Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H14ClN7O |
| Molecular Weight | 319.75 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(N)=C(Cl)N=C1C(=O)NC(=N)NCC2=CC=CC=C2
InChI
InChIKey=KXDROGADUISDGY-UHFFFAOYSA-N
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)
Benzamil is a derivative of amiloride, a potassium sparing diuretic, and is an inhibitor of Na /H and Na /Ca channels. 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. Benzamil has being shown to attenuate the development of hypertension in Dahl salt-sensitive rats. Benzamil has been studied as a possible treatment for cystic fibrosis. Benzamil was suggested to be a useful sodium channel blocker for the long-term treatment of the biochemical defect in the lungs of patients with cystic fibrosis.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Epithelial ion transport of human nasal polyp and paranasal sinus mucosa. | 2007-04 |
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| Angiotensin II increases chloride absorption in the cortical collecting duct in mice through a pendrin-dependent mechanism. | 2007-03 |
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| Involvement of Na,K-pump in SEPYLRFamide-mediated reduction of cholinosensitivity in Helix neurons. | 2007-02-01 |
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| ENaC proteins contribute to VSMC migration. | 2006-12 |
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| Central receptors mediating the cardiovascular actions of melanocyte stimulating hormones. | 2006-11 |
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| The connecting tubule is the main site of the furosemide-induced urinary acidification by the vacuolar H+-ATPase. | 2006-11 |
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| Mechanism underlying flow stimulation of sodium absorption in the mammalian collecting duct. | 2006-09 |
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| Regulation of blood pressure, the epithelial sodium channel (ENaC), and other key renal sodium transporters by chronic insulin infusion in rats. | 2006-05 |
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| Intraganglionic laminar endings act as mechanoreceptors of vagal afferent nerve in guinea pig esophagus. | 2006-04-25 |
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| Heightened epithelial Na+ channel-mediated Na+ absorption in a murine polycystic kidney disease model epithelium lacking apical monocilia. | 2006-04 |
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| Calcium antagonist isradipine-induced calcium influx through nonselective cation channels in human gingival fibroblasts. | 2006-03-27 |
|
| Hyposecretion, not hyperabsorption, is the basic defect of cystic fibrosis airway glands. | 2006-03-17 |
|
| Inefficient cationic lipid-mediated siRNA and antisense oligonucleotide transfer to airway epithelial cells in vivo. | 2006-02-15 |
|
| ENaC proteins are required for NGF-induced neurite growth. | 2006-02 |
|
| Enhanced central hypertonic saline-induced activation of angiotensin II-sensitive neurons in the anterior hypothalamic area of spontaneously hypertensive and Dahl S rats. | 2006-01-30 |
|
| Potential difference measurements of ocular surface Na+ absorption analyzed using an electrokinetic model. | 2006-01 |
|
| Electrophysiological demonstration of Na+/Ca2+ exchange in bovine articular chondrocytes. | 2006 |
|
| Alpha1-adrenoceptor-mediated negative inotropic effect caused by intracellular ionic activities in guinea-pig papillary muscle. | 2005-12 |
|
| Transport of sodium and chloride across earthworm skin in vitro. | 2005-11 |
|
| Vascular ENaC proteins are required for renal myogenic constriction. | 2005-10 |
|
| Mechanisms of mechanotransduction by specialized low-threshold mechanoreceptors in the guinea pig rectum. | 2005-09 |
|
| Hemin induces active chloride secretion in Caco-2 cells. | 2005-08 |
|
| Synergic action of insulin and genistein on Na+/K+/2Cl- cotransporter in renal epithelium. | 2005-07-15 |
|
| On the interaction between amiloride and its putative alpha-subunit epithelial Na+ channel binding site. | 2005-07-15 |
|
