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45674 Sigma-Aldrich

Erythromycin

tested according to Ph. Eur.

Synonym: Erythromycinum

  • CAS Number 114-07-8

  • Empirical Formula (Hill Notation) C37H67NO13

  • Molecular Weight 733.93

  •  Beilstein/REAXYS Number 75279

  •  EC Number 204-040-1

  •  MDL number MFCD00084654

  •  PubChem Substance ID 329756889

  •  NACRES NA.76

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Properties

Related Categories 1694 Pharmaceuticals & Personal Care Products, A - K, Additional Standards, Analytical Standards, Analytical/Chromatography,
Agency/Method   EPA 1694
  tested according to Ph. Eur.
Quality Level   200
form   solid
color   white to faint yellow
solubility   H2O: soluble 2 mg/mL
  acetone: freely soluble
  acetonitrile: freely soluble
  alcohol: soluble
  amyl acetate: moderately soluble
  chloroform: soluble
  diethyl ether: soluble
  ethyl acetate: freely soluble
Featured Industry   Environmental
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
storage temp.   room temp
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.

Packaging

25g

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
KF437500
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

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 wi...
BioFiles 2006, 1.4, 17.
Keywords: Antibiotics, Environmental, Peptide synthesis

Peer-Reviewed Papers
15

References

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