Apramycin (Nebramycin II)
(Synonyms: 安普霉素) 目录号 : GC32288
Apramycin(NebramycinII)是氨基糖苷类抗生素，用于兽医。
Cas No.:37321-09-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Apramycin(Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. IC50 value:Target: Apramycin stands out among aminoglycosides for its mechanism of action which is based on blocking translocation and its ability to bind also to the eukaryotic decoding site despite differences in key residues required for apramycin recognition by the bacterial target. The drug binds in the deep groove of the RNA which forms a continuously stacked helix comprising non-canonical C.A and G.A base pairs and a bulged-out adenine. The binding mode of apramycin at the human decoding-site RNA is distinct from aminoglycoside recognition of the bacterial target, suggesting a molecular basis for the actions of apramycin in eukaryotes and bacteria.
[1]. Apramycin, From Wikipedia
| Cas No. | 37321-09-8 | SDF | |
| 别名 | 安普霉素 | ||
| Canonical SMILES | O[C@H]1[C@](O[C@H](O[C@@]([C@H](C[C@H]2N)N)([H])[C@@H]([C@H]2O)O)[C@H](N)C3)([H])[C@@]3([H])O[C@H](O[C@@]([C@@H]([C@@H](O)[C@@H]4N)O)([H])O[C@@H]4CO)[C@H]1NC | ||
| 分子式 | C21H41N5O11 | 分子量 | 539.58 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°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 | 1.8533 mL | 9.2665 mL | 18.5329 mL |
| 5 mM | 0.3707 mL | 1.8533 mL | 3.7066 mL |
| 10 mM | 0.1853 mL | 0.9266 mL | 1.8533 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。
High affinity of copper(II) towards amoxicillin, Apramycin and ristomycin. Effect of these complexes on the catalytic activity of HDV ribozyme
J Inorg Biochem 2013 Jul;124:26-34.PMID:23583885DOI:10.1016/j.jinorgbio.2013.03.002.
Three representatives of the distinct antibiotics groups: amoxicillin, Apramycin and ristomycin A were studied regarding their impact on hepatitis D virus (HDV) ribozyme both in the metal-free form and complexed with copper(II) ions. Hence the Cu(II)-ristomycin A complex has been characterized by means of NMR, EPR, CD and UV-visible spectroscopic techniques and its binding pattern has been compared with the coordination modes estimated previously for Cu(II)-amoxicillin and Cu(II)-apramycin complexes. It has thus been found that all three antibiotics bind the Cu(II) ion in a very similar manner, engaging two nitrogen and two oxygen donors into coordination with the square planar symmetry in physiological conditions. All three tested antibiotics were able to inhibit the HDV ribozyme catalysis. However, in the presence of the complexes, the catalytic reactions were almost completely inhibited. It was important therefore to check whether the complexes used in lower concentrations could inhibit the HDV ribozyme catalytic activity, thus creating opportunities for their practical application. It turned out that the complexes used in the concentrations of 50渭M influenced the catalysis much less effectively comparing to the 200 micromolar concentration. The kobs values were lower than those observed in the control reaction, in the absence of potential inhibitors: 2-fold for amoxicillin, ristomycin A and 3.3-fold for Apramycin, respectively.
Population pharmacokinetics of Apramycin from first-in-human plasma and urine data to support prediction of efficacious dose
J Antimicrob Chemother 2022 Sep 30;77(10):2718-2728.PMID:35849148DOI:10.1093/jac/dkac225.
Background: Apramycin is under development for human use as EBL-1003, a crystalline free base of Apramycin, in face of increasing incidence of multidrug-resistant bacteria. Both toxicity and cross-resistance, commonly seen for other aminoglycosides, appear relatively low owing to its distinct chemical structure. Objectives: To perform a population pharmacokinetic (PPK) analysis and predict an efficacious dose based on data from a first-in-human Phase I trial. Methods: The drug was administered intravenously over 30 min in five ascending-dose groups ranging from 0.3 to 30 mg/kg. Plasma and urine samples were collected from 30 healthy volunteers. PPK model development was performed stepwise and the final model was used for PTA analysis. Results: A mammillary four-compartment PPK model, with linear elimination and a renal fractional excretion of 90%, described the data. Apramycin clearance was proportional to the absolute estimated glomerular filtration rate (eGFR). All fixed effect parameters were allometrically scaled to total body weight (TBW). Clearance and steady-state volume of distribution were estimated to 5.5 L/h and 16 L, respectively, for a typical individual with absolute eGFR of 124 mL/min and TBW of 70 kg. PTA analyses demonstrated that the anticipated efficacious dose (30 mg/kg daily, 30 min intravenous infusion) reaches a probability of 96.4% for a free AUC/MIC target of 40, given an MIC of 8 mg/L, in a virtual Phase II patient population with an absolute eGFR extrapolated to 80 mL/min. Conclusions: The results support further Phase II clinical trials with Apramycin at an anticipated efficacious dose of 30 mg/kg once daily.
