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N1271

Sigma-Aldrich

Narasin from Streptomyces auriofaciens

≥98% (HPLC)

Synonym(s):

4-methylsalinomycin, Monteban, narasin A

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About This Item

Empirical Formula (Hill Notation):
C43H72O11
CAS Number:
55134-13-9
Molecular Weight:
765.03
MDL number:
MFCD00133653
UNSPSC Code:
51102829
PubChem Substance ID:
24897476
NACRES:
NA.85

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

methanol: soluble 20 mg/mL

antibiotic activity spectrum

Gram-positive bacteria
fungi
viruses

Mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

CCC(C1OC(C(C)CC1C)C(C)C(O)C(C)C(=O)C(CC)C2OC3(OC4(CCC(C)(O4)C5CCC(O)(CC)C(C)O5)C(O)C=C3)C(C)CC2C)C(O)=O

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)

InChI key

VHKXXVVRRDYCIK-UHFFFAOYSA-N

Application

Narasin is a growth-promoting ionophoric antibacterial agent for Enterococci, specifically Enterococcus faecium and Enterococcus faecalis. It inhibits coccidial infection in poultry and mammals and is used in studies involving sodium calcium ion exchange.

Biochem/physiol Actions

Narasin administration in swine results in improved nitrogen digestibility, which decreases fecal nitrogen and increases the relative concentrations of propionic acid in the large intestine. Polyether ionophores, such as Narasin, have a hydrophilic interior and a hydrophobic exterior. The lipophilic ionophore attaches to the lipid rich cell membranes of Gram-positive bacteria. Ionophores bind Na+, K+, and H+ and facilitate their transfer across the bacterial cell membrane, resulting in an increase in H+ concentration on the inside of the Gram-positive cell. Therefore, the H+ ATPase pump is activated to transport out excess H+. The cell is depleted of its energy resources and reduces fermentative functions and cell division .

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mervi Rokka et al.
Food additives and contaminants, 23(5), 470-478 (2006-04-29)
A published confirmatory method for the quantitative determination of four ionophoric coccidiostats (lasalocid, monensin, salinomycin and narasin) in eggs and broiler meat has been further developed. It is proposed for replacement of liquid chromatography methods previously used in analysis of
S B Turnipseed et al.
Journal of AOAC International, 84(3), 640-647 (2001-06-22)
A liquid chromatographic/mass spectrometric (LC/MS) electrospray confirmation method has been developed to confirm 4 ionophores (monensin, lasalocid, salinomycin, and narasin) in a variety of animal feeds using a single quadrupole mass spectrometer. The sodium ions of these compounds are dominant
A J Wuethrich et al.
Journal of animal science, 76(4), 1056-1063 (1998-05-15)
The effect of narasin on apparent nitrogen and dry matter digestibilities and large intestine VFA concentrations in finishing swine was investigated. The study used 21 crossbred barrows averaging 72 kg. Seven blocks were formed on the basis of pretreatment dry
Jean-François Brazeau et al.
Organic letters, 12(1), 36-39 (2009-12-29)
An efficient synthesis of the C1-C17 western unit of narasin was achieved from (S)-Roche ester. Highlights in our synthesis include the successful exploitation of three stereoselective sequences of Lewis acid mediated reaction followed by free-radical-based hydrogen transfer.
Kari Grave et al.
Preventive veterinary medicine, 62(1), 59-72 (2004-05-25)
When avoparcin was prohibited for use as feed additive in poultry in Norway on 31 May 1995, an increased incidence of Clostridium perfringens-associated necrotic enteritis (NE) and an increase in the use of antibacterial (AB) drug therapy in meat-type poultry
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