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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
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-
1,11-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
PubChem [12]
CID 643969
DrugBank [13]
DB00759
ChemSpider [14]
10257122
Chemical data
Formula C H NO
22 24 2 8
Mol. mass 444.435 g/mol
Pharmacokinetic data
Therapeutic considerations
[15]
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Mechanism of action
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]
Tetracycline antiporter
system
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.
Indication
It 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
Tetracycline 4
License
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