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Purity: ≥98%
Erythromycin Ethylsuccinate 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; Antiviral; HIV-1
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|---|---|
| ln Vitro |
Macrophages (MPhis) are a major source of HIV-1 especially in patients with tuberculosis. There are MPhis that are permissive and those that restrict HIV-1. Regulation of hematopoietic cell kinase (Hck) activity and selective expression of CCAAT enhancer binding protein beta (C/EBPbeta) isoforms greatly contribute to determine distinct susceptibility of MPhis to HIV-1. Resistance is attributable to reduced expression of Hck and augmented expression of an inhibitory small isoform of C/EBPbeta. Derivatives of erythromycin A (EMA) EM201 and EM703 inhibit the replication of HIV-1 in tissue MPhis, at posttranscriptional and translational levels. We demonstrate that EM201 and EM703 convert tissue MPhis from HIV-1 susceptible to HIV-1 resistant through down-regulation of Hck and induction of small isoforms of C/EBPbeta. These drugs inhibit p38MAPK activation which is expressed only in susceptible tissue MPhis. Activated CD4(+)T cells stimulate the viral replication in HIV-1 resistant MPhis through down-regulation of small isoforms of C/EBPbeta via activation of ERK1/2. EM201 and EM703 can inhibit the MAPK activation and inhibit the burst of viral replication produced when CD4(+)T cells and MPhis interact. These EM derivatives may be highly beneficial for repression of residual HIV-1 in the lymphoreticular system of HIV-1-infected patients and offer great promise for the creation of new anti-HIV drugs for the future treatment of AIDS patients [4].
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| ln Vivo |
In Sweden there are several reports of mares developing acute colitis while their foals were being treated orally for Rhodococcus equi pneumonia with the combination of erythromycin and rifampicin. In this study 6 adult horses were given low oral dosages of these antibiotics, singly or in combination. Within 3 days post administration of erythromycin, in one case in combination with rifampicin, 2 horses developed severe colitis (one fatal). Clostridium difficile was isolated from one of the horses, whereas no specific pathogens were isolated from the other. Both horses had typical changes in blood parameters seen in acute colitis. Clostridium difficile was also isolated from the faeces of a third horse given an even lower dosage of erythromycin in combination with rifampicin. This horse developed very mild clinical symptoms and recovered spontaneously. In the fourth horse given erythromycin only, very high numbers of Clostridium perfringens were isolated. The horses given rifampicin only did not develop any clinical symptoms and there were no major changes in their faecal flora. In conclusion, it has been demonstrated that low dosages of erythromycin ethylsuccinate can induce severe colitis in horses associated with major changes of the intestinal microflora. Clostridium difficile has been demonstrated as a potential aetiological agent in antibiotic-induced acute colitis [5].
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| Enzyme Assay |
HIV-1 Strain and Infection. M-tropic HIV-1 strain, HIV-1BaL, was collected from culture supernatant of the HIV-1 strain-infected M-MΦs as a viral resource. Mo-derived MΦs were incubated for 2 h at 37°C with 100 pg/ml p24 antigen of DNase-treated viral supernatant (p24, the 50% tissue culture infective dose (TCID50) and multiplicity of infection (MOI) are 50 ng/ml, ∼3,000 and 0.05, respectively) and then cultured in RPMI MEDIUM 1640 containing 10% FCS and CSF. If necessary, the viral inoculum was pretreated with 100 μM AZT for 2 h at 4°C. Fresh culture medium containing CSF was added every 3–4 d (20% of the volume). Heat-inactivated virus (1 h, 56°C) was used as negative control. Viral production was assayed by sequential measurement of p24 antigen in supernatants by an ELISA using a combination of two antibodies; anti-gag-p24 monoclonal antibody (Nu24) and peroxidase-labeled 10B5, or the RETRO-TEK HIV-1 p24 antigen ELISA kit for high-affinity detection of low levels of p24 antigen[4].
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| Cell Assay |
Coculture of HIV-1 Infected GM-MΦs with the Activated CD4+T Cells. CD4+ T cells were positively isolated from CD14− PBMCs using a MACS with anti-CD4 mAb coated microbeads. The selected population was >93% positive for CD3 and CD4. Activated CD4+ T cells were prepared by stimulation with PHA and cultured with IL-2 (30 unit/ml). GM-MΦs were incubated for 2 h at 37°C with 100 pg/ml p24 antigen of DNase-treated viral supernatant, washed twice, and then cocultured with the activated CD4+ T cells in the presence of IL-2 [4].
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| References |
[1]. Erythromycin. Med Clin North Am. 1982 Jan;66(1):79-89. [4]. Erythromycin derivatives inhibit HIV-1 replication in macrophages through modulation of MAPK activity to induce small isoforms of C/EBPbeta. Proc Natl Acad Sci U S A. 2008 Aug 26;105(34):12509-14.[5]. The association of erythromycin ethylsuccinate with acute colitis in horses in Sweden. Equine Vet J. 1997 Jul;29(4):314-8. |
| Molecular Formula |
C43H75NO16
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|---|---|
| Molecular Weight |
862.0527
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| Exact Mass |
861.51
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| Elemental Analysis |
C, 59.91; H, 8.77; N, 1.62; O, 29.69
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| CAS # |
1264-62-6
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| Related CAS # |
Erythromycin;114-07-8;Erythromycin ethylsuccinate-13C,d3
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| Appearance |
White to off-white solid powder
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| Source |
Saccharopolyspora erythraea
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| LogP |
4.10
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| tPSA |
26.28
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| SMILES |
CCOC(CCC(O[C@H]1[C@@H](O[C@@H](C[C@@H]1N(C)C)C)O[C@@H]2[C@H]([C@@H]([C@H](C(O[C@@H]([C@@](O)([C@@H]([C@H](C([C@@H](C[C@]2(O)C)C)=O)C)O)C)CC)=O)C)O[C@H]3C[C@@](OC)([C@H]([C@@H](O3)C)O)C)C)=O)=O
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| InChi Key |
NSYZCCDSJNWWJL-YXOIYICCSA-N
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| InChi Code |
InChI=1S/C43H75NO16/c1-15-29-43(11,52)36(48)24(5)33(47)22(3)20-41(9,51)38(25(6)34(26(7)39(50)57-29)59-32-21-42(10,53-14)37(49)27(8)56-32)60-40-35(28(44(12)13)19-23(4)55-40)58-31(46)18-17-30(45)54-16-2/h22-29,32,34-38,40,48-49,51-52H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,32+,34+,35-,36-,37+,38-,40+,41-,42-,43-/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
ethyl succinate
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| Synonyms |
Erythromycin ethylsuccinate; E-Mycin E; E.E.S; Wyamycin; Wyamycin E;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| 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 : ≥ 50 mg/mL (~58.00 mM)
Ethanol :≥ 33.33 mg/mL (~38.66 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.90 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 25.0 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: ≥ 2.5 mg/mL (2.90 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1600 mL | 5.8001 mL | 11.6003 mL | |
| 5 mM | 0.2320 mL | 1.1600 mL | 2.3201 mL | |
| 10 mM | 0.1160 mL | 0.5800 mL | 1.1600 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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