Doxycycline EP Impurity B
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| Category | Others |
| Catalog number | BBF-03960 |
| CAS | 914-00-1 |
| Molecular Weight | 442.42 |
| Molecular Formula | C22H22N2O8 |
| Purity | >98% by HPLC |
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Description
Meclocycline is a semi-synthetic tetracycline prepared by dehydrating the 6-hydroxyl group of oxytetracycline. It has a wide range of antibacterial and antiprotozoal activities. Meclocycline is an impurity of Doxycycline, which is a semisynthetic, broad-spectrum tetracycline antibiotic used in the treatment of infections caused by bacteria and certain parasites.
Specification
| Related CAS | 3963-95-9 (monohydrochloride) 54559-08-9 (hydrobromide) 98897-96-2 (x-hydrochloride) 352465-26-0 (nitrate salt) 39180-63-7 (sulfate salt) |
| Synonyms | Doxycycline hyclate EP impurity B; Doxycycline monohydrate EP impurity B; 6-Methyleneoxytetracycline; Metacycline; Rondomycin; 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S,4aR,5S,5aR,12aS)-; (4S,4aR,5S,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide; 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, [4S-(4α,4aα,5α,5aα,12aα)]-; 6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline; 6-Deoxy-6-methylene-6-demethyl-5-hydroxytetracycline; 6-Methylene-5-hydroxytetracycline; 6-Methyleneoxytetracycline; Bialatan; GS 2876; Oxytetracycline, 6-methylene-; Rondomycin; Tri-methacycline |
| Storage | Store at 2-8°C |
| IUPAC Name | (4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide |
| Canonical SMILES | O=C(N)C=1C(=O)C2(O)C(O)=C3C(=O)C=4C(O)=CC=CC4C(=C)C3C(O)C2C(C1O)N(C)C |
| InChI | InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1 |
| InChI Key | MHIGBKBJSQVXNH-IWVLMIASSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Yellow to Orange Solid |
| Application | Antibiotics, Tetracycline |
| Boiling Point | 806.5±65.0°C at 760 mmHg |
| Melting Point | >150°C (dec.) |
| Density | 1.66±0.1 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol (Slightly), Water (Slightly) |
Reference Reading
1.Production of monoclonal antibody against doxycycline for immunoassay of seven tetracyclines in bovine muscle and milk.
Gao F1, Zhao GX, Zhang HC, Wang P, Wang JP. J Environ Sci Health B. 2013;48(2):92-100. doi: 10.1080/03601234.2013.726856.
The objective of this study was to produce a generic monoclonal antibody for multi-determination of the residues of tetracycline drugs in bovine muscle and milk. Two new immunogens of doxycycline were prepared that were used to produce the monoclonal antibodies. Results showed the obtained antibodies simultaneously recognized seven tetracycline drugs (doxycycline, tetracycline, chlortetracycline, oxytetracycline, minocycline, methacycline, demeclocycline). The obtained antibodies and three coating antigens were arranged into six combinations to optimize the reagents combination. After comparison of the performances of these combinations, a heterologous indirect competitive ELISA was then used to determine the seven tetracyclines in bovine muscle and milk. The crossreactivities to the seven analytes were in the range of 47%-102% and the limits of detection were in the range of 1.5-6.9 ng/mL depending on the compound. The recoveries of the seven drugs from fortified blank samples were in the range of 75.
2.pH-dependent spectroscopy of tetracycline and its analogs.
Mojica ER1, Nguyen E, Rozov M, Bright FV. J Fluoresc. 2014 Jul;24(4):1183-98. doi: 10.1007/s10895-014-1399-7. Epub 2014 May 9.
Tetracyclines (TCs), broad spectrum antibiotics widely used in the prevention and treatment of infectious diseases, are amphoteric molecules containing several ionizable functional groups that exist predominantly as zwitterions at a given pH value. TCs are reported to undergo a wide variety of reactions at different pH values i.e. TCs form to anhydrotetracyclines at low pH, 4-epitetracyclines at pH 3-5 and isotetracyclines at high pH values. The pH-dependent absorbance and emission properties of tetracycline and its 10 analogs (4-epitetracycline, doxycyline, oxytetracycline, chlortetracycline, 4-epichlortetracycline, isochlortetracycline, methacycline, rolitetracycline, minocycline, and demeclocycline) were investigated and reported in this paper. The main focus of the study was on the pH dependent transformation of epichlortetracycline, chlortetracycline and isotetracycline at basic pH. Absorption, emission and time resolved spectroscopy were used to determine the behavior of the three TC derivatives at this condition.
3.Antibiotics in the coastal environment of the Hailing Bay region, South China Sea: Spatial distribution, source analysis and ecological risks.
Chen H1, Liu S2, Xu XR3, Zhou GJ2, Liu SS4, Yue WZ2, Sun KF2, Ying GG4. Mar Pollut Bull. 2015 Jun 15;95(1):365-73. doi: 10.1016/j.marpolbul.2015.04.025. Epub 2015 Apr 22.
In this study, the occurrence and spatial distribution of 38 antibiotics in surface water and sediment samples of the Hailing Bay region, South China Sea, were investigated. Twenty-one, 16 and 15 of 38 antibiotics were detected with the concentrations ranging from <0.08 (clarithromycin) to 15,163ng/L (oxytetracycline), 2.12 (methacycline) to 1318ng/L (erythromycin-H2O), <1.95 (ciprofloxacin) to 184ng/g (chlortetracycline) in the seawater, discharged effluent and sediment samples, respectively. The concentrations of antibiotics in the water phase were correlated positively with chemical oxygen demand and nitrate. The source analysis indicated that untreated domestic sewage was the primary source of antibiotics in the study region. Fluoroquinolones showed strong sorption capacity onto sediments due to their high pseudo-partitioning coefficients. Risk assessment indicated that oxytetracycline, norfloxacin and erythromycin-H2O posed high risks to aquatic organisms.
4.High-performance liquid chromatography using pressurized liquid extraction for the determination of seven tetracyclines in egg, fish and shrimp.
Liu Y1, Yang H, Yang S, Hu Q, Cheng H, Liu H, Qiu Y. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Feb 15;917-918:11-7. doi: 10.1016/j.jchromb.2012.12.036. Epub 2013 Jan 9.
A simple and especially rapid method, pressurized liquid extraction, has been developed and applied to the quantitative determination of oxytetracycline, tetracycline, chlortetracycline, minocycline, methacycline, demeclocycline and doxycycline in egg, fish and shrimp. The procedure consisted of a trichloracetic acid/methanol extraction conducted at elevated temperature (60°C) and pressure (65bar), without further clean-up, the extraction solution was concentrated and finally for high-performance liquid chromatography analysis. The limits of detection were 5.0-10.0μg/kg and the limits of quantification were 10.0-15.0μg/kg for tetracyclines in egg, fish and shrimp using UV detection. The analytical limits CCα and CCβ were also calculated. The recoveries of tetracyclines spiked at levels of 15-300μg/kg, averaged 75.6-103.5% with the relative standard deviation values less than 11%. The optimized procedure has been successfully applied to real samples in our laboratories.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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