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Nitroxinil

VETRANAL®, analytical standard

Synonym(s):

4-Hydroxy-3-iodo-5-nitrobenzonitrile, Nitroxynil

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About This Item

Empirical Formula (Hill Notation):
C7H3IN2O3
CAS Number:
1689-89-0
Molecular Weight:
290.01
EC Number:
216-884-8
MDL number:
MFCD00070776
UNSPSC Code:
41116107
PubChem Substance ID:
329754805
NACRES:
NA.24

grade

analytical standard

Quality Level

100

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

SMILES string

Oc1c(I)cc(cc1[N+]([O-])=O)C#N

InChI

1S/C7H3IN2O3/c8-5-1-4(3-9)2-6(7(5)11)10(12)13/h1-2,11H

InChI key

SGKGVABHDAQAJO-UHFFFAOYSA-N

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General description

Nitroxinil is an anthelmintic agent, which is also an antiparasite. It is highly effective against Fasciola species and its mode of action involves uncoupling the oxidative phosphorylation in liver flukes and also reduces spermatogenesis in surviving flukes, resulting in fewer fertile eggs.

Application

Nitroxinil may be used as a reference standard in the determination of nitroxinil in veterinary active pharmaceutical ingredient manufacturing and bovine kidney using reversed-phase high-performance liquid chromatography (RP-HPLC) and liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD2539
BCCB1548
SZBE217XV
SZBC318XV
SZBA329XV

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W J Blanchflower et al.
The Analyst, 114(9), 1013-1015 (1989-09-01)
A method is described for the determination of nitroxynil residues in muscle, liver and kidney. The samples were extracted into diethyl ether and cleaned-up using a simple liquid-liquid extraction step. Any nitroxynil present was separated from interfering compounds by high-performance
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.
Caldow M, et al.
Journal of Chromatography A, 1216(46), 8200-8205 (2009)
C Boulard et al.
Veterinary research, 26(4), 249-255 (1995-01-01)
The responses of cattle infected with Fasciola hepatica to treatment with nitroxynil or closantel were monitored by faecal egg counts and by ELISA assay of anti-fluke antibodies. A first trial with experimentally infected heifers showed an increase in anti-fluke antibody
R Maffei Facino et al.
Arzneimittel-Forschung, 43(4), 455-460 (1993-04-01)
Liver fluke infection (Fasciola hepatica) depresses the drug-metabolizing capacity of the hepatic mixed function oxidase (MFO) and glucuronosyltransferase (GT) enzyme systems, throughout a free radicals mediated lipid peroxidation process. Glutathione (GSH, CAS 70-18-8) administered chronically (100 mg/kg i.p. once daily
M Alvinerie et al.
Journal of veterinary pharmacology and therapeutics, 14(2), 170-173 (1991-06-01)
The binding of nitroxynil to total plasma proteins of cows, sheep and rabbits was characterized using equilibrium dialysis. The data indicate clearly that nitroxynil was highly (97-98%) bound to plasma protein of each animal. This linear binding would be due
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