CHEBI:2639 - amiloride

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ChEBI Name amiloride
ChEBI ID CHEBI:2639
Definition A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:47210
Supplier Information ChemicalBook:CB7146512, eMolecules:1934607, ZINC000004340269
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Amiloride, sold under the trade name Midamor among others, is a medication typically used with other medications to treat high blood pressure or swelling due to heart failure or cirrhosis of the liver. Amiloride is classified as a potassium-sparing diuretic. Amiloride is often used together with another diuretic, such as a thiazide or loop diuretic. It is taken by mouth. Onset of action is about two hours and it lasts for about a day. Common side effects include high blood potassium, vomiting, loss of appetite, rash, and headache. The risk of high blood potassium is greater in those with kidney problems, diabetes, and those who are older. Amiloride blocks the epithelial sodium channel (ENaC) in the late distal tubule, connecting tubule, and collecting duct of the nephron, which both reduces absorption of sodium ion from the lumen of the nephron and reduces excretion of potassium ion into the lumen. Amiloride was developed in 1967. It is on the World Health Organization's List of Essential Medicines.
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Formula C6H8ClN7O
Net Charge 0
Average Mass 229.62700
Monoisotopic Mass 229.04789
InChI InChI=1S/C6H8ClN7O/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11/h(H4,8,9,13)(H4,10,11,14,15)
InChIKey XSDQTOBWRPYKKA-UHFFFAOYSA-N
SMILES NC(=N)NC(=O)c1nc(Cl)c(N)nc1N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): sodium channel blocker
An agent that inhibits sodium influx through cell membranes.
Application(s): diuretic
An agent that promotes the excretion of urine through its effects on kidney function.
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ChEBI Ontology
Outgoing amiloride (CHEBI:2639) has role diuretic (CHEBI:35498)
amiloride (CHEBI:2639) has role sodium channel blocker (CHEBI:38633)
amiloride (CHEBI:2639) is a aromatic amine (CHEBI:33860)
amiloride (CHEBI:2639) is a guanidines (CHEBI:24436)
amiloride (CHEBI:2639) is a organochlorine compound (CHEBI:36683)
amiloride (CHEBI:2639) is a pyrazines (CHEBI:38314)
amiloride (CHEBI:2639) is conjugate base of amiloride(1+) (CHEBI:84745)
Incoming 5-(N,N-hexamethylene)amiloride (CHEBI:76400) has functional parent amiloride (CHEBI:2639)
5-(N-methyl-N-propyl)amiloride (CHEBI:138016) has functional parent amiloride (CHEBI:2639)
ethylisopropylamiloride (CHEBI:136538) has functional parent amiloride (CHEBI:2639)
amiloride(1+) (CHEBI:84745) is conjugate acid of amiloride (CHEBI:2639)
IUPAC Name
3,5-diamino-N-[amino(imino)methyl]-6-chloropyrazine-2-carboxamide
INNs Sources
amilorida ChemIDplus
amiloride WHO MedNet
amiloride ChEBI
amiloridum ChemIDplus
Synonyms Sources
3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide IUPAC
Amiloride KEGG COMPOUND
N-Amidino-3,5-diamino-6-chloropyrazinecarboxamide ChemIDplus
Manual Xrefs Databases
158 DrugCentral
Amiloride Wikipedia
AMR PDBeChem
BE639386 Patent
C06821 KEGG COMPOUND
CPD-10324 MetaCyc
D07447 KEGG DRUG
DB00594 DrugBank
HMDB0014732 HMDB
LSM-4194 LINCS
US3313813 Patent
View more database links
Registry Numbers Types Sources
2609-46-3 CAS Registry Number ChemIDplus
616612 Beilstein Registry Number Beilstein
657410 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
26 July 2017