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	{{chembox		{{chembox
			| Verifiedfields = changed
	|ImageFile=Salinomycin.png
			| Watchedfields = changed
	|ImageSize=200px
			| verifiedrevid = 373936925
	|IUPACName=(2R)-2--15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiropentadec-13-en-9-yl]-2-hydroxy-1,3-dimethyl-4-oxoheptyl]-5-methyl-2-tetrahydropyranyl]butanoic acid
			| ImageFile=Salinomycin.png
	| IUPACName_hidden = yes
			| IUPACName=(2''R'')-2--15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiropentadec-13-en-9-yl]-2-hydroxy-1,3-dimethyl-4-oxoheptyl]-5-methyl-2-tetrahydropyranyl]butanoic acid
	|OtherNames=
			| OtherNames=
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
			| UNII_Ref = {{fdacite|changed|FDA}}
	| CASNo=53003-10-4
			| UNII = 62UXS86T64
	| PubChem=72370
			| CASNo_Ref = {{cascite|correct|??}}
	| ATCvet = yes
			| CASNo=53003-10-4
	| ATCCode_prefix = P51
			| PubChem=72370
	| ATCCode_suffix = AH01
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| SMILES=O=C((((3()O((CC)C(O)=O)()CC3C)C)O)C)(CC)((C)C2C)()O12O4(CC(5()O(C)(CC)(O)CC5)(C)O4)(O)C=C1 }}
			| ChEMBL = 1208572
			| SMILES = O=C((((3()O((CC)C(O)=O)()CC3C)C)O)C)(CC)((C)C2C)()O12O4(CC(5()O(C)(CC)(O)CC5)(C)O4)(O)C=C1
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 2342058
			| InChI = 1/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1
			| InChIKey = KQXDHUJYNAXLNZ-XQSDOZFQBR
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = KQXDHUJYNAXLNZ-XQSDOZFQSA-N
			}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>42</sub>H<sub>70</sub>O<sub>11</sub>		| C=42 | H=70 | O=11
			| Appearance=
	| MolarMass=751.00 g/mol
	| Appearance=		| Density=
	| Density=		| MeltingPt=
	| MeltingPt=		| BoilingPt=
	| BoilingPt=		| Solubility=
	| Solubility=
	}}		}}
	|Section3={{Chembox Hazards		|Section6={{Chembox Pharmacology
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			|Section7={{Chembox Hazards
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	}}		}}
	}}		}}
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	'''Salinomycin''' is an ] and ] ] therapeutic drug.		'''Salinomycin''' is an ] and ] ] therapeutic drug.
	== Use in cancer ==		== Antibacterial activity ==
			Salinomycin and its derivatives exhibit high antimicrobial activity against ], including the most problematic bacteria strains such as ] and ], and '']''. Salinomycin is inactive against fungi such as ] and ].
