1242000

Erythromycin

United States Pharmacopeia (USP) Reference Standard

• Empirical Formula (Hill Notation): C₃₇H₆₇NO₁₃
• CAS Number: 114-07-8
• Molecular Weight: 733.93
• Beilstein: 75279
• MDL number: MFCD00084654
• UNSPSC Code: 41116107
• PubChem Substance ID: 329749382
• NACRES: NA.24

Properties

• grade: pharmaceutical primary standard
• API family: erythromycin
• manufacturer/tradename: USP
• application(s): pharmaceutical (small molecule)
• format: neat
• storage temp.: −20°C
• 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

Description

General description

Erythromycin is an antibiotic produced by growth of certain strains of Streptomyces erythreus. Erythromycin, a bacteriostatic antibiotic, inhibits the growth of bacteria instead of killing them directly. It functions as a cytochrome P-450 inhibitor and is primarily excreted through bile. Erythromycin consists primarily of erythromycin A (C₃₇H₆₇NO₁₃). The sum of the percentages of erythromycin A, erythromycin B, and erythromycin C is NLT 85.0% and NMT 100.5%, calculated on the anhydrous basis. Erythromycin demonstrates activity against both gram-positive and gram-negative bacteria, as well as other organisms. 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.

Erythromycin USP reference standard is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including MSDS and any product information leaflets, have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Erythromycin USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:

• Erythromycin Stearate
• Erythromycin Ethylsuccinate
• Erythromycin Lactobionate for Injection
• Erythromycin Ointment
• Erythromycin Pledgets
• Erythromycin Injection

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.

Other Notes

This product is part of the USP Biologics program.

Legal Information

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable