Benzamil

Benzamil

Names
IUPAC name 3,5-diamino-N-[(1E)-amino(benzylamino)methylidene]-6-chloropyrazine-2-carboxamide
Identifiers
CAS Number	2898-76-2 Y
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL212579 Y
ChemSpider	97202 Y
IUPHAR/BPS	4145
KEGG	C13751 Y
MeSH	benzamil
PubChem	108107
InChI InChI=1S/C13H14ClN7O/c14-9-11(16)20-10(15)8(19-9)12(22)21-13(17)18-6-7-4-2-1-3-5-7/h1-5H,6H2,(H4,15,16,20)(H3,17,18,21,22) Y Key: KXDROGADUISDGY-UHFFFAOYSA-N Y InChI=1/C13H14ClN7O/c14-9-11(16)20-10(15)8(19-9)12(22)21-13(17)18-6-7-4-2-1-3-5-7/h1-5H,6H2,(H4,15,16,20)(H3,17,18,21,22) Key: KXDROGADUISDGY-UHFFFAOYAA
SMILES Clc2nc(C(=O)\N=C(/N)NCc1ccccc1)c(N)nc2N Clc2nc(C(=O)NC(=N/Cc1ccccc1)/N)c(nc2N)N
Properties
Chemical formula	C13H14ClN7O
Molar mass	319.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Benzamil or benzyl amiloride is a potent blocker of the ENaC channel and also a sodium-calcium exchange blocker. It is a potent analog of amiloride, and is marketed as the hydrochloride salt (benzamil hydrochloride). As amiloride, benzamil has been studied as a possible treatment for cystic fibrosis, although with disappointing results.

Structure

Benzamil is a benzyl group-containing analog of amiloride. Like amiloride, it is a guanidinium group-containing pyrazine derivative.

Mechanism of action

Amiloride.

Benzamil is closely related to amiloride. By adding the benzyl group to the nitrogen of the guanidinium group the activity is increased several hundredfold.

Amiloride works by directly blocking the epithelial sodium channel (ENaC) thereby inhibiting sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys (this mechanism is the same for triamterene). This promotes the loss of sodium and water from the body, but without depleting potassium.