Nitroxinil

Nitroxinil is an anthelmintic, a veterinary medicine against parasitic worms in sheep and cattle.^[1] The substance is active against the liver fluke the Fasciola hepatica and to a lesser extent against thread worms in the gastrointestinal tract.^[2] 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]}

Trade namesFluconix, Dovenix, Trodax

Other namesNitroxynil

Routes of
administrationSubcutaneous in the form of an N-Ethylglucamine salt solution

ATCvet code

• QP52AG08 (WHO)

Quick facts Clinical data, Trade names ...

Nitroxinil

Structure of nitroxinil
Clinical data
Trade names	Fluconix, Dovenix, Trodax
Other names	Nitroxynil
Routes of administration	Subcutaneous in the form of an N-Ethylglucamine salt solution
ATCvet code	QP52AG08 (WHO)
Identifiers
IUPAC name 4-Hydroxy-3-iodo-5-nitrobenzonitrile
CAS Number	1689-89-0
PubChem CID	15532
UNII	9L0EXQ7125
CompTox Dashboard (EPA)	DTXSID9075117
ECHA InfoCard	100.015.350
Chemical and physical data
Formula	C7H3IN2O3
Molar mass	290.016 g·mol−1
3D model (JSmol)	Interactive image
Melting point	136–139 °C (277–282 °F)
SMILES C1=C(C=C(C(=C1[N+](=O)[O-])O)I)C#N
InChI InChI=1S/C7H3IN2O3/c8-5-1-4(3-9)2-6(7(5)11)10(12)13/h1-2,11H

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Nitroxinil was invented by May & Baker^[3] 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.^[2] It must not be administered to animals that produce milk for human consumption.^[4]