Clarithromycin

Clarithromycin
ATC Code J01FA09
Formula C38H69NO13
Molar Mass (g·mol−1) 747,95
Physical State solid
Melting Point (°C) 225,7
PKS Value 8,99
CAS Number 81103-11-9
PUB Number 84029
Drugbank ID DB01211
Solubility sparingly soluble in water

Basics

Clarithromycin, a semisynthetic macrolide antibiotic derived from erythromycin. It is used to treat various bacterial infections. These include streptococcal infections, pneumonia, skin infections, H. pylori infections, and Lyme disease. Clarithromycin can be bacteriostatic or bactericidal, depending on the organism and the concentration of active ingredient. It is taken in the form of tablets or liquid.

Clarithromycin was discovered and patented in 1980 by researchers at Taisho Pharmaceutical, a Japanese drug company, and first approved for medical use in Japan and the United States in 1991. It is on the World Health Organization's list of essential medicines.

Pharmacology

Pharmacodynamics

Like other macrolide antibiotics, clarythromycin penetrates the cell wall of bacteria and reversibly binds to domain V of the 23S ribosomal RNA of the 50S subunit of the bacterial ribosome. This blocks the translocation of aminoacyl transfer RNA and polypeptide synthesis. As a result, the bacterial cells can no longer produce proteins and are therefore unable to reproduce. After ingestion, claryhtromycin is partially converted into the metabolite 14-OH-clarithromycin, which is also active and acts synergistically with the parent compound.

Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.

Pharmacokinetics

Clarithromycin is well absorbed after oral administration, is acid stable, and can be taken with food. Bioavailability is approximately 50%. It is approximately 70% bound to plasma proteins in the blood. It is metabolized predominantly by the enzyme CYP3A4 in the liver. This may result in a number of drug-drug interactions. The elimination half-life is approximately 3-4 hours.

Drug Interactions

Clarithromycin inhibits the liver enzyme, CYP3A4, which is involved in the metabolism of many other commonly prescribed drugs. Taking clarithromycin together with other drugs metabolized by CYP3A4 may result in unexpected increases or decreases in plasma levels of these agents.

Drugs with a high risk for interactions include:

  • Colchicine (risk of fatal colchicine toxicity result, especially in people with chronic kidney disease).
  • Statins (risk of severe muscle pain and rhabdomyolysis).
  • Verapamil (risk for hypotension, bradycardia, and lactic acidosis)
  • Carbamazepine (risk for seeing double vision, dizziness, ataxia, and hyponatremia)
  • HIV medications (plasma levels and effect may be reduced)

Toxicity

Side effects

The most common side effects include:

  • Diarrhea
  • Nausea
  • Abdominal pain
  • Vomiting
  • Headache
  • Insomnia
  • Abnormal liver function tests

Less common side effects (<1%) include extreme irritability, prolongation of the QT interval, hallucinations (auditory and visual), dizziness/motion sickness, and changes in the sensation of smell and taste, including a metallic taste. Dry mouth, panic attacks, and nightmares may also occur.

Contraindications

  • Hypersensitivity to the active substance
  • Hypokalemia (low level of potassium in the blood) being used
  • Taking together with colchicine in people with kidney or liver dysfunction.
  • Concomitant use with cholesterol-lowering agents such as lovastatin or simvastatin
  • QT prolongation or ventricular arrhythmias, including torsade de pointes

The use of clarithromycin together with the following drugs is not recommended: Cisapride, pimozide, astemizole, terfenadine, ergotamine, ticagrelor, ranolazine, or dihydroergotamine.

Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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