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Purity: ≥98%
Erythromycin estolate is a potent and broad-spectrum antibiotic belonging to a group of drugs called macrolide antibiotics, it is produced by actinomycete Streptomyces erythreus and is an inhibitor of protein translation and mammalian mRNA splicing. It acts by binding to bacterial 50S ribosomal subunits and inhibits RNA-dependent protein synthesis by blockage of transpeptidation and/or translocation reactions, without affecting synthesis of nucleic acid, thus inhibiting growth of gram negative and gram positiove bacteria. Erythromycin is used to treat certain infections caused by bacteria, such as infections of the respiratory tract, including bronchitis, pneumonia, Legionnaires' disease (a type of lung infection), and pertussis (whooping cough; a serious infection that can cause severe coughing); diphtheria (a serious infection in the throat); sexually transmitted diseases (STD), including syphilis; and ear, intestine, gynecological, urinary tract, and skin infections.
| Targets |
Macrolide antibiotic
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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].
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| 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].
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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 estolate is an aminoglycoside sulfate salt and an erythromycin derivative. It has a role as an enzyme inhibitor. It contains an erythromycin A 2'-propanoate.
Erythromycin Estolate is the lauryl sulfate ester of propionyl erythromycin, a broad-spectrum, topical macrolide antibiotic with antibacterial activity. Erythromycin estolate diffuses through the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This prevents bacterial protein synthesis. Erythromycin estolate may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved. A macrolide antibiotic, produced by Streptomyces erythreus. It is the lauryl sulfate salt of the propionic ester of erythromycin. This erythromycin salt acts primarily as a bacteriostatic agent. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. See also: Erythromycin (has active moiety); Erythromycin estolate; sulfisoxazole acetyl (component of). |
| 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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