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Purity: ≥98%
| Targets |
Macrolide antibiotic
Erythromycin estolate, like erythromycin, inhibits bacterial protein synthesis by reversibly binding to the 50S subunit of bacterial ribosomes near the 'P' or donor site, blocking the binding of tRNA to the donor site. This prevents the translocation step of protein synthesis, leading to inhibition of bacterial growth. The estolate prodrug form improves oral absorption and bioavailability. |
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| ln Vitro |
Azithromycin, an azalide analog of erythromycin was assayed for its in vitro activity against multidrug-resistant Plasmodium falciparum K1 strain by measuring the 3H-hypoxanthine incorporation. Azithromycin caused inhibitory effects on the parasite growth with IC50 and IC90 values of 8.4+/-1.2 microM and 26.0+/-0.9 microM, respectively. Erythromycin inhibited growth of P. falciparum with IC50 and IC90 values of 58.2+/-7.7 microM and 104.0+/-10.8 microM, respectively. The activity of antimalarial drugs in combination with azithromycin or erythromycin against P. falciparum K1 were compared. Combinations of chloroquine with azithromycin or erythromycin showed synergistic effects against parasite growth in vitro. Combinations of quinine-azithromycin and quinine-erythromycin showed potentiation. Additive effects were observed in mefloquine-azithromycin and mefloquine-erythromycin combinations. Similar results were also produced by pyronaridine in combination with azithromycin or erythromycin. However, artesunate-azithromycin and artesunate-erythromycin combinations had antagonistic effects. The in vitro data suggest that azithromycin and erythromycin will have clinical utility in combination with chloroquine and quinine. The worldwide spread of chloroquine-resistant P. falciparum might inhibit the ability to treat malaria patients with chloroquine-azithromycin and chloroquine-erythromycin in areas of drug-resistant. The best drug combinations against multidrug-resistant P. falciparum are quinine-azithromycin and quinine-erythromycin [2].
In vitro, erythromycin estolate demonstrates broad-spectrum antibacterial activity against various Gram-positive and Gram-negative bacteria. Its activity is assessed using standard broth microdilution or agar diffusion methods to determine minimum inhibitory concentrations (MIC) against target bacterial strains. The compound's inhibitory effect on bile acid transport has also been noted. |
| ln Vivo |
Erythromycin estolate (EE), a macrolide antibiotic, has caused hepatotoxicity both in human and experimental animals. The objective of this study was to integrate general toxicology, transcriptomics, and metabonomics approaches to determine the mechanisms of EE-induced liver injury. Histopathological examinations unveiled dose-dependent hydropicdegenerationof hepatocytes after EE administration. Further biochemical analysis of treated rats confirmed that cholestasis and oxidative stress were induced by EE treatments. Microarray analysis of the livers from EE-treated rats showed that differentially expressed genes were enriched in the ABC transporters, cell cycle, and p53 signaling pathways. Metabonomics analysis revealed that EE exposure could lead to disturbances in energy metabolism, amino acid metabolism, lipid metabolism, and nucleotide metabolism, which may be attributable to EE toxicological effects on the liver through oxidative stress. 5-Oxoproline may be used as a biomarker of EE-induced liver injury. More importantly, the integrated analysis of transcriptomics and metabonomics datasets demonstrated that the induction of ABC transporters pathway severed as an anti-cholestatic adaptive mechanism in EE-induced cholestasis. In addition, EE-induced liver injury was also related to alteration in glycogen and sucrose metabolism, arachidonic acid metabolism, and linoleic acid metabolism pathways [4].
In vivo, erythromycin estolate is used for the treatment of respiratory tract infections, skin and soft tissue infections, otitis media, and certain sexually transmitted diseases. It is prescribed as a first-line or alternative therapy for these indications. The prodrug's improved oral bioavailability supports convenient oral dosing. |
| Enzyme Assay |
Non-cellular enzyme assays for erythromycin estolate are not standard, as it is an antibiotic that acts on bacterial ribosomes. Its binding to bacterial ribosomes can be assessed using cell-free translation assays with bacterial lysates (e.g., E. coli S30 extract) and a reporter mRNA (e.g., luciferase). The inhibition of protein synthesis is measured by quantifying the reduction in reporter activity. Its effects on bile acid transport can be assessed using membrane vesicle preparations.
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| Cell Assay |
In vitro cellular assays for erythromycin estolate involve treating bacterial cultures with the compound and assessing growth inhibition. Cultures of Gram-positive and Gram-negative bacteria are incubated with varying concentrations of erythromycin estolate, and bacterial growth is measured by optical density or colony counting. The minimum inhibitory concentration (MIC) is determined from dose-response curves. The compound's bactericidal or bacteriostatic activity is assessed using time-kill assays.
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| Animal Protocol |
In vivo animal experiments with erythromycin estolate are conducted in animal models of bacterial infection. Mice or rats are infected with pathogenic bacteria (e.g., S. aureus or S. pneumoniae) and treated with erythromycin estolate via oral administration. The compound's efficacy is assessed by measuring survival rates, bacterial load in tissues, and resolution of clinical signs of infection. Pharmacokinetic studies characterize absorption and distribution of the prodrug and active erythromycin.
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| ADME/Pharmacokinetics |
Erythromycin estolate has a molecular weight of 1056.40 and a molecular formula of C₅₂H₉₇NO₁₈S. It is a solid powder with a purity of ≥98%. The compound is typically stored at room temperature in a dry, dark place. It is soluble in organic solvents such as DMSO. The compound is stable under recommended storage conditions.
