Salinomycin

(2R ) -2 - [ (5S, 6R ) -6 - [( 1S, ​​2S, 3S, 5R) -5 - [( 2S, 5R, 7S, 9S, 10S, 12R, 15R ) -2 - [ (2R, 5R, 6S )-5 -ethyl -5-hydroxy -6-methyl -2 -tetrahydropyranyl ] - 15 -hydroxy-2 ,10,12 -trimethyl -1 ,6,8 - trioxadispiro [ 4.1.5 ^ {7} .3 ^ { 5 }] pentadec -13 -en- 9-yl ]-2 -hydroxy-1 ,3-dimethyl -4- oxoheptyl ] - 5-methyl -2 -tetrahydropyranyl ] -butyric acid (IUPAC)

• C42H70O11 (free acid)
• C42H69O11Na (sodium salt)

• 53003-10-4 (free acid)
• 55721-31-8 (sodium salt)

QP51AH01

• 751.00 g · mol -1 (free acid)
• 772.98 g.mol -1 ( sodium salt)

Risk

• 50 mg · kg -1 ( LD50, Mouse, oral, free acid)
• 18 mg · kg -1 ( LD50, mouse, i.p. free acid)
• 50-148 mg · kg -1 ( LD50, Mouse, oral, sodium salt)

Template: Infobox chemical / molecular formula search available

Salinomycin is a polyether antibiotic produced by Streptomyces albus.

Synthesis and Properties

The macromolecule is a structurally dispiro ketal compound and biosynthesized in the polyketide pathway. The total chemical synthesis was first described in 1998.

Application

Veterinary Medicine

The sodium salt of salinomycin is used as a feed additive (E 766 ) for the prevention of coccidiosis in broiler chickens and rabbits for fattening. Except against coccidia it is effective against certain Gram- positive bacteria, but not against enterobacteria. In the applied concentration of salinomycin for chickens is poisonous to horses and turkeys.

The maximum residue concentration in the EU is in broilers at 5 mcg / kg salinomycin in all wet tissues.

Human Medicine

In human medicine, the use of salinomycin is explored in the treatment of certain cancers, as it cell death (apoptosis ) should result in so-called tumor stem cells.