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Key Documents

1242000

USP

Erythromycin

United States Pharmacopeia (USP) Reference Standard

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About This Item

Formule empirique (notation de Hill):
C37H67NO13
Numéro CAS:
Poids moléculaire :
733.93
Numéro Beilstein :
75279
Numéro MDL:
Code UNSPSC :
41116107
ID de substance PubChem :
Nomenclature NACRES :
NA.24

Qualité

pharmaceutical primary standard

Famille d'API

erythromycin

Fabricant/nom de marque

USP

Application(s)

pharmaceutical (small molecule)

Format

neat

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

ULGZDMOVFRHVEP-RWJQBGPGSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Attention

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

Notes préparatoires

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.

Autres remarques

This product is part of the USP Biologics program.

Informations légales

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.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Marina Mingoia et al.
Antimicrobial agents and chemotherapy, 58(10), 5886-5893 (2014-07-30)
The linkage between the macrolide efflux gene mef(I) and the chloramphenicol inactivation gene catQ was first described in Streptococcus pneumoniae (strain Spn529), where the two genes are located in a module designated IQ element. Subsequently, two different defective IQ elements
Eugene Ng et al.
The Cochrane database of systematic reviews, (3)(3), CD001815-CD001815 (2008-07-23)
Functional immaturity of gastrointestinal motility predisposes preterm infants to feeding intolerance. Erythromycin is a motilin agonist that exerts its prokinetic effect by stimulating propagative contractile activity in the interdigestive phase. To evaluate the efficacy of erythromycin in the prevention and
Hanne Jensen et al.
Microbiology (Reading, England), 160(Pt 4), 671-681 (2014-01-30)
Lactobacillus reuteri, a symbiotic inhabitant of the gastrointestinal tract in humans and animals, is marketed as a probiotic. The ability to adhere to intestinal epithelial cells and mucus is an interesting property with regard to probiotic features such as colonization
J A Washington et al.
Mayo Clinic proceedings, 60(4), 271-278 (1985-04-01)
Erythromycin, first introduced for clinical use 30 years ago, was found to be effective for the treatment of gram-positive bacterial infections. Emergence of resistance and the advent of penicillinase-resistant penicillins limited the use of erythromycin for serious staphylococcal infections; however
Catherine V Hawkyard et al.
The Journal of antimicrobial chemotherapy, 59(3), 347-358 (2007-02-10)
Erythromycin A, the first macrolide, was introduced in the 1950s and after years of clinical experience it still remains a commonly relied upon antibiotic. In the past, pharmacodynamic characteristics of macrolides beyond antimicrobial action such as anti-inflammatory and immune-modulating properties

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