Chlortetracycline

Structural formula
General
Non-proprietary name	Chlortetracycline
other names	7-chloro-4-dimethylamino-1,2,3,4,4a, 5,5a, 6,12,12a-decahydro-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12- trioxo-2-naphthacene carboxamide; Aureomycin;
Molecular formula	C 22 H 23 ClN 2 O 8
Brief description	yellow, odorless, crystalline solid
External identifiers / databases
EC number	200-341-7
ECHA InfoCard	100,000,310
PubChem	5280963
ChemSpider	10469370
DrugBank	DB09093
Wikidata	Q417948
Drug information
ATC code	A01 AB21 ; D06 AA02 ; J01 AA03 ; S01 AA02 ;
Drug class	antibiotic
properties
Molar mass	478.88 g mol −1
solubility	poorly soluble in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	1500 mg kg −1 ( LD 50 , mouse , oral ) ; 134 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlortetracycline , also known as aureomycin , is an antibiotic obtained from Streptomyces aureofaciens . It was the first tetracycline antibiotic to be discovered .

history

Aureomycin was discovered in 1945 by the American botanist Benjamin Minge Duggar (1872–1956) in the Lederle laboratories . Duggar focused his research on microorganisms from the soil. After testing more than 3,500 strains of soil bacteria and mold, he tested a soil sample from the University of Missouri campus in 1945. A golden yellow substance produced by soil bacteria and molds showed antibiotic properties. After extensive testing, he found out that the substance was active against bacilli, staphylococci and streptococci. Duggar called the substance, the structure of which was clarified in 1952, aureomycin, from the Latin word aureus " golden " and the Greek word mykes, for mushroom (although the producer is not a fungus, but a bacterium that forms mycelium).

use

In human medicine , chlortetracycline is only used as an ointment (trade name aureomycin ) for the treatment of inflammatory acne on the face.

In veterinary medicine , chlortetracycline preparations (mostly formulated as chlortetracycline HCl, CAS number 64-72-2) are used in many animal species for the treatment of infections of the respiratory, urogenital and gastrointestinal tracts, due to the possible development of resistance an antibiogram should be made beforehand.

Contraindications

In principle, chlortetracycline has comparable contraindications as tetracycline . In veterinary medicine, oral administration to ruminants and horses is not allowed.

Other Information

As part of a three-year study by the University of Paderborn, chemists used a model experiment to analyze u. a. the path of chlortetracycline in the food chain. It was found that the antibiotics used in animal husbandry are absorbed by crops when the manure is spread over fields and thus get into food. The preparations could still be detected in the liquid manure after 8 months, and detection was also successful in the upper soil layers of the fields fertilized with it. Antibiotics could even be detected in the root and green parts of plants that are ready for harvest. So found z. B. traces of chlorotetracycline in the grain of winter wheat. The head of this project, Manfred Grote, therefore says: “The globally increasing risks from antibiotic resistance can be intensified by the use of pharmaceuticals in agricultural animal husbandry, if antibiotic residues not only get into food from animals but also through crops . "

Trade names

Chlortetracycline is marketed in Germany under the name Aureomycin and in Austria in combination with triamcinolone acetonide under the name Aureocort .

Veterinary preparations are Animedazon Spray , Citrolan CTC , CTC-HCl , Cyclo Spray and Cepemycin (as eye ointment for horses, cattle, dogs and cats).

Individual evidence

↑ ^a ^b ^c D. C. Plumb. In: Veterinary Drug Handbook , Pharma Vet Publishing, White Bear Lake (USA), 1999, p. 853, ISBN 0-8138-2353-6 .
↑ ^a ^b Datasheet Chlortetracycline Selective Supplement from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
↑ ^a ^b Entry on chlortetracycline in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Benjamin Duggar, et al. (1948): Aureomycin, a product of the continuing search for new antibiotics . In: Annals of the New York Academy of Sciences . Vol. 51, pp. 177-181.
↑ Karl Wurm, AM Walter: Infectious Diseases. In: Ludwig Heilmeyer (ed.): Textbook of internal medicine. Springer-Verlag, Berlin / Göttingen / Heidelberg 1955; 2nd edition, ibid. 1961, pp. 9–223, here: p. 50.
↑ Red List , accessed June 13, 2019.
↑ ^a ^b R. Kroker: Pharmaceuticals for the treatment and prevention of bacterial infections , in: Pharmakotherapie bei Haus- und Nutztiere , Parey, Berlin (D), 1999, pp. 211–246, ISBN 3-8263-3286-5 .
^ JE Riviere, JW Spoo: Tetracycline Antibiotics , in: Veterinary Pharmacology and Therapeutics , Iowa State University Press, Ames (USA) 7, 1995, pp. 784-796, ISBN 0-8138-1741-2 .
↑ chemie.de: Chemists at the University of Paderborn prove for the first time that crops absorb antibiotics from manure-fertilized soils , June 9, 2005, accessed on May 14, 2017.
↑ Red List online, as of September 2009.
↑ AGES-PharmMed, as of September 2009.

[DCP-1] D. C. Plumb. In: Veterinary Drug Handbook , Pharma Vet Publishing, White Bear Lake (USA), 1999, p. 853, ISBN 0-8138-2353-6 .

[Sigma-2] Datasheet Chlortetracycline Selective Supplement from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).

[ChemIDplus-3] Entry on chlortetracycline in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] Benjamin Duggar, et al. (1948): Aureomycin, a product of the continuing search for new antibiotics . In: Annals of the New York Academy of Sciences . Vol. 51, pp. 177-181.

[5] Karl Wurm, AM Walter: Infectious Diseases. In: Ludwig Heilmeyer (ed.): Textbook of internal medicine. Springer-Verlag, Berlin / Göttingen / Heidelberg 1955; 2nd edition, ibid. 1961, pp. 9–223, here: p. 50.

[6] Red List , accessed June 13, 2019.

[kroker-7] R. Kroker: Pharmaceuticals for the treatment and prevention of bacterial infections , in: Pharmakotherapie bei Haus- und Nutztiere , Parey, Berlin (D), 1999, pp. 211–246, ISBN 3-8263-3286-5 .

[8] JE Riviere, JW Spoo: Tetracycline Antibiotics , in: Veterinary Pharmacology and Therapeutics , Iowa State University Press, Ames (USA) 7, 1995, pp. 784-796, ISBN 0-8138-1741-2 .

[9] .de: Chemists at the University of Paderborn prove for the first time that crops absorb antibiotics from manure-fertilized soils , June 9, 2005, accessed on May 14, 2017.

[10] Red List online, as of September 2009.

[11] AGES-PharmMed, as of September 2009.