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E7904

Sigma-Aldrich

Erythromycin

Biotechnology Performance Certified

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About This Item

Empirical Formula (Hill Notation):
C37H67NO13
CAS Number:
114-07-8
Molecular Weight:
733.93
Beilstein:
75279
EC Number:
204-040-1
MDL number:
MFCD00084654
UNSPSC Code:
51101500
PubChem Substance ID:
24894661

grade

Biotechnology Performance Certified

form

solid

impurities

endotoxin, tested

color

white

mp

133 °C

solubility

ethanol: soluble

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

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

13 - Non 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Vanessa G Allen et al.
Antimicrobial agents and chemotherapy, 55(2), 703-712 (2010-11-26)
Surveillance of gonococcal antimicrobial resistance and the molecular characterization of the mechanisms underlying these resistance phenotypes are essential in order to establish correct empirical therapies, as well as to describe the emergence of new mechanisms in local bacterial populations. To
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