Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C43H72O11 |
Molecular Weight | 765.0252 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@](O)(CC)[C@H](C)O1)[C@]2(C)CC[C@]3(O2)O[C@@]4(O[C@]([H])([C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)[C@]5([H])O[C@@]([H])([C@@H](CC)C(O)=O)[C@@H](C)C[C@@H]5C)[C@@H](C)C[C@H]4C)C=C[C@H]3O
InChI
InChIKey=VHKXXVVRRDYCIK-CWCPJSEDSA-N
InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)/t23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,36+,37+,38-,40-,41+,42-,43-/m0/s1
Molecular Formula | C43H72O11 |
Molecular Weight | 765.0252 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.fda.gov/downloads/AnimalVeterinary/DevelopmentApprovalProcess/EnvironmentalAssessments/UCM306251.pdfCurator's Comment: Description was created based on several sources, including http://www.sciencedirect.com/topics/page/Narasin and https://www.drugs.com/pro/monteban.html
Sources: http://www.fda.gov/downloads/AnimalVeterinary/DevelopmentApprovalProcess/EnvironmentalAssessments/UCM306251.pdf
Curator's Comment: Description was created based on several sources, including http://www.sciencedirect.com/topics/page/Narasin and https://www.drugs.com/pro/monteban.html
Narasin is a polyether carboxylic ionophore agent that is authorised in Europe according to Commission Regulation No (EC) 1464/2004 as a coccidiostat for use in chickens for fattening with a maximum content of the active substance in feed of 70 mg/kg and a withdrawal period of one day. Narasin is the active ingredient in Monteban, a premix that is incorporated into chicken feed. Narasin is already approved for continuous oral use as Monteban (NADA 118-980) in chicken feed for the prevention of coccidiosis at doses up to 80 mg narasin/kg feed. Narasin is produced by the fermentation of a strain of Streptomyces aureofaciens.The biological activity of narasin is based on its ability to form lipid soluble and dynamically reversible complexes with cations, preferably monovalent cations such as alkaline K+, Na+ and Rb+: Narasin functions as a carrier of these ions, mediating an electrically neutral exchangediffusion type of ion transport across the membranes. The resultant changes in transmembrane ion gradients and electrical potentials produce critical effects on cellular function and metabolism of coccidia. Narasin is effective against sporozoites and early and late asexual stages of coccidia in broilers caused by Eimeria acervulina, E. brunetti, E. maxima, E. mivati, E. necatrix and E. tenella. Narasin also is used for prevention of necrotic enteritis in broiler chicken. Narasin was identified and characterized as a novel agent that inhibits DENV replication in vitro through non-cytotoxic mechanisms, thus indicating its potential to be further developed as a therapeutic anti-DENV agent.
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/627518
Curator's Comment: The discovery and fermentation of narasin - BOECK, L. D.; M. M. HOEHN, R. E. KASTNER, R. W. WETZEL, N. E. DAVIS & J. E. WESTHEAD: Narasin, a new polyether antibiotic: discovery and fermentation studies. Develop. in Industr. Microbiol. 18: 471- 485, 1977
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL613966 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22155902 |
0.39 µM [IC50] | ||
Target ID: CHEMBL613360 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22155902 |
0.65 µM [IC50] | ||
Target ID: CHEMBL612717 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22155902 |
0.44 µM [IC50] | ||
Target ID: CHEMBL613728 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22155902 |
0.05 µM [IC50] | ||
Target ID: map04210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23615398 |
|||
Target ID: map04064 Sources: http://www.ncbi.nlm.nih.gov/pubmed/20067776 |
3.6 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Preventing | Monteban Approved UseFor the prevention of coccidiosis caused by Eimeria tenella, E. necatrix, E. acervulina, E. maxima, E. mivati , and E. brunetti , for increased rate of weight gain, and for improved feed efficiency in broiler chickens. Launch Date1992 |
PubMed
Title | Date | PubMed |
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Efficacy of narasin in the prevention of necrotic enteritis in broiler chickens. | 2001 Jan-Mar |
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Reduced incidence of Clostridium perfringens-associated lesions and improved performance in broiler chickens treated with normal intestinal bacteria from adult fowl. | 2001 Jan-Mar |
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Comparison of susceptibility to antimicrobials of the enterococcal species isolated from pigeons (Columba livia). | 2002 Fall |
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Structure, conformation, and mechanism in the membrane transport of alkali metal ions by ionophoric antibiotics. | 2002 Feb-Mar |
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The determination of 5 anticoccidial drugs (nicarbazin, lasalocid, monensin, salinomycin and narasin) in animal livers and eggs by liquid chromatography linked with tandem mass spectrometry (LC-MS-MS). | 2002 Jun |
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Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001. | 2003 Aug |
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The efficacy of bacitracin methylene disalicylate when fed in combination with narasin in the management of necrotic enteritis in broiler chickens. | 2003 Mar |
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A new method for in vitro detection of microbially produced mitochondrial toxins. | 2003 Oct-Dec |
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Ionophores: their use as ruminant growth promotants and impact on food safety. | 2003 Sep |
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Incidence of residues of nine anticoccidials in eggs. | 2005 Nov |
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An integrated sample preparation to determine coccidiostats and emerging Fusarium-mycotoxins in various poultry tissues with LC-MS/MS. | 2007 May |
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Sensitivity of Eimeria field isolates in the United States: responses of nicarbazin-containing anticoccidials. | 2008 Sep |
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Evaluation of certain veterinary drug residues in food. | 2009 |
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Fate and antibacterial potency of anticoccidial drugs and their main abiotic degradation products. | 2009 Feb |
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[Determination of 5 polyether antibiotics in chicken tissues by liquid chromatography-electrospray ionization tandem mass spectrometry]. | 2009 Nov |
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The activity and compatibility of the antibiotic tiamulin with other drugs in poultry medicine--A review. | 2009 Nov |
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Determination of veterinary pharmaceuticals in poultry litter and soil by methanol extraction and liquid chromatography-tandem mass spectrometry. | 2009 Sep |
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Simultaneous determination of polyether ionophores, macrolides and lincosamides in hen eggs by liquid chromatography-electrospray ionization tandem mass spectrometry using a simple solvent extraction. | 2010 Dec 3 |
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The effect of commonly used anticoccidials and antibiotics in a subclinical necrotic enteritis model. | 2010 Feb |
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Multi-residue method for detecting coccidiostats at carry-over level in feed by HPLC-MS/MS. | 2010 Jun |
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Interference free detection for small molecules: probing the Mn2+-doped effect and cysteine capped effect on the ZnS nanoparticles for coccidiostats and peptide analysis in SALDI-TOF MS. | 2010 May |
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Direct aqueous supercritical fluid extraction coupled on-line with liquid chromatography-tandem mass spectrometry for the analysis of polyether ionophore antibiotics in water. | 2010 May 14 |
Patents
Sample Use Guides
For the prevention of coccidiosis in broiler chickens - 54-72 grams/ton
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/25500126
Narasin at 2.5 uM concentrations significantly changed cellular metabolism and membrane desintegrity of HepG2 cells
Substance Class |
Chemical
Created
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Record UNII |
DZY9VU539P
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Validated (UNII)
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CFR |
21 CFR 558.363
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QP51AH04
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21 CFR 556.428
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QP51AH54
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NCI_THESAURUS |
C258
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C81445
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Narasin
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55134-13-9
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C013612
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