Josamycin (EN-141)
(Synonyms: 交沙霉素; EN-141) 目录号 : GC32108
A macrolide antibiotic
Cas No.:16846-24-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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Kinase experiment: |
Josamycin is prepared in polymix buffer, containing 5 mM magnesium acetate, 5 mM ammonium chloride, 95 mM potassium chloride, 0.5 mM calcium chloride, 8 mM putrescine, 1 mM spermidine, 5 mM potassium phosphate, and 1 mM dithioerythritol. Josamycin at different concentrations (2, 3, 4, and 6 μM is added to preinitiated ribosomes to start the incubation. One volume of elongation mix is added to 1 volume of reaction mix at each incubation time, and after 10 s the reaction is quenched with formic acid. The association rates are estimated from the fraction of tri-peptide-forming ribosomes[1]. |
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Animal experiment: |
Rat: Tritium-labelled Josamycin (200 mg/kg) is orally administrated to rats. The blood and tissue levels are determined at 1 h and 3 h by bioassay[2].Mouse: Tritium-labelled Josamycin (200 mg/kg) is orally administrated to mice. The blood and tissue levels are determined at 1 h and 3 h by bioassay[2]. |
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References: [1]. Lovmar M, et al. Kinetics of macrolide action: the Josamycin and erythromycin cases. J Biol Chem. 2004 Dec 17;279(51):53506-15. |
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Josamycin is a macrolide antibiotic originally isolated from S. narbonensis.1 It is active against clinical isolates of the Gram-positive aerobic bacteria S. aureus, S. epidermidis, S. pneumoniae, S. pyogenes, and S. agalactiae (MIC50s = ≤0.39 ?g/ml for all), as well as the Gram-negative anaerobic bacteria Peptococcus, Peptostreptococcus, and Clostridium when used at concentrations of 6.25 ?g/ml.2 It increases survival in mouse models of systemic S. aureus, S. pyogenes, and S. pneumoniae infection with ED50 values of 206.8, 205, and 86.7 mg/kg, respectively.3
1.Osono, T., Oka, Y., Watanabe, S., et al.A new antibiotic, josamyicn. I. Isolation and physico-chemical characteristicsJ. Antibiot. (Tokyo)20(3)174-180(1967) 2.Reese, R.E., Betts, R.F., Goedde, L.W., et al.In vitro susceptibility of common clinical anaerobic and aerobic isolates against josamycinAntimicrob. Agents Chemother.10(2)253-257(1976) 3.Ono, T., Numata, K., Nagate, T., et al.In vitro and in vivo antibacterial activities of clarithromycinChemotherapy42(3)159-169(1996)
| Cas No. | 16846-24-5 | SDF | |
| 别名 | 交沙霉素; EN-141 | ||
| Canonical SMILES | O[C@H]1[C@](O[C@H](C)[C@@H](O[C@@](O[C@@H](C)[C@@H]2OC(CC(C)C)=O)([H])C[C@]2(O)C)[C@@H]1N(C)C)([H])O[C@@H]([C@H](C[C@H]([C@H](/C=C/C=C/C3)O)C)CC=O)[C@H]([C@](CC(O[C@@H]3C)=O)([H])OC(C)=O)OC | ||
| 分子式 | C42H69NO15 | 分子量 | 827.99 |
| 溶解度 | DMSO : ≥ 41.67 mg/mL (50.33 mM);Water : 2 mg/mL (2.42 mM; ultrasonic and adjust pH to 3 with water) | 储存条件 | Store at 4°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.2077 mL | 6.0387 mL | 12.0774 mL |
| 5 mM | 0.2415 mL | 1.2077 mL | 2.4155 mL |
| 10 mM | 0.1208 mL | 0.6039 mL | 1.2077 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
16-membered macrolide antibiotics: a review
Int J Antimicrob Agents2018 Mar;51(3):283-298.PMID:28668674DOI:10.1016/j.ijantimicag.2017.05.020.
The 16-membered macrolide antibiotics (e.g. tylosin A and Josamycin) are mainly used in veterinary medicine, and are much less studied than their 14- and 15-membered erythromycin-based cousins. Although these antibiotics have similar antibacterial profiles, with activity primarily against Gram-positive and a limited range of Gram-negative organisms, the 16-membered macrolides show some advantages. These include better gastrointestinal tolerance, lack of drug-drug interactions, and activity against certain resistant bacterial strains by extension of the peptide tunnel reach allowing additional interactions. In addition to antibacterial activity, the most famous representative of the class, tylosin A, as well as some derivatives of desmycosin (tylosin B), have shown antimalarial activity. Such activity has also been observed in the 14-membered macrolide antibiotics, azithromycin, solithromycin and clindamycin. This antimalarial activity provides the opportunity to investigate these drugs as cheap and effective antimalarials. This is an overview of the latest research on biosynthesis, structure, chemical properties and mode of action of 16-membered macrolides, with special emphasis on their most explored members: tylosin A and Josamycin.
