AMPROLIUM ION

First approved in 1990

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H19N4
Molecular Weight	243.3275
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CCCC1=NC(N)=C(C[N+]2=C(C)C=CC=C2)C=N1

InChI

InChIKey=IPZFPROOBOUEIG-UHFFFAOYSA-N

InChI=1S/C14H19N4/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)/q+1

HIDE SMILES / InChI

Molecular Formula	C14H19N4
Molecular Weight	243.3275
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500010566.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=49295a3c-eb73-4832-a8a3-5c1967accb4d | https://www.ncbi.nlm.nih.gov/pubmed/11502555
Curator's Comment: Description was created based on several sources, including http://scienceinternational.com/fulltext/?doi=sciintl.2013.261.265 | http://www.merckvetmanual.com/poultry/coccidiosis/overview-of-coccidiosis-in-poultry

Amprolium Hydrochloride is a broad spectrum, potent coccidiostat (anti-protozoal) used for the treatment and prevention of Coccidiosis in cattle, goats, sheep, and poultry (chicken and turkey) in veterinary. Amprolium probably acts by inhibiting thiamine uptake by parasites and thus creates disorders in the metabolism of parasites.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Eimeria tenella 10 Target ID: CHEMBL612854 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4744839 \| https://www.ncbi.nlm.nih.gov/pubmed/1070675	Inhibitor 8504
thiamine uptake 4 Target ID: thiamine uptake Sources: https://www.ncbi.nlm.nih.gov/pubmed/11502555	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596
Coccidiosis 45 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=49295a3c-eb73-4832-a8a3-5c1967accb4d	Curative		Approved 8583	CORID Approved Use Unknown

C_max

Value	Dose	Analyte	Population
117.618 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, intravenous dose: 13 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.224 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, oral dose: 13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
0.049 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, oral dose: 13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
0.077 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	26 mg/kg single, oral dose: 26 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

AUC

Value	Dose	Analyte	Population
10.132 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, intravenous dose: 13 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.704 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, oral dose: 13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
0.233 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, oral dose: 13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
0.527 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	26 mg/kg single, oral dose: 26 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Analyte	Population
0.212 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, intravenous dose: 13 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, oral dose: 13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
4.416 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	13 mg/kg single, oral dose: 13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
5.33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10747238/	26 mg/kg single, oral dose: 26 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	AMPROLIUM plasma	Gallus Gallus domesticus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 OATP1B1 1079 BSEP 550

Drug as perpetrator

Target	Modality	Activity
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNzk3MzUifX0=	no [IC50 >1000 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNzk3MzUifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNzk3MzUifX0=	yes [Inhibition 10 uM]

PubMed

Title	Date	PubMed
Mechanism of thiamine uptake by human jejunal brush-border membrane vesicles.	2001-09	11502555
Studies on short-term application of drugs to Eimeria tenella in tissue culture.	1976-12	1070675
Eimeria tenella: anticoccidial drug activity in cell cultures.	1973-10	4744839
Amprolium and transport of thiamine in suspensions of intestinal cells.	1971	5575143
Effect of amprolium on Eimeria adenoeides in cell culture.	1970-04	5463052

Patents

Sample Use Guides

In Vivo Use Guide

Amprolium is a coccidiostat which is used for the treatment and prevention of coccidiosis in chickens, including laying hens, and turkeys. For treatment, it is administered in the drinking water at a concentration of 120 to 240 mg/l, or in the feed at a concentration of 125 mg/kg feed, for 5 to 7 days. For prevention of re-infection, it is administered in the drinking water at a concentration of 60 mg/l for 1 to 2 weeks.

Route of Administration: Oral

In Vitro Use Guide

Amprolium hydrochloride significantly decreased K. septempunctata spore viability at a concentration of 920 μg/mL. Amprolium exerts anticoccidial activity against Eimeria tenella at 100 μg/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:04:57 GMT 2025` Edited by `admin` on `Mon Mar 31 21:04:57 GMT 2025`
Record UNII	H2T307KMZR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMPROLIUM ION

Common Name

English

PICOLINIUM, 1-((4-AMINO-2-PROPYL-5-PYRIMIDINYL)METHYL)-2-

Preferred Name

English

PYRIDINIUM, 1-((4-AMINO-2-PROPYL-5-PYRIMIDINYL)METHYL)-2-METHYL-

Systematic Name

English

Code System Code Type Description

PUBCHEM

2178