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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.

Tetracycline

Systematic (IUPAC) name

2-(amino-hydroxy-methylidene)-4-dimethylamino-

6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,

5a-tetrahydrotetracene-1,3,12-trioneOR

4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-

3,6,10,12,12a-pentahydroxy-

1,11-dioxo-naphthacene-2-carboxamide

OR

(4S ,6S ,12aS )-4-(dimethylamino)- 3,6,10,12,12a-pentahydroxy- 6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-

octahydrotetracene-2-carboxamide

Identifiers

CAS number 60-54-8 [1]

64-75-5 [2]

(hydrochloride)

ATC code A01 AB13 [3] D06 AA04 [4] J01 AA07 [5] S01 AA09 [6] S02 AA08 [7] S03 AA02 [8] QG01 AA90 [9] QG51

AA02 [10]

 QJ51 AA07 [11]

PubChem CID 643969 [12]

DrugBank DB00759 [13]

ChemSpider 10257122 [14]

Chemical data

Formula C22

H24

N2O

8

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. D(AU) D(US)

Legal status Prescription only

Routes oral, topical (skin & eye), im, iv

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 (what is this?)  (verify) [15]

Tetracycline (INN) (pronounced / ̩tɛtrəˈsaɪkliːn/ ) is a broad-spectrum polyketide antibiotic produced by the

Streptomyces genus of Actinobacteria, indicated for use against many bacterial infections. It is a protein synthesis

inhibitor. It is commonly used to treat acne today, and, more recently, rosacea, and played a historical role in

reducing the incidence of mortality because of cholera. 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.

Mechanism of action

Tetracycline antiporter

system

Tetracyclines work by binding the 30S ribosomal subunit and through an interaction with

16S rRNA, they prevent the docking of amino-acylated tRNA.[16]

Resistance to tetracyclines can arise through drug efflux, ribosomal protection proteins,

16S rRNA mutation, and drug inactivation through the action of a monooxygenase.[17]

History

The tetracyclines are a large family of antibiotics that were discovered as natural products by Benjamin Minge

Duggar and first described in 1948.[18]

Under Yellapragada Subbarao, Benjamin Duggar made his discovery of the

world's first tetracycline antibiotic, Aureomycin, in 1945.

In 1950, Harvard Professor Robert Woodward determined the chemical structure of Terramycin, the brand name for

a member of the tetracycline family; the patent [19] protection for its fermentation and production was also first

issued in 1950. A research team of seven scientists at Pfizer [20], in collaboration with Woodward, participated in

the two-year research leading to the discovery [21].

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.[22]

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-effectsAre as those of the tetracycline antibiotics group:

• Can stain developing teeth (even when taken by the mother during pregnancy)

• Can cause permanent teeth discoloration (yellow-gray-brown); infancy and childhood to eight (8) years old

• Inactivated by Ca2+

ion, not to be taken with milk, yogurt, and other dairy products

• 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

• Can induce microvesicular fatty liver.

• Tinnitus

• May interfere with methotrexate by displacing it from the various protein binding sites

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• Can cause breathing complications as well as anaphylactic shock in some individuals

• Should be avoided during pregnancy as it may affect bone growth of fetus.

• Passes into breast milk and is harmful to breast-fed infants, and should therefore be avoided during breastfeeding

if possible.[23]

IndicationIt is first-line therapy for Rocky Mountain spotted fever (Rickettsia), Q fever (Coxiella), Psittacosis and

Lymphogranuloma venereum (Chlamydia), and to eradicate nasal carriage of meningococci. Tetracycline tablets

were used in the plague outbreak in India in 1992.[24]

Doxycycline is also one (of many) recommended drugs for chemoprophylatic treatment of malaria in travels to areas

of the world where malaria is endemic.[25]

Other uses

Since tetracycline is absorbed into bone, it is used as a marker of bone growth for biopsies in humans. Tetracycline

labeling is used to determine the amount of bone growth within a certain period of time, usually a period of approximately 21 days. Tetracycline is incorporated into mineralizing bone and can be detected by its

fluorescence.[26]

In double tetracycline labeling, a second dose is given 11-14 days after the first dose, and the

amount of bone formed during that interval can be calculated by measuring the distance between the two fluorescent

labels.[27]

Tetracycline is also used as a biomarker in wildlife to detect consumption of medicine- or vaccine-containing

baits.[28]

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 placing it in their drinking

water.[29]

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 (20 mg/ml) or ethanol (5 mg/ml) and is routinely

used at 10 mg/l in cell culture. In cell culture at 37 °C, it is stable for 4 days.

