Amprolium: Difference between revisions

Amprolium
Names
	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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:85265 ;
ChEMBL	ChEMBL97350 ;
ChemSpider	66070 ;
ECHA InfoCard	100.004.054
EC Number	204-458-4;
MeSH	Amprolium
PubChem CID	2178;
UNII	71M75T660B ;
CompTox Dashboard (EPA)	DTXSID10904505 ;
	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 Key: LCTXBFGHZLGBNU-UHFFFAOYSA-M ; 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;
	SMILES [Cl-].n1c(c(cnc1CCC)C[n+]2ccccc2C)N;
Properties
Chemical formula	C14H19N4+ · Cl−
Molar mass	278.780 g·mol−1
Pharmacology
ATCvet code	QP51AX09 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Browse history interactively

← Previous edit Next edit →

Content deleted Content added

VisualWikitext

Inline

Revision as of 00:22, 12 October 2016

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

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 sulfonamides prophylactically in chickens and cattle as a coccidiostat.

Synthesis

Coccidia are protozoans that can wreak havoc in a flock of poultry by an infection known as coccidiosis. Agents that control this disease–coccidiostats–are in view of the world's heavy dependence on poultry as a source of protein, of great economical significance.

Condensation of ethoxymethylenemalononitrile (1) with acetamidine (2) affords the substituted pyrimidine (4). The rxn 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 amin 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

^ Sarett, Lewis H. (1960). "The hormones". Journal of Chemical Education. 37 (4): 184. doi:10.1021/ed037p184.
^ Grewe, R. Z. Physiol. Chem. (1936).
^ "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-30. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)CS1 maint: archived copy as title (link)

This antiinfective drug article is a stub. You can help Wikipedia by expanding it.

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

[2] Grewe, R. Z. Physiol. Chem. (1936).

[3] "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-30. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)CS1 maint: archived copy as title (link)

[1]

[2]

[3]

@@ Line 56: / Line 56: @@
 ==Synthesis==
 [[Coccidia]] are protozoans that can wreak havoc in a flock of poultry by an infection known as [[coccidiosis]]. Agents that control this disease–[[coccidiostats]]–are in view of the world's heavy dependence on poultry as a source of protein, of great economical significance.
-[[File:Amprolium synthesis.svg|700px|center|thumb|Amprolium synthesis:<ref>{{Cite journal|doi=10.1021/ed037p184|title=The hormones|year=1960|last1=Sarett|first1=Lewis H.|journal=Journal of Chemical Education|volume=37|pages=184|issue=4}}</ref><ref>Grewe, R. Z. Physiol. Chem. (1936).</ref> Rogers, Sarett, {{US patent|3020277}} (1962 to Merck & Co.), see also {{US patent|3020200}} <ref>http://www.dissertationtopic.net/doc/1133386</ref>]]
+[[File:Amprolium synthesis.svg|700px|center|thumb|Amprolium synthesis:<ref>{{Cite journal|doi=10.1021/ed037p184|title=The hormones|year=1960|last1=Sarett|first1=Lewis H.|journal=Journal of Chemical Education|volume=37|pages=184|issue=4}}</ref><ref>Grewe, R. Z. Physiol. Chem. (1936).</ref> Rogers, Sarett, {{US patent|3020277}} (1962 to Merck & Co.), see also {{US patent|3020200}} <ref>{{cite web|url=http://www.dissertationtopic.net/doc/1133386 |title=Archived copy |accessdate=2015-03-30 |deadurl=yes |archiveurl=https://web.archive.org/web/20150402131023/http://www.dissertationtopic.net/doc/1133386 |archivedate=2015-04-02 |df= }}</ref>]]
 Condensation of [[ethoxymethylenemalononitrile]] ('''1''') with [[acetamidine]] ('''2''') affords the substituted [[pyrimidine]] ('''4'''). The rxn 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 amin followed by displacement of the activated [[Quaternary ammonium cation|quaternary nitrogen]] by [[bromide ion]] affords the key intermediate ('''7'''). Displacement of the halogen by α-[[picoline]] gives amprolium.