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E6376

Sigma-Aldrich

Erythromycin

potency: ≥850 μg per mg

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

Quality Level

biological source

Streptomyces erythreus

form

powder

potency

≥850 μg per mg

color

white

solubility

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

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

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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Related Categories

General description

Chemical structure: macrolide

Packaging

25, 100 g in poly bottle

Application

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.

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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...
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)...
David J Serisier et al.
JAMA, 309(12), 1260-1267 (2013-03-28)
Macrolide antibiotics such as erythromycin may improve clinical outcomes in non-cystic fibrosis (CF) bronchiectasis, although associated risks of macrolide resistance are poorly defined. To evaluate the clinical efficacy and antimicrobial resistance cost of low-dose erythromycin given for 12 months to...

Related Content

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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