amprolium
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| Verifiedfields = changed
| verifiedrevid = 457129337
| ImageFile=Amprolium.svg
| ImageSize=
| PIN=1-[(4-Amino-2-propylpyrimidin-5-yl)methyl]-2-methylpyridin-1-ium chloride
| OtherNames=1-[(4-Amino-2-propyl-5-pyrimidinyl)methyl]-2-picolinium chloride, Amprovine, Amprolium, Amprol, Anticoccid
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 71M75T660B
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LCTXBFGHZLGBNU-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|changed|correct}}
| CASNo=121-25-5
| EINECS=204-458-4
| MeSHName=Amprolium
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 97350
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 85265
| PubChem=2178
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=66070
| SMILES=[Cl-].n1c(c(cnc1CCC)C[n+]2ccccc2C)N
| 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
| InChIKey = LCTXBFGHZLGBNU-REWHXWOFAP
}}
|Section2={{Chembox Properties
| Formula=C14H19N4+ · Cl−
| MolarMass=278.780 g·mol−1
| Appearance=
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| Section6 = {{Chembox Pharmacology
| Pharmacology_ref =
| ATCCode_prefix = P51
| ATCCode_suffix = BX02
| ATC_Supplemental = {{ATCvet|P51|BX52}}
| ATCvet = yes
| Licence_EU =
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| Legal_AU_comment =
| Legal_CA = Rx-only
| Legal_CA_comment = {{cite web | title=Health product highlights 2021: Annexes of products approved in 2021 | website=Health Canada | date=3 August 2022 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-product-highlights-2021/appendices.html | access-date=25 March 2024}}
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| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_AU_comment =
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|Section7={{Chembox Hazards
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Amprolium is the organic compound sold as a coccidiostat used in poultry. It has many International Nonproprietary Names.{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}{{clarify|date=May 2021}}
__TOC__
Uses in coccidiosis treatment in poultry
The drug is a thiamine analogue and blocks the thiamine transporter of Eimeria species. By blocking thiamine uptake it prevents carbohydrate synthesis.{{cn|date=December 2022}}
Despite only moderate efficacy it is well favoured due to few resistance issues and is commonly used in the United States in conjunction with sulfonamides prophylactically in chickens and cattle as a coccidiostat.{{cn|date=December 2022}}
Synthesis
Condensation of ethoxymethylenemalononitrile (1) with acetamidine (2) affords the substituted pyrimidine (4). The reaction may well involve conjugate addition of the amidine nitrogen to the malononitrile followed by loss of ethoxide (3); addition of the remaining amidine nitrogen to one of the nitriles will then lead to the pyrimidine (4). Reduction of the nitrile gives the corresponding aminomethyl compound (5). Exhaustive methylation 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 gives amprolium.
References
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