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- This article deals with the specific antibiotic called tetracycline. For the group of antibiotics known as the tetracyclines, see tetracycline antibiotics.
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Tetracycline
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| Systematic (IUPAC) name | |
| 2-(amino-hydroxy-methylidene)-4-dimethylamino- 6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5, 5a-tetrahydrotetracene-1,3,12-trione OR 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro- 3,6,10,12,12a-pentahydroxy- 1,11dioxo-naphthacene-2carboxamide |
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| Identifiers | |
| CAS number | |
| ATC code | A01 D06 J01 S01 S02 S03 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C22H24N2O8 |
| Mol. mass | 444.435 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 60-80% Oral, while fasting <40% Intramuscular |
| Metabolism | Not metabolised |
| Half life | 6-11 hours |
| Excretion | Fecal and Renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status |
℞ Prescription only |
| Routes | oral, topical (skin & eye), im, iv |
Tetracycline (INN) (pronounced /ˌtɛtrəˈsaɪkliːn/) is a broad-spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria, indicated for use against many bacterial infections. It is commonly used to treat acne. It is sold under the brand names Sumycin, Terramycin, Tetracyn, and Panmycin, among others. Actisite is a thread-like fiber form, used in dental applications. It is also used to produce several semi-synthetic derivatives, which together are known as the tetracycline antibiotics.
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Mode of action
It works by inhibiting action of the prokaryotic 30S ribosome, by binding the 16S rRNA thereby blocking the aminoacyl-tRNA. However, bacteria strains can acquire resistance against tetracycline and its derivates by encoding a resistance operon.
In eukaryotic cells, toxicity may be the result of inactivation of mitochondrial 30S ribosomes.
History
The tetracyclines are a large family of antibiotics that were discovered as natural products by Benjamin Minge Duggar and first described in 1948.1 Tetracycline was then discovered by Lloyd Conover in the research departments of Pfizer. The patent for tetracycline, U.S. Patent 2,699,054, was first issued in 1950. However, Nubian mummies have been studied in the 1990s and were found to contain significant levels of tetracycline; there is evidence that the beer brewed at the time could have been the source.2 Tetracycline sparked the development of many chemically altered antibiotics and in doing so has proved to be one of the most important discoveries made in the field of antibiotics. It is used to treat many gram-positive and gram-negative bacteria and some protozoa. It, like some other antibiotics, is also used in the treatment of acne.
Cautions, contraindications, side effects
Are as those of the tetracycline antibiotics group:
- Can stain developing teeth (even when taken by the mother during pregnancy)
- Inactivated by Ca2+ ion, not to be taken with milk or yogurt
- Inactivated by aluminium, iron and zinc, not to be taken at the same time as indigestion remedies
- Inactivated by common antacids and over-the-counter heartburn medicines.
- Skin photosensitivity; exposure to the Sun or intense light is not recommended
- Drug-induced lupus, and hepatitis
- Tinnitus
- When used for acne vulgaris, skin can be extremely dry and flaky if overused
- May interfere with methotrexate by displacing it from the various protein binding sites
- Can cause breathing complications as well as anaphylactic shock in some individuals
Indication
Tetracycline's primary use is for the treatment of acne vulgaris and rosacea.
Other uses
Since tetracycline is absorbed into bone, it is used as a marker of bone growth for biopsies in humans, and as a biomarker in wildlife to detect consumption of medicine- or vaccine-containing baits.3 The presence of tetracycline in bone is detected by its fluorescence.4
In genetic engineering tetracycline is used in transcriptional activation. Tetracycline is also one of the antibiotics used to treat ulcers caused by bacterial infections. In cancer research at Harvard Medical School, tetracycline has been used to reliably cause regression of advanced stages of leukemia in mice, by putting this inexpensive antibiotic into their drinking water.5
Cell Culture
Tetracycline is used in cell biology as selective agent in cell culture systems. It is toxic to prokaryotic and eukaryotic cells and selects for cells harboring the bacterial tetr gene, which encodes a 399-amino acid membrane associated protein. This protein actively exports tetracycline out of the cell rendering cells harboring this gene more resistant to the drug. The yellow crystalline powder can be dissolved in water (20mg/ml) or ethanol (5mg/ml) and is routinely used at 10mg/L in cell culture. In cell culture at 37oCelsius it is stable for 4 days.
References
- ^ Klajn, Rafal, Chemistry and chemical biology of tetracyclines, retrieved 20 June 2007.
- ^ George Armelagos (May, 2000). "Take Two Beers and Call Me in 1,600 Years - use of tetracycline by Nubians and Ancient Egyptians". American Museum of Natural History. Retrieved on 2007-12-19.
- ^ Olson CA, et al. Bait ingestion by free-ranging raccoons and nontarget species in an oral rabies vaccine field trial in Florida. J Wildl Dis. 2000 Oct;36(4):734-43.
- ^ Mayton CA. Tetracycline labeling of bone
- ^ William J. Cromie (February 10, 2000). "Researchers Switch Cancer Off and On -- In Mice". Retrieved on 2008-10-25.
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Wikipedia content modification information:
- This page was last modified on 30 November 2008, at 20:27.
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