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

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
Structure of NARASIN

SMILES

CC[C@H]([C@@H]1O[C@@H]([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@@H](C)C[C@@H]1C)C(O)=O

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

HIDE SMILES / InChI

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

Description
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

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

Targets

Primary TargetPharmacologyConditionPotency
0.39 µM [IC50]
0.65 µM [IC50]
0.44 µM [IC50]
0.05 µM [IC50]
3.6 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Monteban

Approved Use

For 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 Date

1992
PubMed

PubMed

TitleDatePubMed
Simultaneous determination of polyether ionophores, macrolides and lincosamides in hen eggs by liquid chromatography-electrospray ionization tandem mass spectrometry using a simple solvent extraction.
2010-12-03
Multi-residue method for detecting coccidiostats at carry-over level in feed by HPLC-MS/MS.
2010-06
Direct aqueous supercritical fluid extraction coupled on-line with liquid chromatography-tandem mass spectrometry for the analysis of polyether ionophore antibiotics in water.
2010-05-14
Identification of known drugs that act as inhibitors of NF-kappaB signaling and their mechanism of action.
2010-05-01
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.
2010-05
The effect of commonly used anticoccidials and antibiotics in a subclinical necrotic enteritis model.
2010-02
Synthesis of natural products containing spiroketals via intramolecular hydrogen abstraction.
2010-01-07
Stereocontrolled synthesis of C1-C17 fragment of narasin via a free radical-based approach.
2010-01-01
Veterinary pharmaceuticals and antibiotic resistance of Escherichia coli isolates in poultry litter from commercial farms and controlled feeding trials.
2010-01
Environmental contamination by vancomycin resistant enterococci (VRE) in Swedish broiler production.
2009-12-02
Multi-residue confirmatory method for the determination of twelve coccidiostats in chicken liver using liquid chromatography tandem mass spectrometry.
2009-11-13
Validation of a multi-residue liquid chromatography-tandem mass spectrometry confirmatory method for 10 anticoccidials in eggs according to Commission Decision 2002/657/EC.
2009-11-13
[Determination of 5 polyether antibiotics in chicken tissues by liquid chromatography-electrospray ionization tandem mass spectrometry].
2009-11
The activity and compatibility of the antibiotic tiamulin with other drugs in poultry medicine--A review.
2009-11
Determination of veterinary pharmaceuticals in poultry litter and soil by methanol extraction and liquid chromatography-tandem mass spectrometry.
2009-09
Genotype comparison of sorbitol-negative Escherichia coli isolates from healthy broiler chickens from different commercial farms.
2009-07
Fate and antibacterial potency of anticoccidial drugs and their main abiotic degradation products.
2009-02
Evaluation of certain veterinary drug residues in food.
2009
Sensitivity of Eimeria field isolates in the United States: responses of nicarbazin-containing anticoccidials.
2008-09
Determination of ionophore coccidiostats in feedingstuffs by liquid chromatography-tandem mass spectrometry Part I. Application to targeted feed.
2008-08-05
Coccidia-induced mucogenesis promotes the onset of necrotic enteritis by supporting Clostridium perfringens growth.
2008-03-15
Liquid chromatography-electrospray tandem mass spectrometric method for quantification of monensin in plasma and edible tissues of chicken used in pharmacokinetic studies: applying a total error approach.
2007-05-01
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
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
Occurrence of ionophore antibiotics in water and sediments of a mixed-landscape watershed.
2006-07
Simultaneous determination of four coccidiostats in eggs and broiler meat: validation of an LC-MS/MS method.
2006-05
Incidence of residues of nine anticoccidials in eggs.
2005-11
Deposition and depletion of five anticoccidials in eggs.
2005-09-07
Validation of a method for the determination of narasin in the edible tissues of chickens by liquid chromatography.
2005-03-12
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
Liquid chromatographic method to determine narasin in feedingstuffs and premixtures: development, validation, and interlaboratory study.
2005-01-29
The residue levels of narasin in eggs of laying hens fed with unmedicated and medicated feed.
2005-01
Determination of the ionophoric coccidiostats narasin, monensin, lasalocid and salinomycin in eggs by liquid chromatography/tandem mass spectrometry.
2005
Efficient and sensitive detection of residues of nine coccidiostats in egg and muscle by liquid chromatography-electrospray tandem mass spectrometry.
2004-12-25
Prevalence of vancomycin resistant enterococci on poultry farms established after the ban of avoparcin.
2004-12
Development of multiclass methods for drug residues in eggs: silica SPE cleanup and LC-MS/MS analysis of ionophore and macrolide residues.
2004-11-17
Antimicrobial susceptibility of Swedish, Norwegian and Danish isolates of Clostridium perfringens from poultry, and distribution of tetracycline resistance genes.
2004-04-19
Rapid time-resolved fluoroimmunoassay for the screening of narasin and salinomycin residues in poultry and eggs.
2004-04-07
Susceptibility of Clostridium perfringens strains from broiler chickens to antibiotics and anticoccidials.
2004-02
What has happened in norway after the ban of avoparcin? Consumption of antimicrobials by poultry.
2004-01-30
A new method for in vitro detection of microbially produced mitochondrial toxins.
2003-11-06
Ionophores: their use as ruminant growth promotants and impact on food safety.
2003-09
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.
2003-08
The efficacy of bacitracin methylene disalicylate when fed in combination with narasin in the management of necrotic enteritis in broiler chickens.
2003-03
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).
2002-06
Structure, conformation, and mechanism in the membrane transport of alkali metal ions by ionophoric antibiotics.
2002-02-09
Comparison of susceptibility to antimicrobials of the enterococcal species isolated from pigeons (Columba livia).
2002
Efficient and sensitive screening and confirmation of residues of selected polyether ionophore antibiotics in liver and eggs by liquid chromatography-electrospray tandem mass spectrometry.
2001-11
LC/MS confirmation of ionophores in animal feeds.
2001-06-22
Patents

Patents

Sample Use Guides

For the prevention of coccidiosis in broiler chickens - 54-72 grams/ton
Route of Administration: Oral
In Vitro Use Guide
Narasin at 2.5 uM concentrations significantly changed cellular metabolism and membrane desintegrity of HepG2 cells
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:20:50 GMT 2025
Edited
by admin
on Mon Mar 31 18:20:50 GMT 2025
Record UNII
DZY9VU539P
Record Status Validated (UNII)
Record Version
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Name Type Language
NARASIN
GREEN BOOK   INN   MART.   MI   USAN   USP   USP-RS  
INN   USAN  
Official Name English
MONTEBAN
Preferred Name English
COMPD-79891
Code English
NARASIN [USP IMPURITY]
Common Name English
NARASIN [MI]
Common Name English
NARASIN [GREEN BOOK]
Common Name English
C-7819B
Code English
NARASIN A
Common Name English
NARASIN [USP-RS]
Common Name English
NARASIN [USAN]
Common Name English
NARASIN [MART.]
Common Name English
SALINOMYCIN, 4-METHYL-, (4S)-
Common Name English
ANTIBIOTIC A-28086 FACTOR A
Common Name English
narasin [INN]
Common Name English
COMPOUND 79891
Code English
Classification Tree Code System Code
CFR 21 CFR 558.363
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
WHO-VATC QP51AH04
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
CFR 21 CFR 556.428
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
WHO-VATC QP51AH54
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
NCI_THESAURUS C258
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
Code System Code Type Description
EVMPD
SUB09163MIG
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
ChEMBL
CHEMBL2104423
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
INN
3935
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID2046707
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
SMS_ID
100000080340
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
RS_ITEM_NUM
1457458
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
DRUG BANK
DB11432
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
MERCK INDEX
m7771
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY Merck Index
DAILYMED
DZY9VU539P
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
NCI_THESAURUS
C81445
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
WIKIPEDIA
Narasin
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
PUBCHEM
65452
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
RXCUI
1314370
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY RxNorm
CAS
55134-13-9
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
MESH
C013612
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
FDA UNII
DZY9VU539P
Created by admin on Mon Mar 31 18:20:50 GMT 2025 , Edited by admin on Mon Mar 31 18:20:50 GMT 2025
PRIMARY
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