Decladinose Roxithromycin
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| Category | Others |
| Catalog number | BBF-04334 |
| CAS | 214902-82-6 |
| Molecular Weight | 678.85 |
| Molecular Formula | C33H62N2O12 |
| Purity | >95% |
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Description
An impurity found in the macrolide antibiotic, Roxithromycin.
Specification
| Synonyms | 3-O-de(2,6-dideoxy-3-C-methyl-3-O-methyl-α-Lribo-hexopyranosyl)erythromycin 9-(E)-[O-[(2-methoxyethoxy)methyl]oxime]; Decladinosylroxithromycin; Roxithromycin Impurity B; (9E)-3-O-de(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)erythromycin9-[O-[(2-Methoxyethoxy)methyl]oxime] |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-4,7,12,13-tetrahydroxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one |
| Canonical SMILES | CCC1C(C(C(C(=NOCOCCOC)C(CC(C(C(C(C(C(=O)O1)C)O)C)OC2C(C(CC(O2)C)N(C)C)O)(C)O)C)C)O)(C)O |
| InChI | InChI=1S/C33H62N2O12/c1-12-24-33(8,41)28(38)20(4)25(34-44-17-43-14-13-42-11)18(2)16-32(7,40)29(21(5)26(36)22(6)30(39)46-24)47-31-27(37)23(35(9)10)15-19(3)45-31/h18-24,26-29,31,36-38,40-41H,12-17H2,1-11H3/b34-25+/t18-,19-,20+,21+,22-,23+,24-,26+,27-,28-,29-,31+,32-,33-/m1/s1 |
| InChI Key | BNZRPTCUAOMSSH-MDOVVVHDSA-N |
Properties
| Appearance | Pale Yellow Solid |
| Boiling Point | 773.9±70.0°C (Predicted) |
| Melting Point | 89-95°C |
| Density | 1.24±0.1 g/cm3 (Predicted) |
| Solubility | Slightly soluble in DMSO, Methanol, Water |
Reference Reading
1. [Metabolism of roxithromycin in dogs]
Da-fang Zhong, Li-feng Zhang, Shu-qiu Zhang, Jie Xing Yao Xue Xue Bao . 2003 May;38(5):374-9.
Aim:To investigate the metabolic profile of roxithromycin in dogs and the effects of oral and intravenous administrations on the metabolism of roxithromycin.Methods:Liquid chromatography-tandem mass spectrometry (LC-MSn) was used for separation and analysis of roxithromycin and its metabolites in dog bile after an oral dose or intravenous dose of roxithromycin. The metabolites were identified by comparisons of their mass spectra and LC behaviors with the references.Results:Totally 13 metabolites were detected in dog bile, including N-demethylated derivatives, N, N-didemethylated derivatives, O-dealkylether derivatives, decladinose derivatives, and the geometric isomers of parent drug and its metabolites.Conclusion:Roxithromycin underwent 4 metabolic pathways in which geometric isomerization and decladinose metabolism were found to be markedly different between the two administration routes.
2. pH-dependent geometric isomerization of roxithromycin in simulated gastrointestinal fluids and in rats
Dafang Zhong, Shuqiu Zhang, Jie Xing J Pharm Sci . 2004 May;93(5):1300-9. doi: 10.1002/jps.20023.
The biotransformation of roxithromycin in simulated gastrointestinal fluids at 37 degrees C and in rats was investigated by using liquid chromatography-tandem mass spectrometry. Roxithromycin degraded to its Z-isomer and decladinose derivative in simulated gastrointestinal fluids in vitro at pH
3. Quantification of clarithromycin, its 14-hydroxy and decladinose metabolites in rat plasma, gastric juice and gastric tissue using high-performance liquid chromatography with electrochemical detection
P N Shaw, J I D Wibawa, D A Barrett J Chromatogr B Analyt Technol Biomed Life Sci . 2003 Jan 15;783(2):359-66. doi: 10.1016/s1570-0232(02)00765-1.
A rapid, selective and sensitive HPLC assay has been developed for the simultaneous analysis of clarithromycin, its 14-hydroxy-clarithromycin metabolite, and its decladinose acid degradation product, in small volumes of rat gastric juice aspirate, plasma and gastric tissue. Sample were extracted with n-hexane/2-butanol (4:1) and the internal standard was roxithromycin. A Kromasil ODS 5 micrometer(75x4.6 mm I.D.) column was used with a mobile phase consisting of acetonitrile/aqueous phosphate buffer (pH 7, 0.086 M) (45:55 v/v). The column temperature was 30 degrees C and coulometric detection was used at 850 mV using a screen voltage of 600 mV. The analysis time was less than 8 min. The limits of quantitation for clarithromycin, 14-OH clarithromycin and decladinose clarithromycin were 0.15 microgram ml(-1) or lower in plasma (0.05 ml); 0.16 microgram ml(-1) or lower in gastric juice (0.2 ml); and 0.51 microgram g(-1) or lower for gastric tissue (0.25 g). The method was linear up to at least 20.3, 15.4 and 12.5 microgram ml(-1) for clarithromycin, 14-OH-clarithromycin and decladinose, respectively, in gastric juice aspirate and plasma and up to 40.6, 30.9 and 25.0 microgram g(-1) in gastric tissue. The assay was applied to the measurement of clarithromycin, 14-OH-clarithromycin and, for the first time, decladinose clarithromycin in pharmacokinetic studies of gastric transfer of clarithromycin in individual rats.
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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 ╳
