Teicoplanin

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Structural formula
Structural formula of teicoplanin
General
Non-proprietary name Teicoplanin
other names
  • Teichomycin
  • MDL 507
Molecular formula variable
External identifiers / databases
CAS number 61036-62-2
PubChem 16129712
ChemSpider 30844999
DrugBank DB06149
Wikidata Q2731762
Drug information
ATC code

J01 XA02

Drug class

Glycopeptide antibiotics

properties
Molar mass variable
solubility

Easily soluble in water, slightly soluble in dimethylformamide , practically insoluble in ethanol 96%

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
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Teicoplanin is an antibiotic from the group of glycopeptide antibiotics . Its effect is due to the blockade of bacterial cell wall synthesis, this effect is bactericidal. The spectrum of activity mainly includes gram-positive bacteria, including MRSA and Enterococcus faecalis .

Chemically, it is a mixture of glycopeptides produced by certain strains of Actinoplanes teichomyceticus sp. are formed.

Pharmacological properties

The oral bioavailability of teicoplanin is very low, so it must be administered intravenously or intramuscularly for systemic use . When used against Clostridioides difficile in pseudomembranous colitis , oral administration takes place because absorption of the active ingredient is not desired, but the antibiotic effect should be limited to the intestine.

Teicoplanin is not metabolized and is mainly eliminated through the kidneys. The biological half-life is around 150 hours (100 to 170 hours).

Gram-negative bacteria, Chlamydia and Chlamydophila species, Legionella pneumophila and mycoplasmas are naturally resistant .

Chemical properties

Teicoplanin is obtained through fermentation. It is a yellowish, amorphous powder. The six main components are teicoplanin A 2-1 through A 2-5 and teicoplanin A 3-1 . In addition, four secondary components can be clearly identified in the chromatogram: Teicoplanin R S-1 to R S-4 .

Allen Teicoplaninen common is the glycopeptide skeleton (nuclear, germ .: Core ), a Tetra cycle of seven amino acids (five phenylglycine - and two tyrosine derivatives, with a glycosidically bound D-glucosamine and a glycoside mannose (teicoplanin A 3-1 ) ). The other components contain a third glycosidic D-glucosamine component and differ in the N-substitution of the third D-glucosamine residue with different fatty acids .

In pharmaceutical grades, teicoplanin A 2-2 makes up the largest share with 35.0 to 55.0 percent. The teicoplanins are structurally similar to vancomycin .

Main components of teicoplanin
Teicoplanin A 2-1 A 2-2 A 2-3 A 2-4 A 2-5 A 3-1
Side chain fatty acid ( Z ) -4- decanoic acid 8-methylnonanoic acid n-decanoic acid 8-methyldecanoic acid 9-methylnonanoic acid not applicable
CAS number 91032-34-7 91032-26-7 91032-36-9 91032-37-0 91032-38-1 93616-27-4
Molecular formula C 88 H 95 Cl 2 N 9 O 33 C 88 H 97 Cl 2 N 9 O 33 C 88 H 97 Cl 2 N 9 O 33 C 89 H 99 Cl 2 N 9 O 33 C 89 H 99 Cl 2 N 9 O 33 C 72 H 68 Cl 2 N 8 O 28
Molar mass 1878 g cm −3 1880 g cm −3 1880 g cm −3 1894 g cm −3 1894 g cm −3 1564 g cm −3
UNII 36DYU0VKRK 9V7Z6HDK93 6LN24Z7AMM 83Q83MG55O 55234TX04D SR8H9JSC9D
Percentage according to Ph.Eur. Max. 20.0% 1 35.0 to 55.0% Max. 20.0% 2 Max. 20.0% Max. 20.0% 3
At least 80.0% 4 Max. 15.0% 5

1based on the entire A 2-1 group, cf. Chromatogram in the CRS information leaflet
2based on the entire A 2-3 group, cf. Chromatogram in the CRS information leaflet
3based on the entire A 2-5 group, cf. Chromatogram in the CRS information leaflet
4thbased on the entire A 2 group, cf. Chromatogram in the CRS information leaflet
5based on the entire A 3 group, cf. Chromatogram in the CRS information leaflet

use

Teicoplanin is indicated for the parenteral treatment of severe staphylococcal or enterococcal infections , such as complex skin and soft tissue infections, bone and joint infections, nosocomial and community-acquired pneumonia , complicated urinary tract infections, infectious endocarditis and peritonitis .

Teicoplanin is also indicated for oral use as an alternative treatment for diarrhea and colitis caused by infection with Clostridium difficile .

Serious among the side effects is ototoxicity , which occurs in a dose-dependent manner. The occurrence of kidney damage, thrombocytopenia and skin reactions ( Red-man syndrome ) were also observed.

Individual evidence

  1. ↑ a b c d European Pharmacopoeia, 8th edition, Grundwerk 2014, p. 4944 ff.
  2. ↑ a b data sheet Teicoplanin, cont. 80 +% A2 at AlfaAesar, accessed on March 28, 2020 ( PDF )(JavaScript required) .
  3. ↑ a b c d e G. Geisslinger et al .: Mutschler drug effects . 11th edition. WVG, Stuttgart 2019, p. 1003 ff.
  4. ↑ a b c Technical information Targocid 100/200/400 mg (Sanofi-Aventis Deutschland GmbH), as of October 2017.
  5. ↑ a b c d e f Information leaflet - Ph.Eur. Reference Standard - Teicoplanin for identification CRS batch 2 . January 7, 2020 ( PDF )
  6. ↑ A. Bernareggi et. al: Teicoplanin metabolism in humans. Antimicrobial Agents Chemotherapy, Volume 36 (1992), pp 1744-1749. PMC 192040 (free full text). doi : 10.1128 / AAC.36.8.1744
  7. ↑ a b Theo Dingermann , Karl Hiller, Georg Schneider, Ilse Zündorf: Schneider drug drugs. 5th edition. Elsevier, Munich 2004, p. 566 f. ISBN 3-8274-1481-4 .