| Central injection of hypertonic saline activates angiotensin II-sensitive neurons in the anterior hypothalamic area of rats. | 2005-06-07 |
|
| Characterization of active ion transport across primary rabbit corneal epithelial cell layers (RCrECL) cultured at an air-interface. | 2005-06 |
|
| Blockade of brain mineralocorticoid receptors or Na+ channels prevents sympathetic hyperactivity and improves cardiac function in rats post-MI. | 2005-05 |
|
| Benzamil, a blocker of epithelial Na(+) channel-induced upregulation of artery oxygen pressure level in acute lung injury rabbit ventilated with high frequency oscillation. | 2005-02-18 |
|
| Sodium and anion transport across the avian uterine (shell gland) epithelium. | 2005-02 |
|
| Evaluation of second generation amiloride analogs as therapy for cystic fibrosis lung disease. | 2004-12 |
|
| Effects of blockers of Ca2+ channels and other ion channels on in vitro excystment of Paragonimus ohirai metacercariae induced by sodium cholate. | 2004-11 |
|
| Degenerin/epithelial Na+ channel proteins: components of a vascular mechanosensor. | 2004-11 |
|
| Involvement of cytosolic Cl- in osmoregulation of alpha-ENaC gene expression. | 2004-11 |
|
| Capsazepine is a novel activator of the delta subunit of the human epithelial Na+ channel. | 2004-10-22 |
|
| Sodium-calcium exchanger contributes to membrane hyperpolarization of intact endothelial cells from rat aorta during acetylcholine stimulation. | 2004-09 |
|
| A regulated apical Na(+) conductance in dexamethasone-treated H441 airway epithelial cells. | 2004-08 |
|
| Functional expression and characterization of the human ABCG1 and ABCG4 proteins: indications for heterodimerization. | 2004-07-30 |
|
| Delayed shrinkage triggered by the Na+-K+ pump in terbutaline-stimulated rat alveolar type II cells. | 2004-07 |
|
| Glucocorticoids stimulate cation absorption by semicircular canal duct epithelium via epithelial sodium channel. | 2004-06 |
|
| Sodium transport antagonism reduces thrombotic microangiopathy in stroke-prone spontaneously hypertensive rats. | 2004-06 |
|
| Specific Na+ sensors are functionally expressed in a neuronal population of the median preoptic nucleus of the rat. | 2004-04-21 |
|
| Vasodilation of brain surface arterioles by blockade of Na-H+ antiport and its inhibition by inhibitors of KATP channel openers. | 2004-04-16 |
|
| Catecholamine clearance from alveolar spaces of rat and human lungs. | 2004-03-30 |
|
| Mechanism of apoptosis induced by diazoxide, a K+ channel opener, in HepG2 human hepatoma cells. | 2004-03 |
|
| Evidence for a protective role played by the Na+/Ca2+ exchanger in cerebral ischemia induced by middle cerebral artery occlusion in male rats. | 2004-03 |
|
| Mechanisms underlying the effects of amphetamine on particulate PKC activity. | 2004-02 |
|
| Role of sodium in intracellular calcium elevation and leukotriene B4 formation by receptor-mediated activation of human neutrophils. | 2004-01-15 |
|
| Changes in intracellular calcium concentration in response to hypertonicity in bovine articular chondrocytes. | 2004-01 |
|
| Glutamate-induced homocysteic acid release from astrocytes: possible implication in glia-neuron signaling. | 2004 |
|
| [Effect of inhibitors of sodium-calcium exchangers on acetylcholine-induced hyperpolarization of endothelial cells in rat aorta]. | 2004 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Benzamil was also used topically in humans for the treatment of the cystic fibrosis: 1.7 x 10(-3) M, or 0.9% sodium chloride) was administered topically via a nasal spray
https://www.ncbi.nlm.nih.gov/pubmed/10543294
Mice: Insulin resulted in a significant reduction in urine sodium (by approximately 80%) that was restored by intraperitoneal administration of the ENaC antagonist, benzamil (1.4 mg/kg body wt).
Route of Administration:
Intraperitoneal
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Benzamil
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DTXSID90183179
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2898-76-2
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04659UUJ94
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108107
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ACTIVE MOIETY
