U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C42H70O11
Molecular Weight 750.9986
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SALINOMYCIN

SMILES

CC[C@H]([C@H]1CC[C@H](C)[C@@H](O1)[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@H]2O[C@@]3(O[C@@]4(CC[C@](C)(O4)[C@H]5CC[C@](O)(CC)[C@H](C)O5)[C@H](O)C=C3)[C@H](C)C[C@@H]2C)C(O)=O

InChI

InChIKey=KQXDHUJYNAXLNZ-XQSDOZFQSA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C42H70O11
Molecular Weight 750.9986
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23517602 | http://www.merck-animal-health-usa.com/binaries/intp1069_SACOX_tcm96-86731.pdf

Salinomycin as a promising anticancer drug candidate exerts anti-angiogenic and anti-tumorigenic activities by inhibiting vascular endothelial growth factor receptor 2-mediated angiogenesis. Its salt, salinomycin sodium, is an ionophore anticoccidial for use in chickens to prevent coccidiosis caused by Eimeria tenella, E.necatrix, E.acervulina, E.maxima, E.brunetti and E.mivati.

Originator

Sources: JP47025392

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Sacox

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Trypanocidal activity of salinomycin is due to sodium influx followed by cell swelling.
2013-03-21
Fast liquid chromatography/multiple-stage mass spectrometry of coccidiostats.
2009-05
Disruption of a mitochondrial MutS DNA repair enzyme homologue confers drug resistance in the parasite Toxoplasma gondii.
2009-04
Dietary supplementation of mannan-oligosaccharide enhances neonatal immune responses in chickens during natural exposure to Eimeria spp.
2009-03-19
Synergistic fungicidal activities of polymyxin B and ionophores, and their dependence on direct disruptive action of polymyxin B on fungal vacuole.
2009-02
Fate and antibacterial potency of anticoccidial drugs and their main abiotic degradation products.
2009-02
Role of sgcR3 in positive regulation of enediyne antibiotic C-1027 production of Streptomyces globisporus C-1027.
2009-01-22
Effects of salinomycin on cell-mediated immunity of broiler chickens against hydropericardium syndrome and Newcastle disease viruses.
2009-01
Occurrence and elimination of antibiotics at four sewage treatment plants in Japan and their effects on bacterial ammonia oxidation.
2009
Compatibility of a combination of tiamulin and chlortetracycline with salinomycin in feed during a pulsed medication program coadministration in broilers.
2008-12
Investigation of chicken intestinal bacterial communities by 16S rRNA targeted fluorescence in situ hybridization.
2008-10
Determination of ionophore coccidiostats in feedingstuffs by liquid chromatography-tandem mass spectrometry Part I. Application to targeted feed.
2008-08-05
Compatibility of a combination of tiamulin plus chlortetracycline with salinomycin in feed during a long-term co-administration in broilers.
2008-08
Natural Products and Medicinal Chemistry--the 22nd Mona Symposium.
2008-03
Pharmacological evaluation of contractile activity of the dog heartworm Dirofilaria immitis.
2008-03
Characterization of Streptomyces spp. isolated from the sea surface microlayer in the Trondheim Fjord, Norway.
2008
Conformation and location of membrane-bound salinomycin-sodium complex deduced from NMR in isotropic bicelles.
2007-12-05
Impact of salinomycin on the intestinal microflora of broiler chickens.
2007-10-26
Effects of polyether ionophores on the protective immune responses of broiler chickens against Angara disease and Newcastle disease viruses.
2007-10
Liquid chromatography-tandem mass spectrometric assays for salinomycin in mouse plasma, liver, brain and small intestinal contents and in OptiMEM cell culture medium.
2007-08-15
Salinomycin toxicosis in horses.
2007-06-15
Microarchitecture and spatial relationship between bacteria and ileal, cecal, and colonic epithelium in chicks fed a direct-fed microbial, PrimaLac, and salinomycin.
2007-06
Direct-fed microbial PrimaLac and salinomycin modulate whole-body and intestinal oxygen consumption and intestinal mucosal cytokine production in the broiler chick.
2007-06
An integrated sample preparation to determine coccidiostats and emerging Fusarium-mycotoxins in various poultry tissues with LC-MS/MS.
2007-05
Efficacy of some anticoccidial drugs for treating coccidial enteritis of the common carp caused by Goussia carpelli (Apicomplexa: Eimeriidae).
2007-03
Evaluation of the efficacy of a probiotic containing Lactobacillus, Bifidobacterium, Enterococcus, and Pediococcus strains in promoting broiler performance and modulating cecal microflora composition and metabolic activities.
2007-02
Multiple regulatory genes in the salinomycin biosynthetic gene cluster of Streptomyces albus CCM 4719.
2007
Prevalence and antimicrobial resistance of enterococci isolated from retail fruits, vegetables, and meats.
2006-12
Combined effect of salinomycin and feeding on whole body glucose kinetics in sheep fed a high-concentrate diet.
2006-11-17
Determination of monensin, narasin, and salinomycin in mineral premixes, supplements, and animal feeds by liquid chromatography and post-column derivatization: collaborative study.
2006-10-18
Persistence of antibiotics such as macrolides, tiamulin and salinomycin in soil.
2006-10
Increased level of Eimeria sensitivity to diclazuril after using a live coccidial vaccine.
2006-09
Microbial community composition of the ileum and cecum of broiler chickens as revealed by molecular and culture-based techniques.
2006-07
Occurrence of ionophore antibiotics in water and sediments of a mixed-landscape watershed.
2006-07
Elimination of macrolides, tiamulin, and salinomycin during manure storage.
2006-07
[The effect of betain on biology and morphology of developmental stages of Eimeria acervulina in broiler chicks experimentally infected].
2006-06-20
Effect of dietary zinc level on serum carotenoid levels, body and shank pigmentation of chickens after experimental infection with coccidia.
2006-06
Evaluation of a Bacillus stearothermophilus tube test as a screening tool for anticoccidial residues in poultry.
2006-06
Simultaneous determination of four coccidiostats in eggs and broiler meat: validation of an LC-MS/MS method.
2006-05
A case of salinomycin intoxication in turkeys.
2006-03
Stereoselective synthesis of the western hemisphere of salinomycin.
2006-02-02
Tiamulin resistance in porcine Brachyspira pilosicoli isolates.
2006-02
Antiparasitic and immunomodulatory effect of innovative treatments against Myxobolus sp. infection in Diplodus puntazzo.
2005-12-10
Incidence of residues of nine anticoccidials in eggs.
2005-11
HPLC determination of salinomycin and related compounds in fermentation media of Streptomyces albus and premixes.
2005-09-15
Effects of Natustat supplementation on performance, feed efficiency and intestinal lesion scores in broiler chickens challenged with Eimeria acervulina, Eimeria maxima and Eimeria tenella.
2005-06-30
Rapid analysis of trace levels of antibiotic polyether ionophores in surface water by solid-phase extraction and liquid chromatography with ion trap tandem mass spectrometric detection.
2005-02-18
Performance and nutrient retention responses of broilers to dietary oxyhalogenic and ionic salts.
2005-02
Radical oxidative cyclization of spiroacetals to bis-spiroacetals: an overview.
2004-05-31
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.
2003-08
Patents

