Roxithromycin

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Roxithromycin
Roxithromycin.svg
Roxithromycin ball-and-stick.png
Systematic (IUPAC) name
(3R,4S,5S,6R,7R,9R,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}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy cat.? (USA)
B1 (Aus)
Legal status?
Pharmacokinetic data
MetabolismLiver, peak concentration averaging 2 hours after ingestion.
Half-life11 hours
Identifiers
CAS number80214-83-1 YesY
ATC codeJ01FA06
PubChemCID 6915744
DrugBankDB00778
ChemSpider5291557 YesY
UNII21KOF230FA YesY
KEGGD01710 YesY
ChEBICHEBI:48935 YesY
ChEMBLCHEMBL1214185 YesY
Chemical data
FormulaC41H76N2O15 
Mol. mass837.047 g/mol
 YesY (what is this?)  (verify)
 
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This article is about the antibiotic Roxithromycin. For the Norwegian company see Roxar AS.

Roxithromycin
Roxithromycin.svg
Roxithromycin ball-and-stick.png
Systematic (IUPAC) name
(3R,4S,5S,6R,7R,9R,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}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy cat.? (USA)
B1 (Aus)
Legal status?
Pharmacokinetic data
MetabolismLiver, peak concentration averaging 2 hours after ingestion.
Half-life11 hours
Identifiers
CAS number80214-83-1 YesY
ATC codeJ01FA06
PubChemCID 6915744
DrugBankDB00778
ChemSpider5291557 YesY
UNII21KOF230FA YesY
KEGGD01710 YesY
ChEBICHEBI:48935 YesY
ChEMBLCHEMBL1214185 YesY
Chemical data
FormulaC41H76N2O15 
Mol. mass837.047 g/mol
 YesY (what is this?)  (verify)

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, Biaxsig, Coroxin, Romac, Roxar, Roximycin, Roxl-150, Roxo, Roxomycin, Rulid, Rulide, Surlid, Tirabicin and Xthrocin. Roxithromycin is not available in the United States. Roxithromycin is available in Australia. Roxithromycin has also been tested to possess antimalarial activity.

History[edit]

German pharmaceutical company Hoechst Uclaf brought out roxithromycin in 1987.

Available forms[edit]

Roxithromycin is commonly available as tablets or oral suspension.

Mechanism of action[edit]

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.

Pharmacokinetics[edit]

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.

Metabolism[edit]

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.

Side effects[edit]

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.

Drug interactions[edit]

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.

Drug Dosage[edit]

Adults: 150 mg twice a day or 300 mg once a day, 30 minutes before meals or 2 hours after. For children, it is 2.5 - 5.0 mg/kg of body weight, given in two divided doses per day. [2] Roxithromycin is administered orally. Adults are given 10 by 150 mg tablets for 5 days, with an option to repeat for a further 5 days if required.

References[edit]

  1. ^ "The Effect of 0.5% Roxithromycin Lotion for Androgenetic Alopecia - ClinicalTrials.gov". Retrieved 2007-09-22. 
  2. ^ Medical pharmacology, Ch.-54, ISBN 81_8448_085_7


External links[edit]