Roxithromycin

Structural formula
General
Non-proprietary name	Roxithromycin
other names	Erythromycin-9 - {( E ) - O - [(2-methoxyethoxy) methyl] oxime} Roxithromycinum ( Latin )
Molecular formula	C 41 H 76 N 2 O 15
External identifiers / databases
CAS number 80214-83-1 EC number 617-007-5 ECHA InfoCard 100.121.308 PubChem 6915744 DrugBank DB00778 Wikidata Q424037
Drug information
ATC code	J01 FA06
Drug class	Macrolide antibiotics
properties
Molar mass	837.05 g · mol -1
Physical state	firmly
Melting point	110-125 ° C
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	830 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Roxithromycin is an organic chemical compound from the group of glycosides , which as an antibiotically acting drug the group of macrolide antibiotics is used.

chemistry

Roxithromycin was made from erythromycin . The changes achieved are similar to clarithromycin .

pharmacology

application

Roxithromycin is used for infections of the respiratory tract, for infections in the ear, nose and throat area and for bacterial inflammation of the skin and the lower urinary tract. Roxithromycin can also be given for whooping cough and infections caused by Legionella , chlamydia and mycoplasma .

Mechanism of action

Roxithromycin belongs to the group of macrolide antibiotics. The mechanism of action of this group of substances is the inhibition of protein synthesis by binding to the 50S subunit of the ribosomes .

The macrolide antibiotics hinder the process of protein synthesis during elongation, i.e. the lengthening phase of the protein chain on the ribosome. By binding, they block the translocation , i.e. the shift of the peptidyl t-RNA from the donor to the acceptor site . This leads to a premature interruption of protein synthesis and thus to a bacteriostatic effect.

Side effects

The macrolide antibiotics are generally well tolerated. Allergic reactions are rather rare. Skin rashes, itching or joint swelling may occur as hypersensitivity reactions . Occasionally, side effects to the hearing apparatus can occur, this can be a temporary impairment of hearing and ear noises. Cardiac arrhythmias (including QT time lengthening) and changes in the liver tissue with an increase in special liver enzymes are rarely observed. On the other hand, side effects affecting the digestive tract are more common. It can be stomach pressure, nausea and vomiting, as well as diarrhea and flatulence. If diarrhea persists, pseudomembranous colitis must be ruled out. Cases of acute pancreatitis , i.e. inflammation of the pancreas, have been observed in isolated cases . In addition, when Roxithromycin is administered, disturbances of the sense of smell and taste are occasionally observed.

Interactions

Interactions in systemic use:

• other antibiotics:
  • If different macrolides are combined with one another, cross-resistance can occur. When combining macrolides with other antibiotics such as Cross- resistance has also been observed, for example lincosamides , clindamycin and chloramphenicol .
• certain anti-epileptic drugs , such as carbamazepine and valproic acid :
  • The concentration of carbamazepine and valproic acid in the blood can increase with the simultaneous administration of macrolides, which increases the risk of dangerous side effects of the anti-epileptic drugs.
• Theophylline:
  • If macrolide antibiotics and theophylline are given together, the levels of theophylline in the blood may increase.
• Ciclosporin:
  • If the immunosuppressant ciclosporin and macrolide antibiotics are administered at the same time , the kidney-damaging effect of ciclosporin increases.
• Terfenadine , Astemizole, and Cisapride :
  • If these active ingredients are administered together with erythromycin , there is a risk of life-threatening cardiac arrhythmias . A combined application is therefore prohibited.
• Digoxin:
  • Macrolides can increase the levels of digoxin in the blood.
• Methylprednisolone , Triazolam , Midazolam , Alfentanil , Felodipine and Coumarin-Type Anticoagulants :
  • With simultaneous use with macrolide antibiotics, the residence time of the named drugs in the body can increase, which increases their effect.
• Ergot alkaloids:
  • If dihydroergotamine and non-hydrogenated ergot alkaloids are given together with macrolides, increased vasoconstriction can occur. These drugs must therefore not be used together with roxithromycin.
• Omeprazole:
  • Omeprazole increases the bioavailability of roxithromycin. This means that if the dosage is unchanged, the amount of roxithromycin that is available to the body increases.

• Cholesterol-lowering drugs (statins, especially simvastatin ): The interaction between macrolides and statins is classified as serious by the ABDA database. There is a risk of myopathies and rhabdomyolysis. If the gift of z. B. Simvastatin must not be interrupted, then the dose must not exceed 10 mg / day during concomitant macrolide intake.

Contraindications

Contraindications for systemic use:

• Hypersensitivity to macrolides is a contraindication, as cross-reactions can occur within the group of macrolides.
• In the case of existing liver dysfunction and renal insufficiency, macrolides should only be used after careful consideration.
• For use in pregnant women, macrolides are among the preferred antibiotics, i.e. they are the means of choice. As always with the use on pregnant women, the guideline also applies here that older and therefore better known active ingredients are preferred. For the administration of macrolides, this means that preference is given to erythromycin.
• When given to nursing mothers, it must be noted that the macrolide antibiotics pass into breast milk, so the attending physician must carefully consider the prescription.

Trade names

Monopreparations

Rulid (D, CH), Rulide (A), numerous generics (D, A), Roxi (D)

Individual evidence

1. ↑ Entry on Roxithromycin. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.
2. ↑ ^{a b c} data sheet Roxithromycin from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !