Anhydroerythromycin A
(Synonyms: 脱水红霉素) 目录号 : GC40850
A degradation product of erythromycin
Cas No.:23893-13-2
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
Anhydroerythromycin A is a degradation product of the macrolide antibiotic erythromycin . It is formed via degradation of erythromycin in acidic aqueous solutions in vitro as well as in vivo. Anhydroerythromycin A is active against S. aureus and B. cereus in vitro (MICs = 12.5 and 6.25 μg/ml, respectively). It also inhibits steroid 6β-hydroxylase activity associated with the cytochrome P450 (CYP) isoform CYP3A in human liver microsomes.
| Cas No. | 23893-13-2 | SDF | |
| 别名 | 脱水红霉素 | ||
| Canonical SMILES | C[C@@H]1C[C@@]([C@H](O[C@@]2([H])[C@H](O)[C@@H](N(C)C)C[C@@H](C)O2)[C@@H](C)[C@H](O[C@@]3([H])C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@H]4C)(C)O[C@]51[C@H](C)[C@@H](O)[C@@](O5)(C)[C@@H](CC)OC4=O | ||
| 分子式 | C37H65NO12 | 分子量 | 715.9 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 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 | 1.3968 mL | 6.9842 mL | 13.9684 mL |
| 5 mM | 0.2794 mL | 1.3968 mL | 2.7937 mL |
| 10 mM | 0.1397 mL | 0.6984 mL | 1.3968 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。
Determination of the stereochemistry of Anhydroerythromycin A, the principal degradation product of the antibiotic erythromycin A
Org Biomol Chem 2006 Mar 21;4(6):1014-9.PMID:16525545DOI:10.1039/b518182h.
Anhydroerythromycin A arises from the acid-catalysed degradation of erythromycin A both in vitro and in vivo. It has negligible antibacterial activity, but inhibits drug oxidation in the liver, and is responsible for unwanted drug-drug interactions. Its structure has 18 chiral centres common with erythromycin A, but C-9 (the spiro carbon) is also chiral in anhydroerythromycin and its stereochemistry has not previously been reported; both 9R- and 9S-anhydroerythromycin A are plausible structures. An understanding of the chirality at C-9 was expected to throw light on the mechanism of acid-catalysed degradation of erythromycin A, a subject that has been debated in the literature over several decades. We now report a determination of the three-dimensional structure of Anhydroerythromycin A, including the stereochemistry at C-9, by NMR and molecular modelling. In parallel, the relative stereochemistry of Anhydroerythromycin A 2'-acetate was determined by X-ray crystallography. Both compounds were shown to have 9R stereochemistry, and Anhydroerythromycin A exhibited considerable conformational flexibility in solution.
A kinetic study on the degradation of erythromycin A in aqueous solution
Int J Pharm 2004 Mar 1;271(1-2):63-76.PMID:15129974DOI:10.1016/j.ijpharm.2003.10.023.
The pH is a critical factor determining the rate of the degradation of erythromycin A in aqueous solutions. However, the kinetics of the acid- and base-catalyzed degradation is still uncertain. This study used a sensitive coulometric detection method to determine concentrations of erythromycin A and its degradation products. To determine the buffer-independent rate constants, sodium acetate (0.05-0.2 M) and Tris-HCl (0.1-0.5 M) were used in a pH range of 3.5-5.5 and 7.0-9.0, respectively. In acidic conditions, Anhydroerythromycin A appeared to be produced directly through an internal dehydration of erythromycin A-6,9-hemiketal which simultaneously established an equilibrium with erythromycin A enol ether on the other hand. In weakly alkaline conditions, hydroxide ion appeared to catalyze the hydrolysis of the lactonyl ester bond of erythromycin A-6,9-hemiketal by the pseudo-first-order kinetics, and the C13 --> C11 translactonization and internal dehydration reactions subsequently occurred to form pseudoerythromycin A enol ether. We suggest here a predictive model for reasonable interpretation of the kinetics of erythromycin A degradation in aqueous solutions, in which the observed rate constant was expressed by the sum of the partial reaction rate constants for the acid- and base-catalyzed degradation of erythromycin A-6,9-hemiketal as a function of pH in a range of 3.0-10.0.
Mechanism for the degradation of erythromycin A and erythromycin A 2'-ethyl succinate in acidic aqueous solution
J Phys Chem A 2007 Oct 11;111(40):10098-104.PMID:17880049DOI:10.1021/jp073030y.
A major drawback of the antibiotic erythromycin A is its extreme acid sensitivity, leading to rapid inactivation in the stomach. The accepted model for degradation in aqueous acidic solution has erythromycin A in equilibrium with erythromycin A enol ether and degrading to Anhydroerythromycin A. We report a detailed kinetic study of the acidic degradation of erythromycin A and of erythromycin A 2'-ethyl succinate (the market-leading pediatric prodrug), investigating the reaction rates and degradation products via NMR. This reveals that the accepted mechanism is incorrect and that both the enol ether and the anhydride are in equilibrium with the parent erythromycin. By implication, both the anhydride and enol ether are antibacterially inactive reservoirs for the parent erythromycin. The actual degradation pathway is the slow loss of cladinose from erythromycin A (or erythromycin A 2'-ethyl succinate), which is reported here for the first time in a kinetic study. The kinetic analysis is based on global, nonlinear, simultaneous least-squares fitting of time course concentrations for all species across multiple datasets to integrated rate expressions, to provide robust estimates of the rate constants.
Development and validation of a multiclass method for the determination of antibiotic residues in honey using liquid chromatography-tandem mass spectrometry
Food Addit Contam Part A Chem Anal Control Expo Risk Assess 2017 Apr;34(4):582-597.PMID:27601204DOI:10.1080/19440049.2016.1232491.
A new, simple and fast method was developed for the determination of multi-class antibiotic residues in honey (sulfonamides, tetracyclines, macrolides, lincosamides and aminoglycosides). Separation and determination were carried out by LC-MS/MS. During sample preparation, various parameters affecting extraction efficiency were examined, including the type of solvent, pH, efficiencies of cleavage of N-glycosidic linkages by hydrochloric acid, ultrasonic extraction and its duration compared with shaking, along with dispersive SPE clean-up. Experiments with fortified samples demonstrated that 10 min of ultrasonic treatment with acidified methanol (HCl 2 M) followed by dispersive SPE clean-up with 50 mg PSA gave an effective sample preparation method for several classes of antibiotics in honey. Anhydroerythromycin A, erythromycin A enol ether and desmycosin were used as markers for the presence of erythromycin A and tylosin A in honey samples. The method was validated according to European Commission Decision (EC) No. 2002/657. The recoveries of analytes ranged from 85% to 111%. Repeatability and intra-laboratory reproducibility were < 20.6% and 26.8%, respectively. Decision limit (CCα) and detection capability (CCβ) ranged from 6 to 9 µg kg-1 and from 7 to 13 µg kg-1, respectively, except for streptomycin and neomycin, which showed slightly higher CCα at 25 µg kg-1 and CCβ at 34 µg kg-1. Finally, the method was applied to the honey test material 02270 through a FAPAS proficiency test (PT) for the determination of tetracyclines. PT results were obtained within a z-score range of ±2, proving that the validated method is suitable for routine analysis to ensure the quality of honey.
Design for the transfer of a validated liquid chromatography/tandem mass spectrometry analytical method for the determination of antimicrobial residues in honey from low-resolution to high-resolution mass spectrometry
Rapid Commun Mass Spectrom 2017 Jul 15;31(13):1103-1110.PMID:28488287DOI:10.1002/rcm.7899.
Rationale: This paper investigates the validity of the transfer of a liquid chromatography/tandem mass spectrometry (LC/MS/MS) method for the determination of veterinary medicinal products in honey and compares it with an LC/linear ion trap/Orbitrap mass spectrometry method. A descriptive statistical approach was used in order to assess whether such a transfer would succeed or fail. This approach is based on the simultaneous evaluation of the trueness and of the intermediate precision for each compound at a 95% interval of confidence of both analytical techniques. Methods: Two grams of honey were placed in a centrifuge tube and diluted with 2.5 mL of ultra-pure water and 2.5 mL of acidified methanol with hydrochloric acid at 2 mol.mL-1 . The extract was purified with 50 mg of primary secondary amine and then analyzed using LC/MS/MS in multiple reaction monitoring (MRM) mode and LC/orbitrap high-resolution mass spectrometry in full scan mode. Both analytical techniques were compared by using the descriptive statistical approach for the determination of antimicrobial residues in honey. Results: The transfer of the method showed that the Orbitrap system provides the same accurate analytical results compared with the LC/MS/MS method except for 4-epitetracycline, Anhydroerythromycin A, erythromycin A enol ether, and dihydrostreptomycin. Furthermore, the LC/LTQ-Orbitrap system is capable of successfully competing with the LC/MS/MS method by additional provision of high mass resolution and mass accuracy even though it shows less sensitivity compared with the LC/MS/MS instrument. CCα levels for most analytes were 1.3 times higher by LC/MS/MS than those observed by LC/LTQ-Orbitrap. The method was assessed in terms of relative bias through analysis of a reference material provided by FAPAS (Food Analysis Performance and Assessment Scheme) and also through the control of several contaminated honey samples from local Lebanese markets. Satisfactory relative bias was below 22% except for tetracycline found in one sample that showed a higher bias at 29%. Conclusions: The LC/LTQ-Orbitrap method offers adequate performance in comparison with previously validated method on a LC/MS/MS system resulting in acceptance of the transfer of the method from LC/MS/MS to LC/LTQ-Orbitrap. Copyright © 2017 John Wiley & Sons, Ltd.