Milbemycin oxime

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Structural formula
Structure of milbemycin oxime
General
Non-proprietary name Milbemycin oxime
other names
  • (10 E , 14 E , 16 E ) - (1 R , 4 S , 5 ′ S , 6 R , 6 ′ R , 8 R , 13 R , 20 R , 24 S ) -6′-ethyl-24-hydroxy -5 ', 11,13,22-tetramethyl (3,7,19-trioxatetracyclo [15.6.1.1 4,8 .0 20,24 ] -pentacosa-10,14,16,22-tetraene) -6-spiro -2 ′ - (tetrahydropyran) -2,21-dione 21- ( EZ ) -oxime (70%)
  • (10 E , 14 E , 16 E ) - (1 R , 4 S , 5 ′ S , 6 R , 6 ′ R , 8 R , 13 R , 20 R , 24 S ) -24-Hydroxy-5 ′, 6 ′, 11,13,22-pentamethyl- (3,7,19-trioxatetracyclo [15.6.1.1 4,8 .0 20,24 ] pentacosa-10,14,16,22-tetraene) -6-spiro-2 ′ - (tetrahydropyran) -2,21-dione 21- ( EZ ) -oxime (30%)
Molecular formula
  • C 31 H 43 NO 7 (30%)
  • C 32 H 45 NO 7 (70%)
External identifiers / databases
CAS number 129496-10-2
EC number 680-386-0
ECHA InfoCard 100.205.451
PubChem 9575585
Wikidata Q738452
Drug information
ATC code

Q P54AB01

Drug class

Antiparasitic

properties
Molar mass
  • 541.68 g mol −1 (30%)
  • 555.70 g mol −1 (70%)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 302-332-372-410
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Milbemycin oxime is a drug from the group of milbemycins used in veterinary medicine , which is used as a broad spectrum anti-parasitic agent . It is effective against worms ( anthelmintic ), insects ( insecticidal ) and mites ( acaricidal ).

Mechanism of action

Milbemycins, like avermectins, are fermentation products of ray fungi ( Streptomyces spp.) And have a similar mechanism of action, but a significantly longer effectiveness. Milbemycin oxime is obtained from Streptomyces hygroscopicus aureolacrimosus . It increases in invertebrates the membrane permeability of the nerve or the muscle cells for chloride - ions by binding to glutamate -activated chloride channels. This leads to hyperpolarization of the cell membrane and a blockage of the conduction of excitation.

application

The active ingredient is administered orally and only about 5 to 10% is absorbed; the majority is excreted unchanged in the faeces. The absorbed portion is eliminated in the liver via the bile . Milbemycin oxime is well tolerated and can also be used in dogs with the MDR1 defect . Temporary side effects such as rigidity , tremors and ataxia can occur at high doses .

Milbemycin oxime is effective against a wide range of nematodes , it can also be used against heartworms , although the effectiveness is less than that of ivermectin . In addition, it is effective against various mites ( Sarcoptes , Demodex ).

Milbemycin oxime is combined with other active ingredients in the preparations currently available on the market, so that the spectrum of activity is expanded.

Trade names

Combination preparations
  • with praziquantel : Milbactor , Milbemax , Milprazon , Milpro
  • with Lufenuron : Program Plus
  • with praziquantel and lufenuron: Sentinel Spectrum (marketable until September 6, 2008)
  • with Afoxolaner : Nexgard Spectra
  • with Spinosad : Trifexis

Individual evidence

  1. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (6R, 25R) -5-demethoxy-28-deoxy-6, 28-epoxy-5-hydroxyimino-25-ethyl / methylmilbemycin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA ), accessed July 8, 2020.

Web links