amiloride   

GtoPdb Ligand ID: 2421

Synonyms: amiloride HCl | Midamor®
amiloride is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: Amiloride is a loop diuretic drug.
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2D Structure
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Physico-chemical Properties
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
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
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
ENaCαβγ Hs Channel blocker - 6.7 – 7.0 pIC50 -
pIC50 6.7 – 7.0 (IC50 2x10-7 – 1x10-7 M)
ASIC1 Hs Channel blocker - 4.6 – 5.0 pIC50 -
pIC50 5.0 (IC50 1x10-5 M) ASIC1a
pIC50 4.6 – 4.7 (IC50 2.3x10-5 – 2.1x10-5 M) ASIC1b
ASIC2 Hs Channel blocker - 4.6 pIC50 -
pIC50 4.6 (IC50 2.8x10-5 M)
ASIC3 Hs Channel blocker - 4.2 – 4.8 pIC50 -
pIC50 4.2 – 4.8 (IC50 6.3x10-5 – 1.6x10-5 M) transient component only - sustained component enhanced by 200μM amiloride at pH 4
TRPC6 Mm Channel blocker Antagonist 3.9 pIC50 - 2
pIC50 3.9 (IC50 1.29x10-4 M) [2]
Voltage: -60.0 mV
TRPP2 Hs Channel blocker - 3.8 pIC50 -
pIC50 3.8 (IC50 1.43x10-4 M)
TRPA1 Mm Channel blocker Inhibition 3.3 pIC50 - 7
pIC50 3.3 [7]
Voltage: -80.0 mV
TRPC7 Hs Channel blocker - - - -
TRPV2 Hs Channel blocker - - - -
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Sodium/hydrogen exchanger 2 Oc Inhibitor Inhibition 6.3 – 7.1 pKi - 4
pKi 6.3 – 7.1 (Ki 5x10-7 – 8x10-8 M) [4]
Sodium/hydrogen exchanger 1 Rn Inhibitor Inhibition 5.8 – 6.0 pKi - 4
pKi 5.8 – 6.0 (Ki 1.6x10-6 – 1x10-6 M) [4]
Sodium/hydrogen exchanger 5 Hs Inhibitor Inhibition 4.7 pKi - 4
pKi 4.7 (Ki 2.1x10-5 M) [4]
Sodium/hydrogen exchanger 3 Rn Inhibitor Inhibition <4.0 pKi - 4
pKi <4.0 (Ki >1x10-4 M) [4]
Ligand mentioned in the following text fields