Doxycycline
( 4S, 4aR, 5S, 5aR, 6R, 12aS ) - 4 -dimethylamino- 3,5,10,12,12 a- pentahydroxy -6-methyl -1 ,11- dioxo- 1,4,4 a, 5,5 a, 6,11,12 a- octahydrotetracen -2-carboxamide
- C22H24N2O8 (doxycycline )
- C22H24N2O8 · H2O (doxycycline · hydrate)
- C22H24N2O8 · 1/2 C2H6O · 1/2 H2O (doxycycline · · hemiethanolate hemihydrate )
- 564-25-0 ( Doxycycline )
- 17086-28-1 (doxycycline · hydrate)
- 24390-14-5 (doxycycline · · hemiethanolate hemihydrate )
- J01AA02
- A01AB22
Antibiotics ( tetracyclines )
Inhibition of ribosomal protein synthesis
- 444.43 g · mol -1 ( doxycycline)
- 462.45 g · mol -1 ( · doxycycline hydrate)
- 512.94 g · mol -1 (doxycycline · · hemiethanolate hemihydrate )
201 ° C ( carbonization ) (doxycycline · · hemiethanolate hemihydrate )
Slightly soluble in water (0.63 g · l-1 at 25 ° C)
Attention
1870 mg · kg -1 ( LD50, mouse, oral)
Template: Infobox chemical / molecular formula search available
Doxycycline is an antibiotic in the class of tetracyclines. It has a broad spectrum of activity and shows a bacteriostatic activity against gram- positive, gram- negative cell wall and germs. Likewise, it is effective against Plasmodium sp., But shows little tuberculostatic effectiveness. According to its spectrum of action Doxycycline is used to treat respiratory diseases, urogenital tract infections, infections of the gastrointestinal tract, biliary tract infections, acne, rosacea, chlamydial infections, Lyme disease, as well as numerous rare infections such as plague and anthrax. Similarly, doxycycline by the WHO and the German Society for Tropical Medicine and International e V. Health ( DTG) is recommended to prevent malaria, but there are in Germany for this indication no approved finished product.
Mechanism of action
The mechanism of action of doxycycline is based on inhibition of protein biosynthesis. By a reversible blockade of the binding site of the aminoacyl- tRNA to the 30S ribosomal subunit, the elongation of the peptide chain is interrupted and doxycycline effect but primarily bacteriostatic.
Side effects
While you are taking tetracyclines, including doxycycline, photosensitization was observed in some patients. It is produced by sunlight or UV radiation, a pronounced sunburn. Patients who might expose themselves to direct sunlight or UV irradiation should be informed of this typical tetracycline reaction. The treatment should be discontinued at the first sign of skin redness. In addition, acute hypersensitivity reactions with tongue and larynx swelling can occur, leading to shortness of breath and may cause a life-threatening shock.
Rare side effects include inflammation of the mouth and throat, headache, nausea, vomiting, and (not always regress ) loss or alteration of smell and sense of taste. Especially in case of overdose liver and kidney damage may occur. Concomitant intake of milk and dairy products and other calcium - or magnesium-containing food or drug, the absorption of doxycycline from the gastrointestinal tract decrease ( formation of sparingly soluble complexes ) and thus reduce the therapeutic effect. Concomitant intake of alcohol, the drug is degraded more rapidly due to the increased metabolic rate of the liver. An effective concentration is thereby not reached. The drug product subject to medical prescription.
During pregnancy, lactation and in children under 8 years doxycycline is contraindicated, as may occur in fetuses of 4 month and in infants and children up to 8 years by the retention of doxycycline tooth discoloration, tooth enamel damage and a delay of bone growth.
With simultaneous use of oral contraceptives whose action can be canceled.
Trade names
Aknefug Doxy (D), Antodox (D), Atridox (A), Doxakne (D), dotur (A), Doxyclean (CH), Doxyderma (D), DoxyHexal (D), Doxylag (CH), Doxymono (D), Doxysol (CH), Oraycea (D, A) Periostat (A), Rudocyclin (CH), Supracyclin (CH), Tasmacyclin (CH), Vibramycin (A, CH), Vibravenös (A, CH), Zadorin (CH ), various generics (D, A, CH)
Ambrodoxy (D), ambroxol comp. (D)
Centidox, Doxy, HydroDoxx, Pulmodox, Ronaxan, Soludox