Oxytetracycline

Structural formula
General
Non-proprietary name	Oxytetracycline
other names	2- (Amino-hydroxymethylidene) -4-dimethylamino-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a, 5,5a, 6,12a-hexahydrotetracene-1,3,12- trion ( IUPAC ); Oxytetracycline; Glomycin; Riomitsin;
Molecular formula	C 22 H 24 N 2 O 9
External identifiers / databases
EC number	201-212-8
ECHA InfoCard	100.001.103
PubChem	54675779
DrugBank	DB00595
Wikidata	Q411646
Drug information
ATC code	J01 AA06 , D06 AA03 , G01 AA07 , S01 AA04
Drug class	antibiotic
properties
Molar mass	460.44 g · mol -1
Physical state	firmly
Melting point	183 ° C ( decomposition )
solubility	very bad in water (0.2 g l −1 )
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	4800 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxytetracycline (synonyms oxytetracycline , glomycin and riomitsin , OTC for short ) is an antibiotic from the group of tetracyclines . It is used locally and cutaneously against infections caused by certain bacteria. In human medicine, oxytetracycline is currently only used in eye and skin ointments and a combination preparation in capsule form.

The antibiotic was discovered in 1948 by AC Finlay and his colleagues at Pfizer , who began mass production of the tetracycline made from the actinomyces Streptomyces aureofaciens and Streptomyces rimosus under the trade name Terramycin . The chemical structure was clarified by Robert B. Woodward in 1952. In 1968 Hans Muxfeldt achieved the total synthesis.

chemistry

Oxytetracycline is a metabolic product of the Streptomycete Streptomyces rimosus .

The yellow, crystalline powder is hygroscopic and freely soluble in water . Its taste is bitter. It is only sparingly soluble in alcohol. As an oxytetracycline base, it is only sparingly soluble in water and looks more tan.

pharmacology

Oxytetracycline effected by binding to the 30S subunit of the ribosome an inhibition of protein biosynthesis in bacteria and is characterized bacteriostatic . In high concentrations it is also able to inhibit protein synthesis in mammals.

Oxytetracycline has a similar spectrum of activity as tetracycline and is effective against mycoplasmas , spirochetes , chlamydia , rickettsiae and some gram-positive (e.g. Propionibacterium acnes ) and -negative bacteria, many of which are resistant to the latter.

In bone to OTC can accumulate in the form of calcium phosphate complexes that are not antibiotic activity and may affect bone growth. When deposited in the tooth enamel , it can turn yellow.

Oxytetracycline is distributed in most tissues, but no therapeutic level is reached in the central nervous system. It can pass through the placenta . It is excreted in the urine and feces.

Areas of application

In human medicine, OTC can be used systemically for infections of the airways ( sinusitis , bronchitis ) or as an ointment for wounds and infections of the anterior eye parts and conjunctiva . It is also used topically to treat acne .

In veterinary medicine, OTC is used to treat infectious diseases caused by pathogens sensitive to oxytetracycline and is approved for all farm animals. The application should always be supported by an antibiogram. Main areas of application are in cattle that anaplasmosis in swine pneumonia and acute exacerbations of eperythrozoonosis and sheep of enzootic abortion (Infectious Verlammen). OTC can be used locally for infections of the skin (e.g. clay limb ). In cattle, OTC can be used locally in the form of foam tablets in the uterus for postpartum disorders and as an ointment for udder infections . The antibiotic is also used in drug premixes for pigs.

Contraindications

The product should not be used during pregnancy . In the case of liver and kidney damage, a dose reduction is appropriate.

In the event of an overdose, oxytetracycline is severely damaging to the kidneys and causes kidney failure .

Trade names

Monopreparations

Unguentum Oxytetracyclini SR (D), Spiritus Oxytetracyclini SR (D) and a generic (D)

Combination preparations

Corti Biciron (D), Oxytetracycline-Prednisolon Eye Ointment (D), Tetra-Gelomyrtol (D), Trimovate (D)

Product names in veterinary medicine are Aerocyclin (A), Cuxacyclin , Duphacycline (A), Engemycin (A), Medox , Oxipra , Prophylax (A), Terramycin (A), Tetravit (A), Ursocyclin (A), Vanacyclin (A) as well as various generics (A), OTC blue spray (D)

Web links

Vetpharm entry for Oxytetracycline , accessed November 21, 2011.
Detailed pharmaceutical description for cutaneous use with further information (pdf)
Detailed pharmaceutical description for local application mwN (pdf)

Individual evidence

↑ ^a ^b Oxytetracycline data sheet from Acros, accessed on February 20, 2010.
↑ ^a ^b ^c Datasheet Oxytetra Selective Supplement from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).
↑ 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.

[acros-1] Oxytetracycline data sheet from Acros, accessed on February 20, 2010.

[sigma-2] Datasheet Oxytetra Selective Supplement from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).

[3] 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.