Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H14ClN7O.ClH |
| Molecular Weight | 356.21 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC1=NC(N)=C(Cl)N=C1C(=O)NC(=N)NCC2=CC=CC=C2
InChI
InChIKey=ZNWMRWWNJBXNKJ-UHFFFAOYSA-N
InChI=1S/C13H14ClN7O.ClH/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);1H
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 |
|---|---|---|
| [Mechanisms of action of hypersodium medium on contractile activity of isolated rat heart]. | 2001 |
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| Angiotensin II type I receptor modulates intracellular free Mg2+ in renally derived cells via Na+-dependent Ca2+-independent mechanisms. | 2001 Apr 27 |
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| The renal Na-HCO3-cotransporter expressed in Xenopus laevis oocytes: inhibition by tenidap and benzamil and effect of temperature on transport rate and stoichiometry. | 2001 Aug |
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| Differential roles of the sodium-calcium exchanger in renin secretion and renal vascular resistance. | 2001 Aug |
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| Inhibition of mechanical activation of guinea-pig airway afferent neurons by amiloride analogues. | 2001 Aug |
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| Isolated working rat heart adaptation after abrupt changes in extracellular Ca2+ concentration. | 2001 Jan |
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| cAMP-dependent fluid secretion in rat inner medullary collecting ducts. | 2001 Jun |
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| Antioxidant compounds and Ca(2+) pathway blockers differentially protect against methylmercury and mercuric chloride neurotoxicity. | 2001 Oct 1 |
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| CFTR disruption impairs cAMP-dependent Cl(-) secretion in primary cultures of mouse cortical collecting ducts. | 2001 Sep |
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| Brain amiloride-sensitive Phe-Met-Arg-Phe-NH(2)--gated Na(+) channels and Na(+)-induced sympathoexcitation and hypertension. | 2002 Feb |
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| Ionic mechanisms of regulatory volume increase (RVI) in the human hepatoma cell-line HepG2. | 2002 Mar |
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| Where have all the Na+ channels gone? In search of functional ENaC in exocrine pancreas. | 2002 Nov 13 |
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| [Regulation of posttetanic increase in choline sensitivity in Helix neurons by Na,K-pump: the role of Na/Ca-exchange and of mobilized calcium]. | 2002 Nov-Dec |
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| Brain sodium channels and central sodium-induced increases in brain ouabain-like compound and blood pressure. | 2003 Aug |
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| Constitutive NO synthase regulates the Na+/Ca2+ exchanger in human T cells: role of [Ca2+]i and tyrosine phosphorylation. | 2003 Aug 1 |
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| Brain sodium channels and ouabainlike compounds mediate central aldosterone-induced hypertension. | 2003 Dec |
|
| Involvement of Na/Ca exchange and intracellular mobilized Ca2+ in Na,K-pump-mediated control of depression of the cholinosensitivy of common snail neurons [correction of neorons] using a cellular analog of habituation. | 2003 Feb |
|
| Contribution of Na+ -Ca2+ exchanger to pinacidil-induced relaxation in the rat mesenteric artery. | 2003 Feb |
|
| Glutamate-induced homocysteic acid release from astrocytes: possible implication in glia-neuron signaling. | 2004 |
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| [Effect of inhibitors of sodium-calcium exchangers on acetylcholine-induced hyperpolarization of endothelial cells in rat aorta]. | 2004 |
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| Vasodilation of brain surface arterioles by blockade of Na-H+ antiport and its inhibition by inhibitors of KATP channel openers. | 2004 Apr 16 |
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| Glucocorticoids stimulate cation absorption by semicircular canal duct epithelium via epithelial sodium channel. | 2004 Jun |
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| Capsazepine is a novel activator of the delta subunit of the human epithelial Na+ channel. | 2004 Oct 22 |
|
| Synergic action of insulin and genistein on Na+/K+/2Cl- cotransporter in renal epithelium. | 2005 Jul 15 |
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| Characterization of active ion transport across primary rabbit corneal epithelial cell layers (RCrECL) cultured at an air-interface. | 2005 Jun |
|
| Transport of sodium and chloride across earthworm skin in vitro. | 2005 Nov |
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| Mechanisms of mechanotransduction by specialized low-threshold mechanoreceptors in the guinea pig rectum. | 2005 Sep |
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| Heightened epithelial Na+ channel-mediated Na+ absorption in a murine polycystic kidney disease model epithelium lacking apical monocilia. | 2006 Apr |
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| ENaC proteins are required for NGF-induced neurite growth. | 2006 Feb |
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| Central receptors mediating the cardiovascular actions of melanocyte stimulating hormones. | 2006 Nov |
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| The connecting tubule is the main site of the furosemide-induced urinary acidification by the vacuolar H+-ATPase. | 2006 Nov |
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| Epithelial ion transport of human nasal polyp and paranasal sinus mucosa. | 2007 Apr |
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| Involvement of Na,K-pump in SEPYLRFamide-mediated reduction of cholinosensitivity in Helix neurons. | 2007 Feb 1 |
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| Angiotensin II increases chloride absorption in the cortical collecting duct in mice through a pendrin-dependent mechanism. | 2007 Mar |
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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DTXSID601017145
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I7L324A070
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161804-20-2
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5702295
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ACTIVE MOIETY
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