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| Toxicity/Toxicokinetics |
Erythromycin estolate is generally well-tolerated, but it has been associated with a higher risk of liver injury compared to other erythromycin salts. It may cause cholestatic hepatitis, jaundice, and paucity of bile ducts. It is contraindicated in patients with pre-existing liver disease. Standard safety precautions should be followed when handling the compound.
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| References |
[1].Gribble MJ, et al. Erythromycin. Med Clin North Am. 1982 Jan;66(1):79-89. [3]. Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. [4]. Integrated systems toxicology approaches identified the possible involvement of ABC transporters pathway in erythromycin estolate-induced liver injury in rat. Food Chem Toxicol. 2014 Mar;65:343-55. |
| Additional Infomation |
Erythromycin ester is an aminoglycoside sulfate and a derivative of erythromycin. It is an enzyme inhibitor. It contains erythromycin A 2'-propionate. Erythromycin ester is lauryl sulfate of propionyl erythromycin, a broad-spectrum topical macrolide antibiotic with antibacterial activity. Erythromycin ester diffuses across the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This inhibits bacterial protein synthesis. The action of erythromycin ester may be bacteriostatic or bactericidal, depending on the drug concentration at the site of infection and the sensitivity of the associated microorganism. A macrolide antibiotic produced by Streptomyces erythromycinus. It is the lauryl sulfate of erythromycin propionate. This erythromycin salt primarily functions as a bacteriostatic agent. In susceptible bacteria, it inhibits protein synthesis by binding to the 50S ribosomal subunit. This binding process inhibits peptidyl transferase activity and interferes with amino acid translocation during translation and protein assembly. See also: erythromycin (containing the active moiety); erythromycin ester; sulfamethoxazole acetyl (component).
Erythromycin estolate (CAS 3521-62-8) is a semi-synthetic derivative of the macrolide antibiotic erythromycin, designed to improve stability and oral bioavailability. It inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit. Erythromycin estolate is used for the treatment of respiratory, skin, and soft tissue infections. The compound is available from various commercial suppliers for research applications. |
| Molecular Formula |
C52H97NO18S
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|---|---|
| Molecular Weight |
1056.3875
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| Exact Mass |
999.616
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| Elemental Analysis |
C, 59.12; H, 9.26; N, 1.33; O, 27.26; S, 3.03
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| CAS # |
3521-62-8
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| Related CAS # |
114-07-8 (free); 3521-62-8 (estolate); 16667-03-1 (glutamate); 30010-41-4 (aspartate); 7704-67-8 (thiocyante); 1264-62-6 (Ethylsuccinate); 914076-30-5 (ethyl carbonate); 55224-05-0 (cyclocarbonate); 33396-29-1 (Erythromycin A enol ether); 59319-72-1 (Erythromycin A dihydrate) |
| PubChem CID |
441371
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| Appearance |
White to off-white solid powder
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| Density |
1.0053 (rough estimate)
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| Boiling Point |
827.7ºC at 760 mmHg
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| Melting Point |
135-140ºC dec.
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| Flash Point |
454.4ºC
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| Index of Refraction |
1.6550 (estimate)
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| Source |
Streptomyces erythrus
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| LogP |
7.554
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
19
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| Rotatable Bond Count |
22
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| Heavy Atom Count |
72
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| Complexity |
1550
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| Defined Atom Stereocenter Count |
18
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| SMILES |
S(=O)(=O)(O[H])OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H].O([C@@]1([H])[C@@]([H])([C@]([H])(C([H])([H])[C@@]([H])(C([H])([H])[H])O1)N(C([H])([H])[H])C([H])([H])[H])OC(C([H])([H])C([H])([H])[H])=O)[C@@]1([H])[C@@](C([H])([H])[H])(C([H])([H])[C@@]([H])(C([H])([H])[H])C([C@]([H])(C([H])([H])[H])[C@]([H])([C@@](C([H])([H])[H])([C@@]([H])(C([H])([H])C([H])([H])[H])OC([C@]([H])(C([H])([H])[H])[C@]([H])([C@]1([H])C([H])([H])[H])O[C@@]1([H])C([H])([H])[C@](C([H])([H])[H])([C@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])OC([H])([H])[H])=O)O[H])O[H])=O)O[H]
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| InChi Key |
AWMFUEJKWXESNL-JZBHMOKNSA-N
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| InChi Code |
InChI=1S/C40H71NO14.C12H26O4S/c1-15-27-40(11,48)33(44)22(5)30(43)20(3)18-38(9,47)35(55-37-32(53-28(42)16-2)26(41(12)13)17-21(4)50-37)23(6)31(24(7)36(46)52-27)54-29-19-39(10,49-14)34(45)25(8)51-291-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h20-27,29,31-35,37,44-45,47-48H,15-19H2,1-14H32-12H2,1H3,(H,13,14,15)/t20-,21-,22+,23+,24-,25+,26+,27-,29+,31+,32-,33-,34+,35-,37+,38-,39-,40-/m1./s1
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| Chemical Name |
(2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl
propionate dodecyl sulfate
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| Synonyms |
NSC 263364 NSC-263364 NSC263364 Ilosone Lauromicina
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| HS Tariff Code |
2934.99.03.00
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~94.66 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (1.97 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (1.97 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (1.97 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.9466 mL | 4.7331 mL | 9.4662 mL | |
| 5 mM | 0.1893 mL | 0.9466 mL | 1.8932 mL | |
| 10 mM | 0.0947 mL | 0.4733 mL | 0.9466 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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