Roxithromycin

Overview

Roxithromycin is a semi-synthetic macrolide antibiotic used to treat respiratory tract, urinary and soft tissue infections. It is a derivative of erythromycin - comprising the same 14-membered lactone ring - with an oxime-based side chain attached to the macrolide ring. WP

Roxithromycin was patented in 1980 and approved for medical use in 1987. It is available under several brand names in Australia, France, Germany, Israel, South Korea and New Zealand, but not in the United States. Roxithromycin has also been shown to possess antimalarial activity.[1] WP⚠ Wikipedia itself has flagged this text: citation needed.

Uses, dosage and effects

Available forms

Roxithromycin is commonly available as tablets or oral suspension. WP⚠ Wikipedia itself has flagged this text: citation needed.

Risks and side effects

Side effects

The most common side effects are gastrointestinal: diarrhea, nausea, abdominal pain and vomiting. Less common side effects include central or peripheral nervous system events such as headaches, dizziness, and vertigo. Rarely seen side effects are rashes, abnormal liver function values and alteration in the senses of smell and taste. WP⚠ Wikipedia itself has flagged this text: citation needed.

Interactions

Drug interactions

Roxithromycin has fewer interactions than erythromycin as it has a lower affinity for cytochrome P450. WP

Roxithromycin is not known to interact with hormonal contraceptives, prednisolone, carbamazepine, ranitidine or antacids. WP

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. WP

Roxithromycin appears to interact with warfarin. This is shown by an increase in prothrombin time and/or international normalised ratio (INR) in patients taking roxithromycin and warfarin concurrently. As a consequence, severe bleeding episodes have occurred.[2] WP

Pharmacology

Mechanism of action

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 synthesis of peptides. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila. WP⚠ Wikipedia itself has flagged this text: citation needed.

Pharmacokinetics

When taken before a meal, roxithromycin is very rapidly absorbed, and diffuses 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. WP⚠ Wikipedia itself has flagged this text: citation needed.

History

History

French pharmaceutical company Roussel Uclaf first marketed roxithromycin in 1987. WP

Chemistry

Formula

C41H76N2O15 PC

CAS number

80214-83-1 PC

Molar mass (g/mol)

837.0 PC

IUPAC name (computed by PubChem)

(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-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-oxacyclotetradecan-2-one PC

SMILES

CC[C@@H]1[C@@]([C@@H]([C@H](/C(=N/OCOCCOC)/[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O PC

InChIKey

RXZBMPWDPOLZGW-XMRMVWPWSA-N PC

PubChem CID

6915744

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
2. Journal / agency Savage RL, Tatley MV. Case Series Analysis of New Zealand Reports of Rapid Intense Potentiation of Warfarin by Roxithromycin. Drug Safety. May 2018. doi:10.1007/s40264-017-0634-y · PMID 29330715 · PMC5938301

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.