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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

[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

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
Efficacy of narasin in the prevention of necrotic enteritis in broiler chickens.
2001 Jan-Mar
Reduced incidence of Clostridium perfringens-associated lesions and improved performance in broiler chickens treated with normal intestinal bacteria from adult fowl.
2001 Jan-Mar
Comparison of susceptibility to antimicrobials of the enterococcal species isolated from pigeons (Columba livia).
2002 Fall
Structure, conformation, and mechanism in the membrane transport of alkali metal ions by ionophoric antibiotics.
2002 Feb-Mar
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
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.
2003 Aug
The efficacy of bacitracin methylene disalicylate when fed in combination with narasin in the management of necrotic enteritis in broiler chickens.
2003 Mar
A new method for in vitro detection of microbially produced mitochondrial toxins.
2003 Oct-Dec
Ionophores: their use as ruminant growth promotants and impact on food safety.
2003 Sep
Incidence of residues of nine anticoccidials in eggs.
2005 Nov
An integrated sample preparation to determine coccidiostats and emerging Fusarium-mycotoxins in various poultry tissues with LC-MS/MS.
2007 May
Sensitivity of Eimeria field isolates in the United States: responses of nicarbazin-containing anticoccidials.
2008 Sep
Evaluation of certain veterinary drug residues in food.
2009
Fate and antibacterial potency of anticoccidial drugs and their main abiotic degradation products.
2009 Feb
[Determination of 5 polyether antibiotics in chicken tissues by liquid chromatography-electrospray ionization tandem mass spectrometry].
2009 Nov
The activity and compatibility of the antibiotic tiamulin with other drugs in poultry medicine--A review.
2009 Nov
Determination of veterinary pharmaceuticals in poultry litter and soil by methanol extraction and liquid chromatography-tandem mass spectrometry.
2009 Sep
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
The effect of commonly used anticoccidials and antibiotics in a subclinical necrotic enteritis model.
2010 Feb
Multi-residue method for detecting coccidiostats at carry-over level in feed by HPLC-MS/MS.
2010 Jun
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
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

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 Fri Dec 15 16:10:20 GMT 2023
Edited
by admin
on Fri Dec 15 16:10:20 GMT 2023
Record UNII
DZY9VU539P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NARASIN
GREEN BOOK   INN   MART.   MI   USAN   USP   USP-RS  
INN   USAN  
Official 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
MONTEBAN
Brand Name English
COMPOUND 79891
Code English
Classification Tree Code System Code
CFR 21 CFR 558.363
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
WHO-VATC QP51AH04
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
CFR 21 CFR 556.428
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
WHO-VATC QP51AH54
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
NCI_THESAURUS C258
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
Code System Code Type Description
EVMPD
SUB09163MIG
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PRIMARY
ChEMBL
CHEMBL2104423
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PRIMARY
INN
3935
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PRIMARY
EPA CompTox
DTXSID2046707
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PRIMARY
SMS_ID
100000080340
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PRIMARY
RS_ITEM_NUM
1457458
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PRIMARY
DRUG BANK
DB11432
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PRIMARY
MERCK INDEX
m7771
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
PRIMARY Merck Index
DAILYMED
DZY9VU539P
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
PRIMARY
NCI_THESAURUS
C81445
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PRIMARY
WIKIPEDIA
Narasin
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
PRIMARY
PUBCHEM
65452
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PRIMARY
RXCUI
1314370
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
PRIMARY RxNorm
CAS
55134-13-9
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
PRIMARY
MESH
C013612
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
PRIMARY
FDA UNII
DZY9VU539P
Created by admin on Fri Dec 15 16:10:20 GMT 2023 , Edited by admin on Fri Dec 15 16:10:20 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY