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Nitroxinil

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Nitroxinil
Structure of nitroxinil
Clinical data
Trade namesFluconix, Dovenix, Trodax
Other namesNitroxynil
Routes of
administration
Subcutaneous in the form of an N-Ethylglucamine salt solution
ATCvet code
Identifiers
  • 4-Hydroxy-3-iodo-5-nitrobenzonitrile
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.015.350 Edit this at Wikidata
Chemical and physical data
FormulaC7H3IN2O3
Molar mass290.016 g·mol−1
3D model (JSmol)
Melting point136–139 °C (277–282 °F)
  • C1=C(C=C(C(=C1[N+](=O)[O-])O)I)C#N
  • InChI=1S/C7H3IN2O3/c8-5-1-4(3-9)2-6(7(5)11)10(12)13/h1-2,11H

Nitroxinil is an anthelmintic, a veterinary medicine against parasitic worms in sheep and cattle. The substance is active against the liver fluke the Fasciola hepatica and to a lesser extent against thread worms in the gastrointestinal tract.[1] Brand names include Fluconix, Dovenix and Trodax. Nitroxynil is also used against strains of the red gum worm (Haemonchus contortus) that have become resistant to benzimidazoles.[citation needed]

Nitroxinil was invented by May & Baker[2] in the mid 1960s as part of a program into investigation of derivatives of p-hydroxybenzonitrile. In addition to Nitroxynil, the herbicides ioxynil (3,5-diiodo) and bromoxynil (3,5-dibromo) were also invented by the same company. Nitroxynil has a nitro group in addition to a single iodine group.

Nitroxynil is almost insoluble in water. It is usually injected subcutaneously into the animals in the form of the water-soluble ethylglucamine salt.[1] It must not be administered to animals that produce milk for human consumption.[3]

References

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  1. ^ a b "NITROXINIL = NITROXYNIL for veterinary use in CATTLE, SHEEP and GOATS against flukes and roundworms". Retrieved 4 April 2018.
  2. ^ GB 1104885, May & Baker, "Method for the Treatment of Helminth Infestations", published 18 Dec 1964, issued 6 Mar 1968 
  3. ^ "Committee for Veterinary Medicinal Products, Nitroxinil, Summary Report" (PDF). The European Agency for the Evaluation of Medical Products. June 1998. p. 5. Retrieved 4 April 2018.
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