Tetracycline

Tetracycline
ATC Code A01AB13, D06AA04, D10AF08, J01AA07, S01AA09, S02AA08, S03AA02
Formula C22H24N2O8
Molar Mass (g·mol−1) 444,44
Physical State solid
Melting Point (°C) 172
PKS Value 3.3
CAS Number 60-54-8
PUB Number 54675776
Drugbank ID DB00759
Solubility poorly soluble in water / highly soluble in ethanol

Basics

Tetracycline is a broad-spectrum antibiotic produced by the Streptomyces genus of actinobacteria. It has a bacteriostatic effect on a wide range of gram-positive and gram-negative pathogens. It is used to treat a number of infections. These include acne, cholera, brucellosis, plague, malaria, and syphilis. It is taken by mouth. Tetracycline requires a prescription and is on the World Health Organization's list of essential medicines.

Pharmacology

Pharmacodynamics

Tetracycline passively diffuses through pore channels in the bacterial membrane and reversibly binds to the 30S ribosomal subunit, preventing tRNA binding to the mRNA-ribosome complex and thus interfering with protein synthesis. As a result, bacteria are unable to proliferate further and can be more easily eliminated by the immune system.

Pharmacokinetics

Bioavailability is less than 40% with intramuscular administration, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral tetracycline preparations by 50% or more. Plasma protein binding is approximately 20-70%. Excretion is by the kidney and the half-life is 6-12 hours.

Drug Interactions

Tetracycline may be inactivated by iron, aluminum or calcium. Therefore, dairy products, iron supplements, and antacids should be avoided while taking it.

Toxicity

Side effects:

  • Yellowing of the teeth.
  • photosensitivity of the skin, so exposure to the sun or intense light is not recommended
  • drug-induced lupus and hepatitis
  • fatty liver
  • Tinnitus

Toxicological data

LD50 (mouse,oral): 678 mg-kg-1

Sources

  • Drugbank
  • PubChem
  • Aktories, Förstermann, Hofmann, Starke: Allgemeine und spezielle Pharmakologie und Toxikologie, Elsvier, 2017
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.

Your personal medicine assistent

afgis-Qualitätslogo mit Ablauf Jahr/Monat: Mit einem Klick auf das Logo öffnet sich ein neues Bildschirmfenster mit Informationen über Medikamio GmbH & Co KG und sein/ihr Internet-Angebot: medikamio.com/ This website is certified by Health On the Net Foundation. Click to verify.
Drugs

Search our database for drugs, sorted from A-Z with their effects and ingredients.

Substances

All substances with their common uses, chemical components and medical products which contain them.

Diseases

Causes, symptoms and treatment for the most common diseases and injuries.

The contents shown do not replace the original package insert of the medicinal product, especially with regard to dosage and effect of the individual products. We cannot assume any liability for the correctness of the data, as the data was partly converted automatically. A doctor should always be consulted for diagnoses and other health questions. Further information on this topic can be found here.