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Tetracycline
- 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 | |
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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 D06AA04 J01AA07 S01AA09 S02AA08 S03AA02 |
| PubChem | |
| DrugBank | |
| 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 bacterium, 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 antibiotic group.
Mode of action
It works by inhibiting action of the prokaryotic 30S ribosome, by binding aminoacyl-tRNA. However, bacteria strains can aquire resistance against tetracycline and its derivates by encoding a resistance operon.
In eukaryotic cells, toxicity may be 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.
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
Indication
Tetracycline's primary use is for the treatment of acne vulgaris and rosacea.
It is also used to treat a very wide range of infections; see tetracycline antibiotics for details.
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.
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
| Stomatological preparations (A01) | |
|---|---|
| Caries prophylactic agents | Sodium fluoride - Sodium monofluorophosphate - Olaflur - Stannous fluoride |
| Anti-infectives and antiseptics | Hydrogen peroxide - Chlorhexidine - Amphotericin B - Polynoxylin - Domiphen - Oxyquinoline - Neomycin - Miconazole - Natamycin - Hexetidine - Tetracycline - Benzoxonium chloride - Tibezonium iodide - Mepartricin - Metronidazole - Clotrimazole - Sodium perborate - Chlortetracycline - Doxycycline - Minocycline - Eugenol |
| Corticosteroids | Triamcinolone - Dexamethasone - Hydrocortisone |
| Other | Epinephrine/Adrenalone - Benzydamine - Acetylsalicylic acid - Amlexanox |
| [hide] Antibiotics and chemotherapeutics for dermatological use (D06) | |
|---|---|
| Antibiotics: tetracycline and derivatives | Demeclocycline - Chlortetracycline - Oxytetracycline - Tetracycline |
| Antibiotics: other | Fusidic acid - Chloramphenicol - Neomycin - Bacitracin - Gentamicin - Tyrothricin - Mupirocin - Virginiamycin - Rifaximin - Amikacin |
| Chemotherapeutics: sulfonamides | Silver sulfadiazine - Sulfathiazole - Mafenide - Sulfamethizole - Sulfanilamide - Sulfamerazine |
| Chemotherapeutics: antivirals | Idoxuridine - Tromantadine - Aciclovir - Podophyllotoxin - Inosine - Penciclovir - Lysozyme - Ibacitabine - Edoxudine - Imiquimod - Docosanol |
| Chemotherapeutics: other | Metronidazole |
| [hide] Acne-treating agents (D10) | |
|---|---|
| Topical agents | Azelaic acid • Benzoyl peroxide • Glycolic acid • Light therapy • Salicylic acid • Tea tree oil |
| Antibiotics | Clindamycin • Erythromycin • Sulfacetamide • Tetracyclines • Trimethoprim |
| Hormonal | Antiandrogens • Contraceptives |
| Retinoids | Adapalene • Isotretinoin • Tazarotene • Tretinoin |
| [hide] Antibacterials for systemic use: tetracycline antibiotics (J01A) | |
|---|---|
| Tetracyclines | Chlortetracycline • Clomocycline • Demeclocycline • Doxycycline • Lymecycline �� Metacycline • Minocycline • Oxytetracycline • Penimepicycline • Rolitetracycline • Tetracycline |
| Glycylcyclines | Tigecycline |
| [hide] Otologicals (S02) | |
|---|---|
| Anti-infectives | Chloramphenicol - Nitrofural - Boric acid - Aluminium acetotartrate - Clioquinol - Hydrogen peroxide - Neomycin - Tetracycline - Chlorhexidine - Acetic acid - Polymyxin B - Rifamycin - Miconazole - Gentamicin |
| Corticosteroids | Hydrocortisone - Prednisolone - Dexamethasone - Betamethasone |
| Other otologicals | Lidocaine - Cocaine |
The content of this section is licensed under the GNU Free Documentation License (local copy). It uses material from the Wikipedia article "Tetracycline" modified December 22, 2007 with previous authors listed in its history.
