Benzamil

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IUPACName = 3,5-diamino-N- [(1E)- amino(benzylamino)methylidene] - 6-chloropyrazine-2-carboxamide
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Section1 = Chembox Identifiers
CASNo =
PubChem = 108107
MeSHName=benzamil
SMILES = Clc2nc(C(=O)N=C(/N)NCc1ccccc1)c(N)nc2N
Section2 = Chembox Properties
Formula = C₁₃H₁₄ClN₇O
MolarMass = 319.75 g/mol
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Benzamil or benzyl amiloride is a sodium-calcium exchange blocker. [cite journal
quotes =
last = Gomez-Sanchez
first = E. P.
authorlink =
coauthors = Gomez-Sanchez C. E.
date =
year = 1995
month = Sep
title = Effect of central infusion of benzamil on Dahl S rat hypertension
journal = Am J Physiol
volume =
issue = 269(3 Pt 2)
pages = H1044-7
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location = Research Service, Harry S Truman Memorial Veterans Hospital, Columbia, Missouri, USA.
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pmid = 7573500
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id =
url = http://www.ncbi.nlm.nih.gov/pubmed/7573500
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accessdate = 2008-05-01
quote = ] [cite journal
quotes =
last = Lee
first = Y. S.
authorlink =
coauthors = Sayeed, M. M. : Wurster, R. D.
date = 6
year = 1995
month = Jan
title = Intracellular Ca²⁺ mediates the cytotoxicity induced by bepridil and benzamil in human brain tumor cells.
journal = : Cancer Letters
volume = 88
issue = 1
pages = 87–91
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location =
issn = 0304-3835
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url = http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=54226
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accessdate = 2008-05-01
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quote = ] 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,cite journal |author=Rodgers HC, Knox AJ |title=The effect of topical benzamil and amiloride on nasal potential difference in cystic fibrosis |journal=Eur. Respir. J. |volume=14 |issue=3 |pages=693–6 |year=1999 |month=September |pmid=10543294 |doi= |url=http://erj.ersjournals.com/cgi/pmidlookup?view=long&pmid=10543294] although with disappointing results.cite journal |author=Hirsh AJ, Sabater JR, Zamurs A, "et al" |title=Evaluation of second generation amiloride analogs as therapy for cystic fibrosis lung disease |journal=J. Pharmacol. Exp. Ther. |volume=311 |issue=3 |pages=929–38 |year=2004 |month=December |pmid=15273255 |doi=10.1124/jpet.104.071886 |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15273255]

tructure

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

Mechanism of action

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. [cite journal
quotes =
last = Kleyman
first = T. R.
authorlink =
coauthors = Cragoe E. J. Jr.
date =
year = 1988
month = Oct
title = Amiloride and its analogs as tools in the study of ion transport
journal = J Membr Biol
volume = 105
issue = 1
pages = 1–21
publisher =
location =
issn =
pmid = 2852254
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accessdate = 2008-05-01
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quote = ]

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.

References