	Salinomycin has been shown by Piyush Gupta et al. of the ] and the ] to kill ] stem cells at least 100 times more effectively than another popular anti-cancer drug (]) in mice. The study screened 16 000 different chemical compounds and found that only a small subset, including salinomycin and ], targeted ] responsible for metastasis and relapse.<ref name="newscientist-dn17610">
			<ref>
			{{cite journal
			| author = M. Antoszczak| year = 2014
			| volume =19
			| issue = 12
			| pages= 19435–19459
			| title = Synthesis, Anticancer and Antibacterial Activity of Salinomycin N-Benzyl Amides
			| journal = ]
			| doi = 10.3390/molecules191219435
			| pmid = 25429565
			| pmc = 6271077
			| display-authors=etal| doi-access = free
			}}</ref>
			== Cancer research ==
			===Pre-clinical===
	{{cite news
			Salinomycin has been shown by Piyush Gupta et al. of the ] and the ] to kill ] ]s in mice at least 100 times more effectively than the anti-cancer drug ]. The study screened 16,000 different chemical compounds and found that only a small subset, including salinomycin and ], targeted ] responsible for metastasis and relapse.<ref>{{cite news
	|title=Drug shows cancer stem cells not invulnerable
			| title=Drug shows cancer stem cells not invulnerable
	|publisher=]
			| publisher=]
	|url=http://www.newscientist.com/article/dn17610-drug-shows-cancer-stem-cells-not-invulnerable.html
			| url=https://www.newscientist.com/article/dn17610-drug-shows-cancer-stem-cells-not-invulnerable.html
	|date=2009-08-13}}</ref><ref>{{cite news
			| date=2009-08-13}}
			</ref><ref>
			{{cite news
	| url=http://www.broadinstitute.org/news/1305		| url=http://www.broadinstitute.org/news/1305
	| title=New method takes aim at aggressive cancer cells		| title=New method takes aim at aggressive cancer cells
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	| work=Broad Communications		| work=Broad Communications
	| date=2009-08-13		| date=2009-08-13
	| accessdate=2009-08-13		| access-date=2009-08-13
			}}
	}}</ref><ref>{{cite journal
			</ref><ref>
			{{cite journal
	| doi=10.1016/j.cell.2009.06.034		| doi=10.1016/j.cell.2009.06.034
	| last=Gupta		| last1=Gupta
	| first=P. et al.		| first1=P.
	| pmid=19682730		| pmid=19682730
			| pmc=4892125
	| title=Identification of selective inhibitors of cancer stem cells by high-throughput screening		| title=Identification of selective inhibitors of cancer stem cells by high-throughput screening
	| journal=Cell		| journal=]
	| date=2009-08-13		| date=2009-08-13
	| accessdate=2009-08-13
	| last2=Onder		| last2=Onder
	| first2=Tamer T.		| first2=Tamer T.
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	| volume=138		| volume=138
	| issue=4		| issue=4
	| pages=645		| pages=645–59
			|display-authors=etal}}
	}}</ref>
			</ref><ref>
	The mechanism of action by which Salinomycin kills cancer stem cells specifically remains unknown, but is thought to be due to its action as a potassium ionophore due to the detection of ] in the same compound screen. Salinomycin has high toxicity and a narrow therapeutic window which may limit its clinical use.
			{{cite journal
			| author = Adam Huczynski
			| year = 2012
			| volume =79
			| issue = 3
			| pages=235–238
			| title = Salinomycin – a New Cancer Drug Candidate
			| journal = ]
			| doi = 10.1111/j.1747-0285.2011.01287.x
			| pmid = 22145602
			| s2cid = 40843415
			}}
			</ref>
			The ] by which salinomycin kills cancer stem cells involves lysosomal iron sequestration, leading to the production of reactive oxygen species, lysosome membrane permeabilization and ferroptosis.