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45674

Sigma-Aldrich

Erythromycin

tested according to Ph. Eur.

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Synonym(s):
Erythromycinum
Empirical Formula (Hill Notation):
C37H67NO13
CAS Number:
Molecular Weight:
733.93
Beilstein:
75279
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.76

Agency

EPA 1694
USP/NF
tested according to Ph. Eur.

Quality Level

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

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

application(s)

environmental

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

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1 of 4

This Item
E0774PHR1039E1300000
Erythromycin tested according to Ph. Eur.

Sigma-Aldrich

45674

Erythromycin

Erythromycin meets USP testing specifications

Sigma-Aldrich

E0774

Erythromycin

Erythromycin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1039

Erythromycin

Erythromycin for microbiological assay, European Pharmacopoeia (EP) Reference Standard

E1300000

Erythromycin

color

white to faint yellow

color

-

color

-

color

-

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

solubility

ethanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

-

solubility

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

-

application(s)

environmental

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

-

mode of action

-

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.

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

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T Peeters et al.
The American journal of physiology, 257(3 Pt 1), G470-G474 (1989-09-01)
Erythromycin A (EMA) is a potent stimulator of gastrointestinal motor activity. In vitro studies suggest that it mimics motilin, a peptide that stimulates motor activity in human and in rabbit via smooth muscle receptors. We have compared the in vitro
Nicole Wolter et al.
Antimicrobial agents and chemotherapy, 51(3), 1092-1095 (2007-01-11)
A rare clinical isolate of Streptococcus pneumoniae, highly resistant to telithromycin, contained erm(B) with a truncated leader peptide and a mutant ribosomal protein L4. By transformation of susceptible strains, this study shows that high-level telithromycin resistance is conferred by erm(B)
Ying Ying Chan et al.
Antimicrobial agents and chemotherapy, 51(2), 623-630 (2006-12-06)
The gram-negative soil bacillus Burkholderia pseudomallei is the causative agent of melioidosis, a severe and potentially fatal septicemic disease that is endemic to Southeast Asia and northern Australia. Its intrinsic resistance to many antibiotics is attributed mainly to the presence
Leena Keurulainen et al.
Journal of medicinal chemistry, 53(21), 7664-7674 (2010-10-12)
Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other
Markus Hilleringmann et al.
The EMBO journal, 28(24), 3921-3930 (2009-11-28)
Although the pili of Gram-positive bacteria are putative virulence factors, little is known about their structure. Here we describe the molecular architecture of pilus-1 of Streptococcus pneumoniae, which is a major cause of morbidity and mortality worldwide. One major (RrgB)

Articles

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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