References

[1] http://www. nlm.  nih. gov/cgi/mesh/2009/MB_cgi?term=60-54-8&rn=1

[2] http://toolserver. org/~magnus/cas.php?language=en&cas=64-75-5&title=

[3] http://www. whocc.  no/atc_ddd_index/?code=A01AB13

[4] http://www. whocc.  no/atc_ddd_index/?code=D06AA04

[5] http://www. whocc.  no/atc_ddd_index/?code=J01AA07

[6] http://www. whocc.  no/atc_ddd_index/?code=S01AA09

[7] http://www. whocc.  no/atc_ddd_index/?code=S02AA08

[8] http://www. whocc.  no/atc_ddd_index/?code=S03AA02

[9] http://www. whocc.  no/atcvet/atcvet_index/?code=QG01AA90

[10] http://www. whocc. no/atcvet/atcvet_index/?code=QG51AA02

[11] http://www. whocc. no/atcvet/atcvet_index/?code=QJ51AA07

[12] http://pubchem. ncbi. nlm.  nih.gov/summary/summary.cgi?cid=643969

[13] http://www. drugbank.  ca/cgi-bin/show_drug.cgi?CARD=DB00759

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[14] http://www. chemspider. com/Chemical-Structure.10257122

[15] http://en. wikipedia. org/w/index.  php?&diff=cur&oldid=265711091

[16] Alekshun, M. N. & Levy, S. B. Molecular Mechanisms of Antibacterial Multidrug Resistance. Cell, 128, 1037-1050 (2007).

[17] Zakeri, B. & Wright, G. D. Chemical biology of tetracycline antibiotics. Biochem. Cell Biol. 86, 124-136 (2008).

[18] Klajn, Rafal, Chemistry and chemical biology of tetracyclines (http://www. chm.  bris. ac. uk/motm/tetracycline/tetracycline.  htm),

retrieved 20 June 2007.

[19] http://www. freepatentsonline.com/2516080.  pdf 

[20] http://www.  jstor. org/stable/3931295

[21] http://pubs. acs. org/doi/pdf/10.1021/ja01118a001

[22] George Armelagos (May, 2000). "Take Two Beers and Call Me in 1,600 Years - use of tetracycline by Nubians and Ancient Egyptians"

(http://www.  findarticles. com/p/articles/mi_m1134/is_4_109/ai_62324477). American Museum of Natural History. . Retrieved

2007-12-19.

[23] kidsgrowth.org --> Drugs and Other Substances in Breast Milk (http://www.  kidsgrowth. org/resources/articledetail.  cfm?id=471)

Retrieved on June 19, 2009

[24] Lippincott's Illustrated Reviews: Pharmacology, 4th ed. Harvery RA, Champe, PC. Lippincott, Williams & Wilkins, 2009

[25] http://wwwn. cdc. gov/TRAVEL/yellowBookCh4-Malaria.  aspx

[26] Mayton CA. Tetracycline labeling of bone (http://www. histosearch. com/histonet/Dec02/TetracyclinelabelingofbonA.  html)

[27] The Johns Hopkins Medical Institutions. > Tetracycline Labeling (http://pathology2.  jhu. edu/bonelab/4cycline.  htm) Last updated

1/8/2001.

[28] Olson CA, et al. Bait ingestion by free-ranging raccoons and nontarget species in an oral rabies vaccine field trial in Florida (http://www. jwildlifedis. org/cgi/reprint/36/4/734). J Wildl Dis. 2000 Oct;36(4):734-43.

[29] William J. Cromie (February 10, 2000). "Researchers Switch Cancer Off and On -- In Mice" (http://www.  hno.  harvard.  edu/gazette/2000/ 

02.  10/leukemia.  html). . Retrieved 2008-10-25.

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