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E5389

Sigma-Aldrich

Erythromycin

BioReagent, suitable for cell culture

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Synonym(s):
E-Mycin, Erythrocin
Empirical Formula (Hill Notation):
C37H67NO13
CAS Number:
114-07-8
Molecular Weight:
733.93
Beilstein:
75279
EC Number:
204-040-1
MDL number:
MFCD00084654
PubChem Substance ID:
24894612
NACRES:
NA.76

product line

BioReagent

form

powder

potency

≥850 μg per mg

technique(s)

cell culture | mammalian: suitable

impurities

≤0.1 EU/mg endotoxin

color

white

mp

133 °C

solubility

2 M HCl: 50 mg/mL (Stock solutions should be stored at 2-8 °C. Stable at 37 °C for 3 days.)
ethanol: soluble (Stock solutions should be stored at 2-8 °C. Stable at 37 °C for 3 days.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

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)

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General description

Chemical structure: macrolide
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.

Application

Erythromycin has been used:
  • as a supplement for nutrient broth medium for culturing green fluorescent protein (GFP)- expressing E. coli
  • as a model drug to determine small intestinal (SMI) microtissue viability using the MTT assay{254
  • as an antibiotic to study the treatment strategies of chronic infections

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Acoustofluidic bacteria separation
Li S, et al.
Journal of Micromechanics and Microengineering, 27(1), 015031-015031 (2016)
Drug-driven phenotypic convergence supports rational treatment strategies of chronic infections
Imamovic L, et al.
Cell, 172(1-2), 121-134 (2018)
Anna C Shore et al.
Antimicrobial agents and chemotherapy, 54(12), 4978-4984 (2010-10-06)
The staphylococcal cfr gene mediates resistance to phenicols, lincosamides, oxazolidinones, pleuromutilins, and streptogramin A, a phenotype that has been termed PhLOPS(A). The cfr gene has mainly been associated with coagulase-negative staphylococcal isolates from animals, and only a few cfr-positive methicillin-resistant
Elisabet I Nielsen et al.
Antimicrobial agents and chemotherapy, 51(1), 128-136 (2006-10-25)
Dosing of antibacterial agents is generally based on point estimates of the effect, even though bacteria exposed to antibiotics show complex kinetic behaviors. The use of the whole time course of the observed effects would be more advantageous. The aim
Christoph Czarnetzki et al.
JAMA surgery, 150(8), 730-737 (2015-06-18)
Patients undergoing emergency procedures under general anesthesia have impaired gastric emptying and are at high risk for aspiration of gastric contents. Erythromycin has strong gastric prokinetic properties. To evaluate the efficacy of erythromycin lactobionate in gastric emptying in patients undergoing
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Articles

Inhibition of Protein Synthesis by Antibiotics

Protein synthesis is a complex, multi-step process involving many enzymes as well as conformational alignment. However, the majority of antibiotics that block bacterial protein synthesis interfere with the processes at the 30S subunit or 50S subunit of the 70S bacterial ribosome.

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