Teicoplanin A2-1
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| Category | Antibiotics |
| Catalog number | BBF-03494 |
| CAS | 91032-34-7 |
| Molecular Weight | 1877.64 |
| Molecular Formula | C88H95Cl2N9O33 |
| Purity | >98% by HPLC |
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Description
Teicoplanin A2-1 is a glycopeptide antibiotic produced by Actinoplanes teichomyceticus nov. sp. (ATTCC 31121). Activity against gram-positive bacteria.
Specification
| Synonyms | 34-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-22,31-dichloro-7-demethyl-64-O-demethyl-19-deoxy-56-O-[2-deoxy-2-[[(4Z)-1-oxo-4-decenyl]amino]-β-D-glucopyranosyl]-42-O-α-D-mannopyranosyl-ristomycin A aglycone |
| Storage | Store at -20°C |
| IUPAC Name | 2-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-amino-5,15-dichloro-64-[3-[[(Z)-dec-4-enoyl]amino]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid |
| Canonical SMILES | CCCCCC=CCCC(=O)NC1C(C(C(OC1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)C(C6C(=O)NC(C7=C(C(=CC(=C7)O)OC8C(C(C(C(O8)CO)O)O)O)C9=C(C=CC(=C9)C(C(=O)N6)NC(=O)C4NC(=O)C1C2=CC(=CC(=C2)OC2=C(C=CC(=C2)C(C(=O)NC(CC2=CC(=C(O3)C=C2)Cl)C(=O)N1)N)O)O)O)C(=O)O)OC1C(C(C(C(O1)CO)O)O)NC(=O)C)Cl)CO)O)O |
| InChI | InChI=1S/C88H95Cl2N9O33/c1-3-4-5-6-7-8-9-10-60(108)94-68-74(113)71(110)58(32-101)129-87(68)132-78-55-26-40-27-56(78)126-52-18-14-38(24-47(52)90)77(131-86-67(92-34(2)103)73(112)70(109)57(31-100)128-86)69-84(121)98-66(85(122)123)45-29-42(105)30-54(127-88-76(115)75(114)72(111)59(33-102)130-88)61(45)44-23-37(13-15-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-21-41(104)28-43(22-39)124-53-25-36(12-16-50(53)107)62(91)80(117)93-48(79(116)95-64)20-35-11-17-51(125-55)46(89)19-35/h7-8,11-19,21-30,48,57-59,62-77,86-88,100-102,104-107,109-115H,3-6,9-10,20,31-33,91H2,1-2H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)/b8-7- |
| InChI Key | YMWQIYMUNZBOOV-FPLPWBNLSA-N |
| Source | Actinoplanes sp. |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Density | 1.7±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Teicoplanin metabolism in humans
L F Zerilli, M Zanol, A Borghi, M Borgonovi, P Ferrari, A Bernareggi, K Vékey, L Cavenaghi Antimicrob Agents Chemother . 1992 Aug;36(8):1744-9. doi: 10.1128/AAC.36.8.1744.
Teicoplanin, a lipoglycopeptide antibiotic, consists of five major components (A2-1 through A2-5), one hydrolysis component (A3-1), and four minor components (RS-1 through RS-4). All the major components contain an N-acyl-beta-D-glucosamine, but they differ in the lengths and branchings of their acyl-aliphatic chains. Previous studies with radiolabeled teicoplanin in rats and humans have shown that the drug is eliminated by the renal route and that metabolic transformation is very minor, about 5%. A possible metabolic transformation of teicoplanin into A3-1 was also suggested. In the present study in humans, two metabolites (metabolites 1 and 2; 2 to 3% of total teicoplanin) were isolated after intravenous administration of radiolabeled teicoplanin. After purification, their structures were determined by fast atom bombardment mass spectroscopy and 1H nuclear magnetic resonance spectroscopy on the basis of the well-known correlations established in this field, and they were found to be new teicoplaninlike molecules, bearing 8-hydroxydecanoic and 9-hydroxydecanoic acyl moieties. This metabolic transformation is likely due to hydroxylation in the omega-2 and omega-1 positions for metabolites 1 and 2, respectively, of the C-10 linear side chain of component A2-3. This might explain the low extent of metabolism of teicoplanin if we consider that only component A2-3 has a linear chain that is susceptible to such oxidation.
2. Quantification of teicoplanin in plasma by LC-MS with online sample clean-up and comparison with QMS assay
Daniel M Mueller, Arnold von Eckardstein, Lanja Saleh Clin Chem Lab Med . 2014 Jun;52(6):879-87. doi: 10.1515/cclm-2013-0974.
Background:Teicoplanin is a glycopeptide antibiotic used for the treatment of infections caused by Gram-positive bacteria. There is a good correlation between trough levels and clinical outcome, therefore therapeutic drug monitoring is recommended. Here we present a liquid chromatography-mass spectrometry (LC-MS) method with online extraction based on turbulent flow chromatography for the quantification of the five main components of teicoplanin, A2-1, A2-2, A2-3, A2-4, and A2-5.Methods:After online extraction, analytical chromatography was performed on a Hypersil Gold C8 column under acidic conditions. As mass spectrometer, a Q Exactive hybrid instrument was used. Samples were prepared by adding internal standard and subsequent centrifugation. Patient samples (n=125) that had previously been analyzed using a commercially available immunoassay (QMS teicoplanin) were re-analyzed by LC-MS.Results:The imprecision was <6.9%, inaccuracy between 99.6% and 109%, for both, within- and between-day analysis. The method was shown to be free of matrix effects in the relevant time ranges and was compared to a commercially available immunoassay, QMS® teicoplanin from Thermo Fisher Scientific. The LC-MS assay produced comparable results to the QMS assay, the correlation coefficient was 0.856 (95% confidence interval 0.800-0.896). LC-MS yielded lower concentrations than the immunoassay as could be demonstrated by the bias of -1.16 mg/L (95% confidence interval -1.90-0.43 mg/L) in the Bland-Altman analysis.Conclusions:This specific, automated, LC-MS assay for teicoplanin is suitable for therapeutic drug monitoring.
3. Improved quantitative determination of total and unbound concentrations of six teicoplanin components in human plasma by high performance liquid chromatography
Toshimi Kimura, Kazuhiko Hanada, Hiroyasu Ogata, Akiko Kobayashi, Yumi Okamori Biol Pharm Bull . 2005 Oct;28(10):2023-5. doi: 10.1248/bpb.28.2023.
Total and unbound concentrations of six teicoplanin components in human plasma were determined by high-performance liquid chromatography with a coextractive cleanup technique. Unbound concentrations of teicoplanin components were estimated after ultrafiltration of plasma. For determination of each component in plasma, plasma was deproteinized with acetonitrile and the supernatant was shaken for 60 s with chloroform under acidic conditions. The recoveries of A3-1, A2-1, A2-2, A2-3, A2-4 and A2-5 were greater than 88%. The within-day and between-day coefficients of variation were 1.3-8.8% and 2.8-11.9%, respectively. The limits of detection in ultrafiltered plasma for each component were 0.82, 2.87, 4.23, 3.36, 7.33 and 4.93 nM, respectively. A good correlation was observed between the FPIA and HPLC methods when total concentrations of each teicoplanin component in patient plasma were determined. The analytical methods established in this study are suitable for determining the total and unbound concentrations of six components of teicoplanin in human plasma and for studying the pharmacokinetics of teicoplanin components in patients.
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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 ╳
