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N1271

Sigma-Aldrich

Narasin from Streptomyces auriofaciens

≥98% (HPLC)

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Synonym(s):
4-methylsalinomycin, Monteban, narasin A
Empirical Formula (Hill Notation):
C43H72O11
CAS Number:
Molecular Weight:
765.03
MDL number:
UNSPSC Code:
51101500
PubChem Substance ID:
NACRES:
NA.85

Quality Level

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

Related Categories

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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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Tetrahedron Letters, 47, 10109-10109 (1991)
Pekka Peippo et al.
Journal of agricultural and food chemistry, 52(7), 1824-1828 (2004-04-01)
Anticoccidial drugs are extensively used in the poultry industry to control the infection of the single-cell protozoa of the genus Eimeria. The most commonly used coccidiostats in poultry are the polyether ionophores such as narasin and salinomycin. This paper presents
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
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
Mervi Rokka et al.
Molecular nutrition & food research, 49(1), 38-42 (2004-11-13)
Laying hens were fed contaminated feed containing narasin 2.5 mg/kg for 21 days followed by a 7 day withdrawal period, hens in the control group were fed unmedicated feed. Eggs were collected during trial days 0, 3, 7, 14, 21

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