| Systematic (IUPAC) name | |
|---|---|
| (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-d-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-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | ? (USA) B1 (Aus) |
| Legal status | ? |
| Pharmacokinetic data | |
| Metabolism | Liver, peak concentration averaging 2 hours after ingestion. |
| Half-life | 12 hours |
| Identifiers | |
| CAS number | 80214-83-1 |
| ATC code | J01 |
| PubChem | CID 6915744 |
| DrugBank | APRD01305 |
| ChemSpider | 5291557 |
| UNII | 21KOF230FA |
| KEGG | D01710 |
| ChEBI | CHEBI:48935 |
| ChEMBL | CHEMBL1214185 |
| Chemical data | |
| Formula | C41H76N2O15 |
| Mol. mass | 837.047 g/mol |
| SMILES | eMolecules & PubChem |
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Roxithromycin is a semi-synthetic macrolide antibiotic. It is used to treat respiratory tract, urinary and soft tissue infections. Roxithromycin is derived from erythromycin, containing the same 14-membered lactone ring. However, an N-oxime side chain is attached to the lactone ring. It is also currently undergoing clinical trials for the treatment of male-pattern hair loss.[1]
Roxithromycin is available under several brandnames, for example, Xthrocin, Roxl-150, Roxo, Surlid, Rulide, Biaxsig, Roxar, Roximycin, Roxomycin, Rulid, Tirabicin and Coroxin. Roxithromycin is not available in the United States. Roxithromycin has also been tested to possess antimalarial activity.
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German pharmaceutical company Hoechst Uclaf brought out roxithromycin in 1987.
Roxithromycin is commonly available as tablets or oral suspension.
Roxithromycin prevents bacteria from growing, by interfering with their protein synthesis. Roxithromycin binds to the subunit 50S of the bacterial ribosome, and thus inhibits the translocation of peptides. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila.
When taken before a meal, roxithromycin is very rapidly absorbed, and diffused into most tissues and phagocytes. Due to the high concentration in phagocytes, roxithromycin is actively transported to the site of infection. During active phagocytosis, large concentrations of roxithromycin are released.
Only a small portion of roxithromycin is metabolised. Most of roxithromycin is secreted unchanged into the bile and some in expired air. Under 10% is excreted into the urine. Roxithromycin's half-life is 12 hours.
Most common side effects are gastrointestinal; diarrhoea, nausea, abdominal pain and vomiting. Less common side effects include central or peripheral nervous system events such as headaches, dizziness, vertigo, and also the rarely seen rashes, abnormal liver function values and alteration in senses of smell and taste.
Roxithromycin has fewer interactions than erythromycin as it has a lower affinity for cytochrome P450.
Roxithromycin does not interact with hormonal contraceptives, prednisolone, carbamazepine, ranitidine or antacids.
When roxithromycin is administered with theophylline, some studies have shown an increase in the plasma concentration of theophylline. A change in dosage is usually not required but patients with high levels of theophylline at the start of the treatment should have their plasma levels monitored.
Roxithromycin appears to interact with warfarin. This is shown by an increase in prothrombin time (international normalised ratio [INR]) in patients taking roxithromycin and warfarin concurrently. As a consequence, severe bleeding episodes have occurred.
Adults: 150 mg twice in a day, 1–2 hours before meals. For children, it is 2.5 - 5.0 mg/kg of body weight, given in two divided doses per day. [2] Mode of Administration- Oral.
Stability of roxithromycin was studied by Wei Zhenping et al[4] in solutions of different pH values were determined separately by colorimetry, TLC and HPLC. Oh-Seung Kwon et al[5] evaluated the bioequivalency between different brands of Roxithromycin Tablets administered to healthy Korean male volunteers using HPLC with fluorescence detector. The reversed-phase (RP) chromatographic behaviour of the macrolide antibiotics clarithromycin (Clari) and roxithromycin (Roxi) was extensively studied by A. Pappa-louisi et al[6] as a function of mobile phase composition - modified with one, two or three of organic solvents - and column temperature. A rapid and sensitive reverse phase high performance liquid chromatographic method with UV detection was developed by Prafulla Sahu et al[7] for the determination of Roxithromycin present in bulk and pharmaceutical dosage forms. A selective HPLC method with fluorescence detection for the determination of roxithromycin (ROX) in human plasma was described by Franciszek K. Główka et al.[8] After solid-phase extraction (SPE), ROX and erythromycin (internal standard, I.S.) were derivatized by treatment with 9-fluorenylmethyl chloroformate (FMOC-Cl). Optimal resolution of fluorescence derivatives of ROX and I.S. was obtained during one analytical run using reversed phase, C18 column. The mobile phase was composed of potassium dihydrogenphosphate solution, pH 7.5 and acetonitrile. Fluorescence of the compounds was measured at the maximum excitation, 255 nm and emission, 313 nm, of ROX derivatives. A method for the determination of Roxithromycin in the flounder muscle by LC–MS was developed by Jong-hwan Lim et al.[9] A dichloromethane extract of the sample was separated on C18 reversed-phase column with acetonitrile–50 mM ammonium acetate (80:20, v/v) as the mobile phase and analyzed by LC–MS via atmospheric pressure ionization/ electrospray ionization interface. Jin Sun et al[10] described the impact of pharmaceutical dosage forms on the pharmacokinetics of roxithromycin in healthy human volunteers and characterization of roxithromycin degradation in simulated gastric fluid and simulated intestinal fluid using high performance liquid chromatography (HPLC)-tandem MS. A stability indicating reverse phase high performance liquid chromatographic method is developed by Dhiraj S. Nikam et al[11] for simultaneous estimation of ambroxol hydrochloride and roxithromycin in bulk and pharmaceutical formulation using water: acetonitrile: orthophosphoric acid (50:50:0.1) as a mobile phase. Detection was carried out at 210 nm. An isocratic liquid chromatographic method has been developed by H. K. Chepkwony et al[12] for the analysis of bulk samples of Roxithromycin using acetonitrile-2.0M (NH4)2HPO4, pH 6.4-water, 25∶30∶45, (v/v) as mobile phase detection was by UV absorbance at 215 nm. Sufficient separation of roxithromycin from its homolog containing one more methyleneoxy group (roxithromycin G) and from other related substances was achieved. Valéria de Oliveira et al[13] described a High-Performance Liquid Chromatographic method for the determination of Roxithromycin in Tablets using 0.067 M phosphate buffer, pH 4.0 and methanol (65:35) as mobile phase and UV detection at 210 nm. A liquid chromatography–mass spectrometry (LC–MS) method for the determination of roxithromycin in rat lung tissue is described by Peng Wang et al.[14] Chen Nai-jiang et al[15] described a HPLC-ELSD method for content determination of Roxithromycinusing methanol-0.2% trifluoroacetic acid(TFA) solution(50:50)(pH was adjusted to 6.5 with triethylamine) as mobile phase at room temperature and ELSD as detector. Dafang Zhong et al[16] identified various metabolites of Roxithromycin in human biological fluids. A total of 15 metabolites were found in bile, urine, and plasma by HPLC with ion trap mass spectrometric and electrochemical detection.
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