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Erythromycin

Name: Erythromycin
Brand: SIAL

meets USP testing specifications

Synonym(s):

Erythromycin A

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About This Item

Empirical Formula (Hill Notation):

C₃₇H₆₇NO₁₃

CAS Number:

114-07-8

Molecular Weight:

733.93

UNSPSC Code:

51282304

NACRES:

NA.76

PubChem Substance ID:

24894374

EC Number:

204-040-1

Beilstein/REAXYS Number:

75279

MDL number:

MFCD00084654

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Properties

Quality Segment

200

agency

USP/NF, meets USP testing specifications

form

solid

optical activity

[α]/D -78 to --71°

solubility

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

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

application(s)

pharmaceutical (small molecule)

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)

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.

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.

Disclaimer

This product is stable in solution at 37°C for 3 days. Stock solutions should be stored at 2-8°C.

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1 of 1

This Item	45674	PHR1039	E1300000
Sigma-Aldrich E0774 Erythromycin	Sigma-Aldrich 45674 Erythromycin	Supelco PHR1039 Erythromycin	E1300000 Erythromycin
description meets USP testing specifications	description tested according to Ph. Eur.	description Pharmaceutical Secondary Standard; Certified Reference Material	description for microbiological assay, European Pharmacopoeia (EP) Reference Standard
antibiotic activity spectrum Gram-positive bacteria, Gram-negative bacteria	antibiotic activity spectrum Gram-positive bacteria, Gram-negative bacteria	antibiotic activity spectrum -	antibiotic activity spectrum -
mode of action protein synthesis \| interferes	mode of action protein synthesis \| interferes	mode of action -	mode of action -
Quality Level 200	Quality Level 200	Quality Level 300	Quality Level -
application(s) pharmaceutical (small molecule)	application(s) environmental	application(s) pharmaceutical (small molecule)	application(s) pharmaceutical (small molecule)
form solid	form solid	form -	form -
solubility ethanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow	solubility amyl acetate: moderately soluble, chloroform: soluble, ethyl acetate: freely soluble, diethyl ether: soluble, acetone: freely soluble, acetonitrile: freely soluble, alcohol: soluble, H₂O: soluble 2 mg/mL	solubility -	solubility -

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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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