Macrolides and gastrointestinal motility
J Antimicrob Chemother1988 Jul;22 Suppl B:201-6.PMID:3053572DOI:10.1093/jac/22.supplement_b.201.
Erythromycin was the first macrolide used clinically, and it is still the most widely prescribed in spite of reports of gastrointestinal side-effects. Erythromycin was given iv or orally to fasted and fed dogs with sensors implanted on the gastrointestinal tract for the measurement of motility. There was a large increase in stomach and upper small bowel contractile activity, accompanied by nausea and vomiting, while the distal small bowel appeared inhibited. Similar effects were seen in man. By contrast, two 16-membered macrolides, spiramycin and Josamycin, did not produce such side-effects when given either orally or intravenously to dogs.
Analysis of macrolide antibiotics
J Chromatogr A1998 Jul 3;812(1-2):255-86.PMID:9691324DOI:10.1016/s0021-9673(98)00276-3.
The following macrolide antibiotics have been covered in this review: erythromycin and its related substances, azithromycin, clarithromycin, dirithromycin, roxithromycin, flurithromycin, Josamycin, rokitamycin, kitasamycin, mycinamycin, mirosamycin, oleandomycin, rosaramicin, spiramycin and tylosin. The application of various thin-layer chromatography, paper chromatography, gas chromatography, high-performance liquid chromatography and capillary zone electrophoresis procedures for their analysis are described. These techniques have been applied to the separation and quantitative analysis of the macrolides in fermentation media, purity assessment of raw materials, assay of pharmaceutical dosage forms and the measurement of clinically useful macrolide antibiotics in biological samples such as blood, plasma, serum, urine and tissues. Data relating to the chromatographic behaviour of some macrolide antibiotics as well as the various detection methods used, such as bioautography, UV spectrophotometry, fluorometry, electrochemical detection, chemiluminescence and mass spectrometry techniques are also included.
Study on a terahertz biosensor based on graphene-metamaterial
Spectrochim Acta A Mol Biomol Spectrosc2022 Nov 5;280:121527.PMID:35753099DOI:10.1016/j.saa.2022.121527.
The interaction between the terahertz wave propagating in free space and the sample is weak, which leads to the weak signal of the sample, which cannot meet the detection needs of trace samples. In order to meet the detection of trace samples, a kind of metamaterial absorber (the basic unit of the absorber is composed of gold-high resistance silicon-aluminum three-layer structure) is designed, and the monolayer graphene is transferred on the surface of the metamaterial absorber to construct the graphene-metamaterial absorber heterostructure. The transmission spectrum of the resonant cavity is simulated and measured by terahertz time domain spectroscopy system, and the obvious resonance frequency shift is observed. The results show that the graphene-metamaterial absorber heterostructure can detect Josamycin antibiotic solution with concentration of 0.02 mg/L (the mass of Josamycin is 0.2 ng). Compared with using the same structure metamaterial absorber to detect Josamycin antibiotics, the sensitivity is increased by an order of magnitude. Using graphene-metamaterial heterostructure to detect the relative change of heterostructure reflectivity caused by Josamycin antibiotics can reach 40%. The research in this paper provides a new technical means for accurate and rapid detection in terahertz band.
[The pharmacokinetics of Josamycin]
Arzneimittelforschung1985;35(3):639-43.PMID:4039591doi
Determination of the distribution coefficients in vitro demonstrates that Josamycin (Wilprafen) is at least 15 times more lipophilic than erythromycin. On the other hand the distribution coefficients of penicillin G and of amoxicillin be in the hydrophilic range. The serum protein binding of Josamycin is 15%, which is markedly less than with the other macrolides. These in vitro experiments show that small structural differences can alter the physicochemical and biological behaviour of an antibiotic, even when the molecules are closely related. A cross-over experiment with 12 volunteers and multiple application of 1 g of Josamycin base or 1.175 g of erythromycin ethyl succinate showed that both macrolides are rapidly absorbed and reach their maximum within the first hour. In 21 patients the concentration of Josamycin in lung tissue was 2 to 3 times that in the blood. The highest concentration of Josamycin reached was 3.68 micrograms/g lung tissue (mean of 12 patients) and this was found for the group of patients from whom the tissue samples had been taken 2-3 h after the last administration of the drug. Lower mean concentrations of erythromycin were found in the serum and lung tissue of a similar group of 31 patients. The results indicate that the new macrolide antibiotic Josamycin accumulates well in lung tissue and that the concentrations necessary for the treatment of infections (minimal inhibitory concentrations [MIC]) are rapidly reached also in the tissue.