:Nitroxinil

{{Short description|Chemical compound}}

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{{Infobox drug

| drug_name =

| INN =

| type =

| IUPAC_name = 4-Hydroxy-3-iodo-5-nitrobenzonitrile

| image = Nitroxinil Structure.svg

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| caption = Structure of nitroxinil

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| tradename = Fluconix, Dovenix, Trodax

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| pregnancy_category=

| routes_of_administration = Subcutaneous in the form of an N-Ethylglucamine salt solution

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| CAS_number = 1689-89-0

| class =

| ATCvet = yes

| ATC_prefix = P52

| ATC_suffix = AG08

| PubChem = 15532

| DrugBank =

| synonyms = Nitroxynil

| UNII = 9L0EXQ7125

| C=7|H=3|I=1|N=2|O=3

| SMILES = C1=C(C=C(C(=C1[N+](=O)[O-])O)I)C#N

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

| melting_point = 136-139

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Nitroxinil is an anthelmintic, a veterinary medicine against parasitic worms in sheep and cattle.{{cite book | vauthors = Eghianruwa K | chapter = Nitroxinil |title=Essential Drug Data for Rational Therapy in Veterinary Practice |date=2014 |publisher=AuthorHouse |location=UK |isbn=978-1-4918-0010-2 |pages=299–300}} The substance is active against the liver fluke the Fasciola hepatica and to a lesser extent against thread worms in the gastrointestinal tract.{{cite web|url=http://parasitipedia.net/index.php?option=com_content&view=article&id=2510&Itemid=2783|title=NITROXINIL = NITROXYNIL for veterinary use in CATTLE, SHEEP and GOATS against flukes and roundworms|access-date=4 April 2018}} 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.{{cn|date=December 2022}}

Nitroxinil was invented by May & Baker{{cite patent| inventor-last = May & Baker| inventor-first = | inventorlink =| inventor2-last =| inventor2-first =| inventorlink2 =| publication-date = 18 Dec 1964 | issue-date = 6 Mar 1968| title = Method for the Treatment of Helminth Infestations| country-code = GB | patent-number = 1104885}} 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. It must not be administered to animals that produce milk for human consumption.{{cite web|url=http://www.emea.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015185.pdf|title=Committee for Veterinary Medicinal Products, Nitroxinil, Summary Report|date=June 1998|publisher=The European Agency for the Evaluation of Medical Products|page=5|language=English|access-date=4 April 2018}}