<ref>{{cite journal |last1=Mai |first1=Trang Thi |last2=Hamaï |first2=Ahmed |last3=Hienzsch |first3=Antje |last4=Cañeque |first4=Tatiana |last5=Müller |first5=Sebastian |last6=Wicinski |first6=Julien |last7=Cabaud |first7=Olivier |last8=Leroy |first8=Christine |last9=David |first9=Amandine |last10=Acevedo |first10=Verónica |last11=Ryo |first11=Akihide |last12=Ginestier |first12=Christophe |last13=Birnbaum |first13=Daniel |last14=Charafe-Jauffret |first14=Emmanuelle |last15=Codogno |first15=Patrice |last16=Mehrpour |first16=Maryam |last17=xRodriguez |first17=Raphaël Rodriguez |title=Salinomycin kills cancer stem cells by sequestering iron in lysosomes |journal=Nature Chemistry |date=Oct 2017 |volume=9 |issue=10 |pages=1025–1033 |doi=10.1038/nchem.2778 |pmid=28937680 |pmc=5890907 |bibcode=2017NatCh...9.1025M }}</ref> Studies performed in 2011 showed that salinomycin could induce ] of human cancer cells at higher concentrations. C20 amino derivatives such as ] have shown to be more potent in vitro models of ] cancer cells and in vivo {{doi| 10.1038/nchem.2778}}. Promising results from a few clinical pilot studies reveal that salinomycin is able to effectively eliminate cancer stem cells and to induce partial clinical regression of heavily pretreated and therapy-resistant cancers. The ability of salinomycin to kill both cancer stem cells and therapy-resistant cancer cells (persister) may define the compound as a novel and an effective anticancer drug.<ref>C. Naujokat, R. Steinhart "Salinomycin as a Drug for Targeting Human Cancer Stem Cells”, '']'', Volume 2012 (2012), Article ID 950658, {{doi| 10.1155/2012/950658}}, </ref><ref>A. Huczyński, ”Polyether ionophores—promising bioactive molecules for cancer therapy”, '']'', 2012,22, 7002-7010,{{doi|10.1016/j.bmcl.2012.09.046}}, </ref> It has been also shown that salinomycin and its derivatives exhibit potent antiproliferative activity against the drug-resistant cancer cell lines.<ref>A. Huczyński, J. Janczak, M. Antoszczak, J. Wietrzyk, E. Maj, B. Brzezinski, ” Antiproliferative activity of salinomycin and its derivatives”, '']'', 2012, 22, 7146-7150,{{doi|10.1016/j.bmcl.2012.09.068}},</ref><ref>
			{{cite journal
			| first1 = Michal | last1 = Antoszczak | first2 = Adam | last2 = Huczynski
			| year = 2015
			| volume =15
			| issue = 5
			| pages= 575–591
			| title = Anticancer Activity of Polyether Ionophore-Salinomycin
			| journal = ]
			| doi = 10.2174/1871520615666150101130209
			| pmid = 25553435 }}
			</ref> Salinomycin is the key compound in the pharmaceutical company Verastem's efforts to produce an anti-cancer-stem-cell drug.{{cn|date=December 2022}}
	== Use in agriculture ==		== Use in agriculture ==
	Salinomycin is used in chicken fodder as a ].		Salinomycin is used in chicken feed as a ].{{cn|date=December 2022}}
	== References ==		== Biosynthesis ==
			A team from the ] has cloned and sequenced the biosynthetic cluster responsible for salinomycin production, from '']'' DSM 41398.<ref>{{cite journal
	{{reflist}}
			| doi=10.1002/cbic.201100590
			| last1=Yurkovich
			| first1=Marie E.
			| pmid= 22076845
			| title=A Late-Stage Intermediate in Salinomycin Biosynthesis Is Revealed by Specific Mutation in the Biosynthetic Gene Cluster
			| journal=]
			| date=2011-11-11
			| last2=Tyrakis
			| first2=Petros A.
			| last3=Hong
			| first3=Hui
			| last4=Sun
			| first4=Yuhui
			| last5=Samborskyy
			| first5=Markiyan
			| last6=Kamiya
			| first6=Kohei
			| last7=Leadlay
			| first7=Peter F.
			| volume=13
			| issue=1
			| pages=66–71
			| s2cid=22332727
			|display-authors=etal}}</ref> This has shown that the ] backbone of salinomycin is synthesised on an assembly line of nine ]) multienzymes. Furthermore, the cluster contains genes involved in oxidative cyclization including ''salC'' (epoxidase) and ''salBI/BII/BIII'' (epoxide hydrolase) genes. The cluster also contains genes suspected to be involved in self-resistance, export, precursor supply and regulation. The cluster contains a NRPS{{clarify|reason=What is NRPS?|date=June 2018}}-like carrier protein, SalX, that is suspected to tether “pre-salinomycin” during oxidative cyclization. By inactivating salC the researchers have demonstrated that salinomycin biosynthesis proceeds via a diene intermediate.{{cn|date=December 2022}}
	==See also==		==See also==
			* ] a derivative of salinomycin which has an additional methyl group.
	* ]
	* ]		* ]
			==References==
			{{Reflist}}
	]		]
	]		]
			]
	]		]
	]		]
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	]		]
	]		]
			]
			]
	]
	]
	]
	]