N-Desmethyl Clarithromycin
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| Category | Others |
| Catalog number | BBF-04429 |
| CAS | 101666-68-6 |
| Molecular Weight | 733.93 |
| Molecular Formula | C37H67NO13 |
| Purity | >95% |
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Description
A metabolite of the macrolide antibiotic, Clarithromycin.
Specification
| Synonyms | N-Demethyl-6-O-methylerythromycin; 3''-N-Demethylclarithromycin; N-Demethylclarithromycin; Clarithromycin EP Impurity D |
| Storage | Store at -20°C |
| IUPAC Name | (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione |
| Canonical SMILES | CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)NC)O)(C)OC)C)C)O)(C)O |
| InChI | InChI=1S/C37H67NO13/c1-14-25-37(10,44)30(41)20(4)27(39)18(2)16-36(9,46-13)32(51-34-28(40)24(38-11)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-35(8,45-12)31(42)23(7)48-26/h18-26,28-32,34,38,40-42,44H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1 |
| InChI Key | CIJTVUQEURKBDL-RWJQBGPGSA-N |
Properties
| Appearance | White to Pale Yellow Solid |
| Boiling Point | 804.5±65.0°C (Predicted) |
| Melting Point | 200-202°C |
| Density | 1.18±0.1 g/cm3 (Predicted) |
| Solubility | Slightly soluble in Chloroform (Sonicated), Methanol (Sonicated) |
Reference Reading
1.Aquatic toxicity of the macrolide antibiotic clarithromycin and its metabolites.
Baumann M1, Weiss K2, Maletzki D3, Schüssler W4, Schudoma D5, Kopf W6, Kühnen U7. Chemosphere. 2015 Feb;120:192-8. doi: 10.1016/j.chemosphere.2014.05.089. Epub 2014 Jul 20.
The human macrolide antibiotic clarithromycin is widespread in surface waters. Our study shows that its major metabolite 14-hydroxy(R)-clarithromycin is found in surface waters in comparable amounts. This metabolite is known to be pharmacologically active. Additionally, clarithromycin is partly metabolised to N-desmethyl-clarithromycin, which has no antimicrobial activity. For clarithromycin, some ecotoxicological studies on aquatic organisms have been published. However, many of them are not conform with the scientific principles as given in the "Technical guidance for deriving environmental quality standards" (TGD-EQS), because numerous studies were poorly documented and the methods did not contain analytical measurements confirming that the exposure concentrations were in the range of ± 20% of the nominal concentrations. Ecotoxicological effects of clarithromycin and its two metabolites on the zebrafish Danio rerio (embryo test), the microcrustacean Daphnia magna, the aquatic monocotyledonous macrophyte Lemna minor, the freshwater green alga Desmodesmus subspicatus (Chlorophyta) and the cyanobacterium Anabaena flosaquae were investigated in compliance with the TGD-EQS.
2.Oxidative metabolism of clarithromycin in the presence of human liver microsomes. Major role for the cytochrome P4503A (CYP3A) subfamily.
Rodrigues AD1, Roberts EM, Mulford DJ, Yao Y, Ouellet D. Drug Metab Dispos. 1997 May;25(5):623-30.
In vitro studies were conducted to identify the hepatic cytochrome P450 (CYP) protein(s) involved in the oxidative metabolism of [14C]clarithromycin (CLAR) in the presence of native human liver microsomes. The identity of the two major CLAR metabolites present in microsome incubates, 14-(R)-hydroxy-CLAR and N-desmethyl-CLAR, was confirmed by MS. Over the CLAR concentration range of 1.0-140 microM, the rate of CLAR 14-(R)-hydroxylation (KM = 48 +/- 17.7 microM; Vmax = 206 +/- 76 pmol/min/mg protein; Vmax/KM = 4.2 +/- 0.21 microliters/min/mg; mean +/- SD, N = 3 livers) and N-demethylation (KM = 59.1 +/- 24.0 microM; Vmax = 189 +/- 52.0 pmol/min/mg protein; Vmax/KM = 3.3 +/- 0.53 microliters/min/mg) conformed to monophasic (saturable) Michaelis-Menten kinetics and was highly correlated (r = 0.90-0.92; p < 0.001; N = 11) with CYP3A-selective erythromycin N-demethylase activity. Ketoconazole (< or = 2.0 microM) or troleadomycin, CYP3A-selective inhibitors, markedly decreased (> or = 99%) the formation of both metabolites, whereas inhibitors selective of other CYP forms were relatively ineffective (< or = 10% inhibition).
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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 ╳
