Salinomycin

Structural formula
General
Non-proprietary name	Salinomycin
other names	(2 R ) -2 - [(5 S , 6 R ) -6 - [(1 S , 2 S , 3 S , 5 R ) -5 - [(2 S , 5 R , 7 S , 9 S , 10 S , 12 R , 15 R ) -2 - [(2 R , 5 R , 6 S ) -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 )
Molecular formula	C 42 H 70 O 11 (free acid) ; C 42 H 69 O 11 Na (sodium salt) ;
External identifiers / databases
EC number	258-290-1
ECHA InfoCard	100.052.974
PubChem	72370
ChemSpider	2342058
Wikidata	Q411909
Drug information
ATC code	Q P51AH01
properties
Molar mass	751.00 g · mol -1 (free acid) ; 772.98 g mol −1 (sodium salt) ;
Melting point	112.5–113.5 ° C (free acid) ; 140–142 ° C (sodium salt) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 300
	P: 264-301 + 310
Toxicological data	50 mg kg −1 ( LD 50 , mouse , oral , free acid) ; 18 mg kg −1 ( LD 50 , mouse , ip , free acid) ; 50–148 mg kg −1 ( LD 50 , mouse , oral , sodium salt) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Salinomycin is a polyether - antibiotic and is used by Streptomyces albus formed.

Synthesis and properties

The macromolecule is structurally a dispiro - ketal compound and is biosynthesized using the polyketide route . Total chemical synthesis was first described in 1998.

application

Veterinary medicine

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

The maximum permissible residue concentration in the EU for broilers is 5 μg / kg salinomycin in all moist tissues.

Human medicine

In human medicine, the use of salinomycin in the treatment of certain cancers is being researched, as it is believed to lead to cell death ( apoptosis ) in so-called tumor stem cells .

Web links

Entry on salinomycin at Vetpharm, accessed July 30, 2012.
A. Huczyński: Polyether ionophores — promising bioactive molecules for cancer therapy. In: Bioorganic & Medicinal Chemistry Letters. 22, 2012, pp. 7002-7010, doi : 10.1016 / j.bmcl.2012.09.046 .
C. Naujokat, R. Steinhart: Salinomycin as a Drug for Targeting Human Cancer Stem Cells

Individual evidence

↑ ^a ^b ^c ^d data sheet salinomycin from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

↑ ^a ^b ^c Entry on salinomycin. In: Römpp Online . Georg Thieme Verlag, accessed on May 1, 2014.

↑ J. Chem. Soc. , Perkin Trans. 1 1998, 9-40.

↑ Regulation (EC) No. 500/2007 (PDF) of the Commission of 7 May 2007 amending Regulation (EC) No. 1463/2004 with regard to the introduction of a maximum residue level for the animal feed additive Sacox, which belongs to the group “Coccidiostats and other medicinal products” 120 microgranulate.

^ Gupta et al .: PB Identification of Selective Inhibitors of Cancer Stem Cells by High-Throughput Screening. Cell , Vol. 138 (4), 645-659, August 13, 2009. doi : 10.1016 / j.cell.2009.06.034 .

↑ Breast cancer: For the first time active ingredient against tumor stem cells ( Memento of the original from November 23, 2010 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. . In: Deutsches Ärzteblatt, August 14, 2009. @1@ 2

↑ Der Spiegel Online: Animal antibiotic drives cancer cells to suicide. October 14, 2009

↑ Der Spiegel Online: Researchers are testing a new active ingredient against cancer. April 13, 2010.

^ Cord Naujokat, Dominik Fuchs, Gerhard Opelz: "Salinomycin in cancer: A new mission for an old agent". In: Molecular Medicine Reports 3 (4): 555-559, 2010.

↑ A. Huczynski: Salinomycin - a New Cancer Drug Candidate . In: Chemical Biology & Drug Design (2012), 79, 235-238 doi : 10.1111 / j.1747-0285.2011.01287.x .

[Sigma-1] ta sheet salinomycin from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

[Roempp-2] Entry on salinomycin. In: Römpp Online . Georg Thieme Verlag, accessed on May 1, 2014.

[3] J. Chem. Soc. , Perkin Trans. 1 1998, 9-40.

[4] Regulation (EC) No. 500/2007 (PDF) of the Commission of 7 May 2007 amending Regulation (EC) No. 1463/2004 with regard to the introduction of a maximum residue level for the animal feed additive Sacox, which belongs to the group “Coccidiostats and other medicinal products” 120 microgranulate.

[5] Gupta et al .: PB Identification of Selective Inhibitors of Cancer Stem Cells by High-Throughput Screening. Cell , Vol. 138 (4), 645-659, August 13, 2009. doi : 10.1016 / j.cell.2009.06.034 .