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Details

Stereochemistry ACHIRAL
Molecular Formula C6H8ClN7O
Molecular Weight 229.627
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMILORIDE

SMILES

NC(=N)NC(=O)C1=C(N)N=C(N)C(Cl)=N1

InChI

InChIKey=XSDQTOBWRPYKKA-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Amiloride, an antikaliuretic-diuretic agent, is a pyrazine-carbonyl-guanidine that is unrelated chemically to other known antikaliuretic or diuretic agents. It is an antihypertensive, potassium-sparing diuretic that was first approved for use in 1967 and helps to treat hypertension and congestive heart failure. The drug is often used in conjunction with thiazide or loop diuretics. Due to its potassium-sparing capacities, hyperkalemia (high blood potassium levels) are occasionally observed in patients taking amiloride. Amiloride works by inhibiting sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys by binding to the amiloride-sensitive sodium channels. This promotes the loss of sodium and water from the body, but without depleting potassium. It is used for as adjunctive treatment with thiazide diuretics or other kaliuretic-diuretic agents in congestive heart failure or hypertension.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Acute effects of lithium on the renal concentrating mechanism in a primate.
1975 Mar
Response of alkalinization or acidification by phytohemagglutinin is dependent on the activity of protein kinase C in human peripheral T Cells.
2001
The myocardial Na+/H+ exchanger: a potential therapeutic target for the prevention of myocardial ischaemic and reperfusion injury and attenuation of postinfarction heart failure.
2001
Maxi K+ channels co-localised with CFTR in the apical membrane of an exocrine gland acinus: possible involvement in secretion.
2001 Apr
Regulation of Na(+) transport across leech skin by peptide hormones and neurotransmitters.
2001 Apr
Contribution of amiloride-insensitive pathways to alveolar fluid clearance in adult rats.
2001 Apr
Angiotensin II type I receptor modulates intracellular free Mg2+ in renally derived cells via Na+-dependent Ca2+-independent mechanisms.
2001 Apr 27
Beta1-adrenergic agonist is a potent stimulator of alveolar fluid clearance in hyperoxic rat lungs.
2001 Feb
Oral irritation by sodium chloride: sensitization, self-desensitization, and cross-sensitization to capsaicin.
2001 Feb
Location and function of the epithelial Na channel in the cochlea.
2001 Feb
Resorptive state and cell size influence intracellular pH regulation in rabbit osteoclasts cultured on collagen-hydroxyapatite films.
2001 Feb
Mechanisms of iron transport into rat erythroid cells.
2001 Feb
The transient receptor potential protein homologue TRP6 is the essential component of vascular alpha(1)-adrenoceptor-activated Ca(2+)-permeable cation channel.
2001 Feb 16
Na(+)-dependent fluid absorption in intact perfused rat colonic crypts.
2001 Jan
Transport of [3H]MPP+ in an immortalized rat brain microvessel endothelial cell line (RBE 4).
2001 Jan
Magnesium transport in the renal distal convoluted tubule.
2001 Jan
Functional role of sodium-calcium exchange in the regulation of renal vascular resistance.
2001 Jan
Differential transduction mechanisms underlying NaCl- and KCl-induced responses in mouse taste cells.
2001 Jan
Activation of epithelial sodium channels by prostasin in Xenopus oocytes.
2001 Jun
Epithelial Na(+) channels are regulated by flow.
2001 Jun
NaCl detection thresholds: comparison of Fischer 344 and Wistar rats.
2001 Mar
Complexities of measuring antagonist potency at P2X(7) receptor orthologs.
2001 Mar
Collecting duct is a site of sodium retention in PAN nephrosis: a rationale for amiloride therapy.
2001 Mar
The distal convoluted tubule of rabbit kidney does not express a functional sodium channel.
2001 Mar
Expression and regulation of normal and polymorphic epithelial sodium channel by human lymphocytes.
2001 Mar 16
Lung epithelial ion transport in neonatal lung disease.
2001 May
Dependence of the acid-sensitive ion channel, ASIC1a, on extracellular Ca(2+) ions.
2001 May 11
Patents

Sample Use Guides

In Vivo Use Guide
MIDAMOR (Amiloride), one 5 mg tablet daily, should be added to the usual antihypertensive or diuretic dosage of a kaliuretic diuretic. The dosage may be increased to 10 mg per day, if necessary. More than two 5 mg tablets of MIDAMOR daily usually are not needed, and there is little controlled experience with such doses. If persistent hypokalemia is documented with 10 mg, the dose can be increased to 15 mg, then 20 mg, with careful monitoring of electrolytes. If it is necessary to use MIDAMOR alone (see INDICATIONS), the starting dosage should be one 5 mg tablet daily. This dosage may be increased to 10 mg per day, if necessary. More than two 5 mg tablets usually are not needed, and there is little controlled experience with such doses. If persistent hypokalemia is documented with 10 mg, the dose can be increased to 15 mg, then 20 mg, with careful monitoring of electrolytes.
Route of Administration: Oral
In Vitro Use Guide
Amiloride (10, 30, and 100 μmol/L) concentration-dependently potentiated erlotinib-induced inhibition of cell proliferation and colony formation in the 4 human pancreatic cancer cell lines.
Name Type Language
AMILORIDE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
AMILORIDE [WHO-DD]
Common Name English
AMILORIDE [MI]
Common Name English
AMICLARAN
Brand Name English
N-AMIDINO-3,5-DIAMINO-6-CHLOROPYRAZINECARBOXAMIDE
Systematic Name English
AMILORIDE [INN]
Common Name English
AMILORIDE [VANDF]
Common Name English
PYRAZINECARBOXAMIDE, 3,5-DIAMINO-N-(AMINOIMINOMETHYL)-6-CHLORO-
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000008859
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
NCI_THESAURUS C49186
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
WHO-ATC C03DB01
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
WHO-VATC QC03DB01
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
NDF-RT N0000175418
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 16
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
LIVERTOX 38
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
NCI_THESAURUS C582
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
NDF-RT N0000175359
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
Code System Code Type Description
IUPHAR
2421
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
MESH
D000584
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
RXCUI
644
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL945
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
EPA CompTox
2609-46-3
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
ECHA (EC/EINECS)
220-024-7
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
PUBCHEM
16231
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
NCI_THESAURUS
C61633
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
EVMPD
SUB05433MIG
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
MERCK INDEX
M1671
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY Merck Index
INN
2352
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
WIKIPEDIA
Amiloride
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY
CAS
2609-46-3
Created by admin on Tue Oct 22 00:34:56 UTC 2019 , Edited by admin on Tue Oct 22 00:34:56 UTC 2019
PRIMARY