Amprolium is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

sold as a coccidiostat used in

poultry Poultry () are domesticated birds kept by humans for the purpose of harvesting animal products such as meat, Eggs as food, eggs or feathers. The practice of animal husbandry, raising poultry is known as poultry farming. These birds are most typ ...

. It has many International Nonproprietary Names. __TOC__

Uses in coccidiosis treatment in poultry

The drug is a

thiamine Thiamine, also known as thiamin and vitamin B1, is a vitamin – an Nutrient#Micronutrients, essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosp ...

analogue and blocks the thiamine transporter of ''

Eimeria ''Eimeria'' is a genus of apicomplexan parasites that includes various species capable of causing the disease coccidiosis in animals such as cattle, poultry and smaller ruminants including sheep and goats. ''Eimeria'' species are considered to ...

'' species. By blocking thiamine uptake it prevents carbohydrate synthesis. Despite only moderate efficacy it is well favoured due to few resistance issues and is commonly used in the United States in conjunction with

sulfonamide In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the Chemical structure, structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this gro ...

s prophylactically in

chicken The chicken (''Gallus gallus domesticus'') is a domesticated subspecies of the red junglefowl (''Gallus gallus''), originally native to Southeast Asia. It was first domesticated around 8,000 years ago and is now one of the most common and w ...

s and

cattle Cattle (''Bos taurus'') are large, domesticated, bovid ungulates widely kept as livestock. They are prominent modern members of the subfamily Bovinae and the most widespread species of the genus '' Bos''. Mature female cattle are calle ...

as a coccidiostat.

Synthesis

Condensation of ethoxymethylenemalononitrile (1) with acetamidine (2) affords the substituted

pyrimidine Pyrimidine (; ) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The oth ...

(4). The reaction may well involve conjugate addition of the

amidine Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2. Examples of amidines includ ...

nitrogen to the

malononitrile Malononitrile is an organic compound nitrile with the formula . It is a colorless or white solid, although aged samples appear yellow or even brown. It is a widely used building block in organic synthesis. Preparation and reactions It can be pre ...

followed by loss of ethoxide (3); addition of the remaining

nitrogen to one of the nitriles will then lead to the

(4). Reduction of the nitrile gives the corresponding aminomethyl compound (5). Exhaustive

methylation Methylation, in the chemistry, chemical sciences, is the addition of a methyl group on a substrate (chemistry), substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replac ...

of the amine followed by displacement of the activated quaternary nitrogen by bromide ion affords the key intermediate (7). Displacement of the halogen by α-

picoline Picoline refers to any of three isomerism, isomers of methylpyridine (CH3C5H4N). They are all colorless liquids with a characteristic smell similar to that of pyridine. They are miscible with water and most organic solvents. Isomers The CAS reg ...

gives amprolium.

References

Antiprotozoal agents Pyridinium compounds Pyrimidines Chlorides {{antiinfective-drug-stub