Detection and characterization of aparmycin-resistant Escherichia coli from humans in Korea
Microb Drug Resist 2011 Dec;17(4):563-6.PMID:21905874DOI:10.1089/mdr.2011.0052.
To investigate Apramycin resistance in humans in Korea, a total of 138 human Escherichia coli strains confirmed as gentamicin-resistant were collected from Korean Culture Collection Antimicrobial-Resistant Microbes. Apramycin resistance (minimum inhibitory concentrations 鈮?,024 渭g/ml) was observed in 16 (11.6%) of the 138 gentamicin-resistant E. coli (GREC) strains. Among the seven different kinds of aminoglycoside resistance genes tested, only four kinds were detected in the apramycin-resistant GREC strains: aac (3)-II, aac (3)-III, aac (3)-IV, and armA. The aac (3)-IV gene was found in all apramycin-resistant GREC strains, whereas aac(3)-II, aac(3)-III, and armA genes were detected in 8 (50.0%), 6 (37.5%), and 1 (6.3%) GREC strains resistant to Apramycin, respectively. Of 16 apramycin-resistant GREC strains, transfer of Apramycin resistance was observed in seven (43.8%), and co-transfer of resistance to other antimicrobials along with Apramycin resistance was also found in four strains (25.0%) by broth mating. The results of this study suggest that more prudential use of Apramycin in animals is needed.
Structural features and oxidative stress towards plasmid DNA of Apramycin copper complex
Dalton Trans 2009 Feb 21;(7):1123-30.PMID:19322482DOI:10.1039/b815046j.
The interaction of Apramycin with copper at different pH values was investigated by potentiometric titrations and EPR, UV-vis and CD spectroscopic techniques. The Cu(II)-apramycin complex prevailing at pH 6.5 was further characterized by NMR spectroscopy. Metal-proton distances derived from paramagnetic relaxation enhancements were used as restraints in a conformational search procedure in order to define the structure of the complex. Longitudinal relaxation rates were measured with the IR-COSY pulse sequence, thus solving the problems due to signal overlap. At pH 6.5 Apramycin binds copper(II) with a 2 : 1 stoichiometry, through the vicinal hydroxyl and deprotonated amino groups of ring III. Plasmid DNA electrophoresis showed that the Cu(II)-apramycin complex is more active than free Cu(II) in generating strand breakages. Interestingly, this complex in the presence of ascorbic acid damages DNA with a higher yield than in the presence of H(2)O(2).
Apramycin and gentamicin resistances in indicator and clinical Escherichia coli isolates from farm animals in Korea
Foodborne Pathog Dis 2011 Jan;8(1):119-23.PMID:21214385DOI:10.1089/fpd.2010.0641.
A total of 1921 Escherichia coli isolated from healthy animals (501 from cattle, 832 from pigs, and 588 from chickens) and 237 isolates from diseased pigs were tested to determine the prevalence of Apramycin and gentamicin resistance in Korea during 2004-2007. Apramycin/gentamicin resistances observed in healthy cattle, pigs, and chicken were 0.2%/0.6%, 11.2%/13.6%, and 0.5%/18.2%, respectively. Gentamicin/Apramycin resistance was much higher in E. coli isolated from diseased pigs (71/237, 30.0%) than in those from healthy pigs (93/832, 11.2%). The aminoglycoside resistance gene content of all apramycin-gentamicin-resistant E. coli isolates (n= 164) was determined by polymerase chain reaction. Of seven different types of aminoglycoside resistance genes tested, five kinds were detected in the 164 isolates: aac(3)-IV, aac(3)-II, aac(3)-III, ant(2'')-I, and armA. All apramycin-resistant E. coli contained the aac(3)-IV gene. About half of the resistant isolates carried only the aac(3)-IV gene and the other half carried other genes in addition to aac(3)-IV. The results of the present study suggest that humans are at risk of gentamicin resistance from Apramycin use in animals.