amiloride   Click here for help

GtoPdb Ligand ID: 2421

Synonyms: amiloride HCl | Midamor®
Approved drug PDB Ligand
amiloride is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: Amiloride is a loop diuretic drug.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: amiloride

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 159.29
Molecular weight 229.05
XLogP -0.47
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES NC(=NC(=O)c1nc(Cl)c(nc1N)N)N
Isomeric SMILES NC(=NC(=O)c1nc(Cl)c(nc1N)N)N
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)
InChI Key XSDQTOBWRPYKKA-UHFFFAOYSA-N
References
1. Arun T, Tomassini V, Sbardella E, de Ruiter MB, Matthews L, Leite MI, Gelineau-Morel R, Cavey A, Vergo S, Craner M et al.. (2013)
Targeting ASIC1 in primary progressive multiple sclerosis: evidence of neuroprotection with amiloride.
Brain, 136 (Pt 1): 106-15. [PMID:23365093]
2. Inoue R, Okada T, Onoue H, Hara Y, Shimizu S, Naitoh S, Ito Y, Mori Y. (2001)
The transient receptor potential protein homologue TRP6 is the essential component of vascular alpha(1)-adrenoceptor-activated Ca(2+)-permeable cation channel.
Circ Res, 88 (3): 325-32. [PMID:11179201]
3. Killestein J, Kalkers NF, Polman CH. (2005)
Glutamate inhibition in MS: the neuroprotective properties of riluzole.
J Neurol Sci, 233 (1-2): 113-5. [PMID:15949499]
4. Masereel B, Pochet L, Laeckmann D. (2003)
An overview of inhibitors of Na(+)/H(+) exchanger.
Eur J Med Chem, 38 (6): 547-54. [PMID:12832126]
5. Mostert J, Heersema T, Mahajan M, Van Der Grond J, Van Buchem MA, De Keyser J. (2013)
The effect of fluoxetine on progression in progressive multiple sclerosis: a double-blind, randomized, placebo-controlled trial.
ISRN Neurol, 2013: 370943. [PMID:23984093]
6. Mostert JP, Koch MW, Heerings M, Heersema DJ, De Keyser J. (2008)
Therapeutic potential of fluoxetine in neurological disorders.
CNS Neurosci Ther, 14 (2): 153-64. [PMID:18482027]
7. Nagata K, Duggan A, Kumar G, García-Añoveros J. (2005)
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.
J Neurosci, 25 (16): 4052-61. [PMID:15843607]
8. Sieghart W, Savić MM. (2018)
International Union of Basic and Clinical Pharmacology. CVI: GABAA Receptor Subtype- and Function-selective Ligands: Key Issues in Translation to Humans.
Pharmacol Rev, 70 (4): 836-878. [PMID:30275042]
9. Waldmann R, Bassilana F, de Weille J, Champigny G, Heurteaux C, Lazdunski M. (1997)
Molecular cloning of a non-inactivating proton-gated Na+ channel specific for sensory neurons.
J Biol Chem, 272 (34): 20975-8. [PMID:9261094]
10. Waldmann R, Champigny G, Bassilana F, Heurteaux C, Lazdunski M. (1997)
A proton-gated cation channel involved in acid-sensing.
Nature, 386 (6621): 173-7. [PMID:9062189]
11. Waldmann R, Champigny G, Voilley N, Lauritzen I, Lazdunski M. (1996)
The mammalian degenerin MDEG, an amiloride-sensitive cation channel activated by mutations causing neurodegeneration in Caenorhabditis elegans.
J Biol Chem, 271 (18): 10433-6. [PMID:8631835]