-326.

What advantage does the ethylsuccinate ester offer over erythromycin base?

The ethylsuccinate prodrug provides improved acid stability and oral bioavailability, reducing gastrointestinal degradation and enhancing systemic absorption.

What storage conditions are required?

Store at room temperature in a tightly sealed container, protected from light and moisture.

What purity grade is available?

It is supplied as a high-purity grade suitable for R&D and pharmaceutical manufacturing.

Can packaging and order quantities be customized?

Yes, both packaging formats and order quantities can be tailored to meet specific R&D and production needs.