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Merck
CN

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:
3521-62-8
Molecular Weight:
1056.39
EC Number:
222-532-4
MDL number:
MFCD00084691
UNSPSC Code:
51101500
PubChem Substance ID:
24894679

Key Documents

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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 and Giardia intestinalis inefections. It is used to study antibiotic cytotoxicity in cultured human liver cell lines.

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
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H317,H334

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
082K1186
080K1594
051K1554
124F02851
111K1095

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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
S Venkateswaran et al.
Journal of ethnopharmacology, 57(3), 161-167 (1997-08-01)
Livex, a compound herbal formulation, was investigated for its possible hepatoprotective effect in Wistar rats against erythromycin estolate induced toxicity. Oral administration of Livex significantly prevented the occurrence of erythromycin estolate induced hepatic damage. The increased level of serum enzymes
H Scholz et al.
European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology, 17(7), 470-478 (1998-10-09)
Erythromycin is frequently prescribed in Germany for acute otitis media, but well-designed clinical trials under present epidemiological conditions are lacking. Therefore, a double-blind, randomized, multicenter trial was performed to compare the clinical efficacy and safety of erythromycin estolate versus amoxicillin
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