Tiamulin

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Structural formula
Structural formula of tiamulin
General
Non-proprietary name Tiamulin
other names
  • (3a S , 4 R , 5 S , 6 S , 8 R , 9 R , 9a R , 10 R ) - [2- (Diethylamino) ethylthio] acetic acid-5-hydroxy-4,6,9,10-tetramethyl- 1-oxo-6-vinyl-3a, 9-propanoperhydrocyclopentacycloocten-8-yl ester ( IUPAC )
  • [(3a S , 4 R , 5 S , 6 S , 8 R , 9 R , 9a R , 10 R ) -6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a , 9-propano-3a H -cyclopentacycloocten-8-yl] [[2- (diethylamino) ethyl] sulfanyl] acetate
Molecular formula C 28 H 47 NO 4 S
Brief description

Sticky, translucent, yellowish, slightly hygroscopic mass

External identifiers / databases
CAS number 55297-95-5
EC number 259-580-0
ECHA InfoCard 100.054.145
PubChem 656958
ChemSpider 571196
DrugBank DB11468
Wikidata Q7800111
Drug information
ATC code

Q J01XQ01

Drug class

antibiotic

Mechanism of action

Elongation phase inhibition

properties
Molar mass 493.74 g · mol -1
solubility

Practically insoluble in water, very easily soluble in dichloromethane , easily soluble in anhydrous ethanol

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: 413
P: no P-phrases
Toxicological data

2230 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 .

Tiamulin is an antibiotic active substance from the group of pleuromutilins . It is approved in veterinary medicine for the treatment of certain infectious diseases in pigs ( pig dysentery , porcine proliferative enteritis , porcine colonic spirochaetosis and enzootic pneumonia ) and for the treatment of mycoplasmosis in poultry in turkeys and chickens.

properties

Tiamulin is a semi-synthetically produced substance. Medicinally it is administered as tiamulin hydrogen fumarate with the feed or the drinking water. Intramuscular administration is also possible in pigs , whereby the free base is used.

Tiamulin is an antibiotic belonging to the pleuromutiline group. This group of natural substances originating from mushrooms ( Clitopilus passeckerianus , "cat ear rasp ") was discovered in the 1950s. Besides tiamulin, valnemulin , which is also used in veterinary medicine, and lefamulin and retapamulin, which are used in human medicine, are derived from the lead substance pleuromutilin .

The effect is based on an inhibition of bacterial protein synthesis in that tiamulin binds primarily to the 50S subunit of the ribosomes and possibly also to the joint site of the 50S and 30S subunits.

Spectrum of activity

Tiamulin shows a relatively broad spectrum of activity in vitro . The sensitive germs include porcine and avian mycoplasmas as well as gram-negative anaerobes ( Brachyspira hyodysenteriae , Brachyspira pilosicoli ), gram-negative aerobes ( Actinobacillus pleuropneumoniae , Pasteurella multocida ) and the obligate intracellular lawsonia .

Trade names

Denagard (D), Stalimox (D), Tialin (D), Tyawalt (D), Ursomutin (D), Vetmulin (D)

Individual evidence

  1. ↑ a b European Pharmacopoeia, 8th edition, basic work 2014, “Tiamulin für Tiere”, p. 5035 f.
  2. ↑ a b c Tiamulin data sheet , VETRANAL at Sigma-Aldrich , accessed on November 5, 2019 ( PDF ).
  3. ↑ External identifiers or database links for tiamulin hydrogen fumarate: CAS number: 55297-96-6, EC number: 259-581-6, ECHA InfoCard: 100.054.146 , PubChem : 23725049 , ChemSpider : 27524460 , Wikidata : Q72509073 .
  4. ↑ White to light yellow, crystalline powder, soluble in water, slightly soluble in anhydrous ethanol, soluble in methanol (European Pharmacopoeia, 8th edition, Grundwerk 2014, "Tiamulinhydrogenfumarat für Tiere", p. 5038 f.)
  5. ↑ a b Tiamutin - Article 34 Referral - Annex I, II, III of March 14, 2011 (PDF), 393 KB. See also: European Article 34 risk assessment procedures for Tiamutin (English)