Benzamil

Benzamil
File:Benzamil.png
IUPAC name 3,5-diamino-N-[(1E)- amino(benzylamino)methylidene]- 6-chloropyrazine-2-carboxamide
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	2898-76-2
PubChem	108107
MeSH	benzamil
SMILES
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C13H14ClN7O
Molar mass	319.75 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Benzamil or benzyl amiloride is 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

File:Amiloride structure.svg

amiloride

Benzamil is closly related to amiloride. By adding the benzyl group to the nitrogen of the guanidinium group the activity is increased several hundred-fold.

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.