E0774

Erythromycin

meets USP testing specifications

• Synonym(s): Erythromycin A
• Empirical Formula (Hill Notation): C₃₇H₆₇NO₁₃
• CAS Number: 114-07-8
• Molecular Weight: 733.93
• Beilstein/REAXYS Number: 75279
• EC Number: 204-040-1
• MDL number: MFCD00084654
• UNSPSC Code: 51282304
• PubChem Substance ID: 24894374
• NACRES: NA.76

Properties

• agency: USP/NF; meets USP testing specifications
• Quality Level: 200
• form: solid
• optical activity: [α]/D -78 to --71°
• solubility: ethanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive bacteria
• application(s): pharmaceutical (small molecule)
• mode of action: protein synthesis | interferes
• SMILES string: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
• InChI: 1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChI key: ULGZDMOVFRHVEP-RWJQBGPGSA-N
• Gene Information: human ... ABCB1(5243) , CYP3A4(1576) , MLNR(2862) ; mouse ... Abcb1a(18671) , Abcb1b(18669)

Description

General description

Chemical structure: macrolide

Application

Erythromycin is an antibiotic produced by growth of certain strains of Streptomyces erythreus. This product is composed largely of erythromycin A with small amounts of erythromycins B and C and is recommended for concentration at 100 mg/L. Concentrations between 50 and 200 mg/L have also proven effective in controlling bacterial growth. Erythromycin has been used as a motilin receptor agonist, to block respiratory glycoconjugate secretion in human airways in vitro, and for selecting plasmid-cured and recombinant lactococcus lactis MG1363 strains.

Biochem/physiol Actions

Mode of Action: Erythromycin acts by inhibiting elongation at the transpeptidation step, specifically aminoacyl translocation from the A-site to P-site by binding to the 50s subunit of the bacterial 70s rRNA complex.

Antimicrobial Spectrum: This product acts against both gram-negative and gram-positive bacteria.

Caution

This product is stable in solution at 37°C for 3 days. Stock solutions should be stored at 2-8°C.

Preparation Note

This product is soluble in water at 2 mg/mL, with a 0.067% solution in water yielding a pH of 8.0-10.5. It is also soluble in ethanol at 50 mg/mL, yielding a clear, colorless to faint yellow solution. It is freely soluble in alcohol, acetone, chloroform, acetonitrile and ethyl acetate but forms salts with acids. All solutions should be protected from light.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable