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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Preventing
Monteban

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Record UNII
DZY9VU539P
Record Status Validated (UNII)
Record Version