Erythromycylamine
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| Category | Antibiotics |
| Catalog number | BBF-04636 |
| CAS | 26116-56-3 |
| Molecular Weight | 734.96 |
| Molecular Formula | C37H70N2O12 |
| Purity | >95% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04636 | 50 mg | $439 | In stock |
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Add to cartDescription
Erythromycylamine is a macrolide antibiotic and an active metabolite of dirithromycin. It is active against a variety of bacteria, including strains of S. pyogenes, S. pneumoniae, L. monocytogenes and B. pertussis. A derivative of Erythromycin.
Specification
| Synonyms | (9S)-9-Amino-9-deoxoerythromycin; (9S)-9-Deoxy-9-aminoerythromycin A; (9S)-Erythromycylamine A; 9(S)-Erythromycylamine; BRL 42852ER; LY 024410; Dirithromycin EP Impurity A |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-10-amino-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one |
| Canonical SMILES | CCC1C(C(C(C(C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)N)C)O)(C)O |
| InChI | InChI=1S/C37H70N2O12/c1-14-25-37(10,45)30(41)20(4)27(38)18(2)16-35(8,44)32(51-34-28(40)24(39(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-32,34,40-42,44-45H,14-17,38H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1 |
| InChI Key | XCLJRCAJSCMIND-JCTYMORFSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 810.3±65.0°C (Predicted) |
| Melting Point | 123-127°C |
| Density | 1.19±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Water, Chloroform |
Reference Reading
1. Quantitative determination of erythromycylamine in human plasma by liquid chromatography-mass spectrometry and its application in a bioequivalence study of dirithromycin
Yun-Qing Liu, Qi-Yuan Chen, Ben-Mei Chen, Shao-Gang Liu, Fu-Liang Deng, Ping Zhou J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Mar 15;864(1-2):1-8. doi: 10.1016/j.jchromb.2007.12.021. Epub 2008 Jan 4.
A sensitive, rapid liquid chromatographic-electrospray ionization mass spectrometric method for determination of erythromycylamine in human plasma was developed and validated. Erythromycylamine in plasma (0.2 mL) was extracted with ethyl acetate, the organic phase was transferred to another clear 1.5 mL Eppendorf tube and evaporated to dryness under gentle nitrogen stream at 45 degrees C, and the residue was dissolved in 100 microL of mobile phase. The samples were separated using a Thermo Hypersil HyPURITY C18 reversed-phase column (150 mm x 2.1 mm I.D., 5 microm). A mobile phase containing 10 mM of ammonium acetate (pH = 6.4)-acetonitrile-methanol (50:10:40, v/v/v) was used isocratically eluting at a flow rate of 0.2 mL/min. Erythromycylamine and its internal standard (IS), midecamycin, were measured by electrospray ion source in positive selective ion monitoring mode. The method demonstrated that good linearity ranged from 4.5 to 720 ng/mL with r = 0.9997. The limit of quantification for erythromycylamine in plasma was 4.5 ng/mL with good accuracy and precision. The mean extraction recovery of the method was higher than 75.1% and 72.7% for erythromycylamine and IS, respectively. The intra-day and inter-day precision ranged from 5.2% to 6.4% and 5.6-9.3% (relative standard deviation, RSD), respectively. The established method has been successfully applied to a bioequivalence study of two dirithromycin formulations for 18 healthy volunteers.
2. Identifying unknown antibiotics with persistent and bioaccumulative properties and ecological risk in river water in Beijing, China
Qingwei Bu, Hongmei Cao, Qingshan Li, Handan Zhang, Weiwei Jiang, Gang Yu Environ Sci Pollut Res Int. 2021 Mar;28(11):13515-13523. doi: 10.1007/s11356-020-11611-4. Epub 2020 Nov 13.
The goal of this study was to identify antibiotics with potential risk in river water of the megacity Beijing, China. This was accomplished by using a tiered approach that combined hazard (phase I) and monitoring-based risk (phase II) assessment. Ninety-five candidate antibiotics were screened and 31 was identified as hazardous during phase I assessment. Of these hazardous antibiotics, 29 were identified as persistent and 7 were identified as bioaccumulative antibiotics. Fluoroquinolones, macrolides, sulfonamides, and aminoglycosides account for over 80% of these hazardous antibiotics. During phase II, four antibiotics (erythromycylamine, cefotaxime, ampicillin, and fusidic acid) that were not previously reported were detected in the surface water sampled from four major rivers in Beijing, with concentrations ranging from not detected to approximately 300 ng/L. The ecological risk assessment showed that erythromycylamine, cefotaxime, and ampicillin posed low to high levels of risk to the aquatic organisms. To summarize, erythromycylamine, cefotaxime, and ampicillin were identified as priority antibiotics in rivers in Beijing, China. Our results demonstrated the necessity of conducting monitoring-based verification process in identification of priority antibiotics in a specific region.
3. Quantitative analysis of erythromycylamine in human plasma by liquid chromatography-tandem mass spectrometry and its application in a bioequivalence study of dirithromycin enteric-coated tablets with a special focus on the fragmentation pattern and carryover effect
Hua-Lin Cai, Feng Wang, Huan-De Li, Wen-Xing Peng, Rong-Hua Zhu, Yang Deng, Pei Jiang, Miao Yan, Si-Miao Hu, Su-Yun Lei, Chang Chen J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Feb 1;947-948:156-63. doi: 10.1016/j.jchromb.2013.12.019. Epub 2013 Dec 27.
A liquid chromatography-tandem mass spectrometry method was developed and validated for the quantification of erythromycylamine, which is the predominant active metabolite of dirithromycin in human plasma. After solid-phase extraction, the analyte and internal standard (IS) were separated by using an isocratic mobile phase consisting of 20 mM ammonium acetate (pH 3.9, adjusted with formic acid)-acetonitrile (75:25, v/v) on a Phenyl-Hexyl column (150 × 2.1 mm, 3 μm) and then analyzed in positive ion mode under electrospray ionization. Azithromycin was selected as the IS because it has the most similar mass spectrometric and chromatographic behaviors to the analyte. The respective multiple reaction monitoring (MRM) transitions, m/z 368.5>83.2 for erythromycylamine and m/z 375.4>115.2 for IS were chosen to achieve high sensitivity and selectivity in determination. A more acidic mobile phase (pH 3.9) than those of previous reports and a special needle wash (ethylene glycol-acetonitrile-water, 50:30:20, v/v/v, adjusted to pH 3.9 using formic acid) were used to eliminate the carryover effects of the two macrolides. The method exhibited a linear dynamic range of 0.5-440.0 ng/mL for erythromycylamine in human plasma (r=0.9999). The lower limit of quantification (LLOQ) and limit of detection (LOD) were 0.5 and 0.05 ng/mL, respectively. The mean extraction recoveries were higher than 94.0% for the analyte and IS. The intra- and inter-day precisions ranged from 1.4 to 5.4% and from 1.6 to 4.0%, respectively. The accuracy varied between 91.2 and 101.2%. The established method was successfully applied to analyze the human plasma samples from 24 healthy subjects in a bioequivalence study of two dirithromycin enteric-coated formulations.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
