Amprolium

Amprolium
IUPAC name 5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propyl-pyrimidin-4-amine chloride
Other names 1-[(4-Amino-2-propyl-5-pyrimidinyl)methyl]-2-picolinium chloride
Identifiers
CAS number	137-88-2 N
PubChem	2178
ChemSpider	66070 Y
EC number	204-458-4
MeSH	Amprolium
ChEMBL	CHEMBL97350 Y
ATCvet code	QP51AX09
Jmol-3D images	Image 1
SMILES [Cl-].n1c(c(cnc1CCC)C[n+]2ccccc2C)N
InChI InChI=1S/C14H19N4.ClH/c1-3-6-13-16-9-12(14(15)17-13)10-18-8-5-4-7-11(18)2;/h4-5,7-9H,3,6,10H2,1-2H3,(H2,15,16,17);1H/q+1;/p-1 Y Key: LCTXBFGHZLGBNU-UHFFFAOYSA-M Y InChI=1/C14H19N4.ClH/c1-3-6-13-16-9-12(14(15)17-13)10-18-8-5-4-7-11(18)2;/h4-5,7-9H,3,6,10H2,1-2H3,(H2,15,16,17);1H/q+1;/p-1 Key: LCTXBFGHZLGBNU-REWHXWOFAP
Properties
Molecular formula	C14H19N4+ · Cl−
Molar mass	278.780 g·mol−1
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Amprolium (INN, trade names Amprovine, Amprolium, Amprol, Anticoccid) is a coccidiostat used in poultry.

Synthesis

The drug is a thiamine analogue and blocks the thiamine transporter of Eimeria 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 conjunction with sulphonamides prophylactically in chickens and cattle as a coccidiostat.

References

Sarett, Lewis H. (1960). "The hormones". Journal of Chemical Education 37 (4): 184. doi:10.1021/ed037p184.