Sample Use Guides

Salinomycin Sodium is approved for use at 40 - 60 grams per ton of medicated feed.
Route of Administration: Oral
The trypanocidal activity of salinomycin was determined with bloodstream forms of the T. brucei clone 427–221 while the general cytotoxicity of the ionophore was evaluated with human HL-60 cells and normal PBMCs (peripheral blood mononuclear cells). Cells were seeded in 24-well plates in a final volume of 1 ml of appropriate culture medium (trypanosomes: Baltz medium; human cells: RPMI medium) supplemented with 16.7% (v/v) heat-inactivated foetal bovine serum and containing various concentrations of salinomycin (10-4 to 10-9 M) and 1% DMSO. Wells containing medium and 1% DMSO served as controls. The initial cell densities were 1 × 104/ml for trypanosomes, 1 × 105/ml for HL-60 cells and 5 × 105/ml for PBMCs. After 24 h incubation, 100 μl of a 0.44 mM resazurin solution prepared in PBS was added and the cells were incubated for a further 48 h. Thereafter, the plates were read on a microplate reader using a test wavelength of 570 nm and a reference wavelength of 630 nm. The 50% growth inhibition (GI50) value (trypanosomes and HL-60 cells) and the 50% effective concentration (EC50) value (PBMCs), i.e., the concentration of salinomycin necessary to reduce the growth rate of cells by 50% or to cause an effect in 50% of cells compared to the control, were determined from mean values using the 4-parameter logistic model
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:25:25 GMT 2025
Edited
by admin
on Mon Mar 31 18:25:25 GMT 2025
Record UNII
62UXS86T64
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROCOXACIN
Preferred Name English
SALINOMYCIN
HSDB   INN   MI  
INN  
Official Name English
salinomycin [INN]
Common Name English
SALINOMYCIN [MI]
Common Name English
SALINOMYCIN [JAN]
Common Name English
SALINOMYCIN [HSDB]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 862721
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
CFR 21 CFR 556.592
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
FDA ORPHAN DRUG 713219
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
WHO-VATC QP51AH01
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
NCI_THESAURUS C258
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
CFR 21 CFR 558.550
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
Code System Code Type Description
EVMPD
SUB10428MIG
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
MESH
C010327
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
SMS_ID
100000080526
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
CAS
53003-10-4
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
NCI_THESAURUS
C76430
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
INN
4256
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
RXCUI
1311566
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
258-290-1
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
PUBCHEM
3085092
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
DRUG BANK
DB11544
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
WIKIPEDIA
SALINOMYCIN
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
MERCK INDEX
m9743
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID4048486
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
DAILYMED
62UXS86T64
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
ChEMBL
CHEMBL1208572
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
FDA UNII
62UXS86T64
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
HSDB
7032
Created by admin on Mon Mar 31 18:25:25 GMT 2025 , Edited by admin on Mon Mar 31 18:25:25 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY