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E8630

Sigma-Aldrich

Erythromycin estolate

Synonym(s):

Erythromycin 2′-propionate dodecyl sulfate

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About This Item

Linear Formula:
C40H71NO14 · C12H26SO4
CAS Number:
Molecular Weight:
1056.39
EC Number:
MDL number:
UNSPSC Code:
51101500
PubChem Substance ID:

form

solid

color

white

solubility

chloroform: 4.0 mL, clear, colorless (200 mg + 4.0 mL Chloroform)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

protein synthesis | interferes

SMILES string

CCCCCCCCCCCCOS(O)(=O)=O.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(C)[C@@H](O)[C@@]1(C)O

InChI

1S/C37H67NO13.C12H26O4S/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;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;2-12H2,1H3,(H,13,14,15)/t18-,19+,20?,21+,22-,23-,24-,25?,26-,28+,29+,30+,31-,32-,34-,35-,36+,37+;/m0./s1

InChI key

SKDGGFHGLZBNBC-CAHOBLCESA-N

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General description

Chemical structure: macrolide

Application

Erythoromycin estolate is used to study hepatic cytochrome P-450 induction and inactivation via cytochrome-metabolite complex formation[1] and Giardia intestinalis inefections[2]. It is used to study antibiotic cytotoxicity in cultured human liver cell lines[3].

Biochem/physiol Actions

Erythromycin inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site) by binding to the 50s subunit of the bacterial 70s rRNA complex.
Erythromycin inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site).

pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3


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P F Boreham et al.
The Journal of antimicrobial chemotherapy, 16(5), 589-595 (1985-11-01)
The activities of 11 5-nitroimidazole compounds have been compared against Giardia intestinalis in vitro using a 3H-thymidine incorporation assay. All the compounds were at least equipotent to, or more active than metronidazole with the exception of panidazole. Satranidazole, ronidazole and
M Viluksela et al.
The Journal of antimicrobial chemotherapy, 38(3), 465-473 (1996-09-01)
Cytotoxicity of erythromycin base, erythromycin estolate, erythromycin-11,12-cyclic carbonate, roxithromycin, clarithromycin and azithromycin was compared in cultured human non-malignant Chang liver cells using reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide and cellular protein concentration as end points of toxicity. Erythromycin estolate was the
D E Amacher et al.
Antimicrobial agents and chemotherapy, 35(6), 1186-1190 (1991-06-01)
Erythromycin and some other macrolide antibiotics can first induce a cytochrome P-450 isozyme similar to the one induced in rats by pregnenolone-16 alpha-carbonitrile and then inhibit it by forming a stable cytochrome P-450-metabolite complex. The purpose of this study was
Cholestatic hepatitis caused by esters of erythromycin and oleandomycin. 1962.
F I Gilbert
Hawaii medical journal, 54(6), 603-605 (1995-06-11)
Pidaran Murugan et al.
Journal of basic and clinical physiology and pharmacology, 16(1), 1-15 (2005-09-29)
Erythromycin estolate (EME), a potent macrolide antibiotic, generates free radicals, but their role in the development of liver toxicity is not yet well understood. The present study was carried out to investigate the effect of the antioxidant drug tetrahydrocurcumin (a

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