Benzamil: Difference between revisions

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{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 399156235
| verifiedrevid = 413885315
| ImageFile = Benzamil.png
| ImageFile = Benzamil structure.svg
| ImageSize =
| ImageSize = 250
| IUPACName = 3,5-diamino-N-[(1E)- amino(benzylamino)methylidene]- 6-chloropyrazine-2-carboxamide
| IUPACName = 3,5-diamino-N-[(1''E'')-amino(benzylamino)methylidene]-6-chloropyrazine-2-carboxamide
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4145
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 97202
| ChemSpiderID = 97202
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C13751
| KEGG = C13751
| 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)
| 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)
| InChIKey = KXDROGADUISDGY-UHFFFAOYAA
| InChIKey = KXDROGADUISDGY-UHFFFAOYAA
| SMILES1 = Clc2nc(C(=O)NC(=N/Cc1ccccc1)/N)c(nc2N)N
| SMILES1 = Clc2nc(C(=O)NC(=N/Cc1ccccc1)/N)c(nc2N)N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 212579
| ChEMBL = 212579
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KXDROGADUISDGY-UHFFFAOYSA-N
| StdInChIKey = KXDROGADUISDGY-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 2898-76-2
| CASNo = 2898-76-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 04659UUJ94
| PubChem = 108107
| PubChem = 108107
| MeSHName=benzamil
| MeSHName=benzamil
| SMILES = Clc2nc(C(=O)\N=C(/N)NCc1ccccc1)c(N)nc2N}}
| SMILES = Clc2nc(C(=O)\N=C(/N)NCc1ccccc1)c(N)nc2N}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>13</sub>H<sub>14</sub>ClN<sub>7</sub>O
| Formula = C<sub>13</sub>H<sub>14</sub>ClN<sub>7</sub>O
| MolarMass = 319.75 g/mol
| MolarMass = 319.75 g/mol
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| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}

⚫
'''Benzamil''' or '''benzyl amiloride''' is a sodium-calcium exchange blocker.<ref>{{cite journal
'''Benzamil''' or '''benzyl amiloride''' is a potent blocker of the [[ENaC]] channel<ref>{{cite journal | last = Chalfant | first = M.L.
| quotes =
| last = Gomez-Sanchez
| year = 1995
| title = Regulation of epithelial Na+ channels from M-1 cortical collecting duct cells
⚫
| first = E. P.
| journal=American Journal of Physiology. Renal Physiology
| authorlink =
| volume=271
⚫
| coauthors = Gomez-Sanchez C. E.
| date =
| issue = 4
| pages=f861–f870
| year = 1995
| doi=10.1152/ajprenal.1996.271.4.f861| pmid = 8898016
| month = September
}}
⚫
| title = Effect of central infusion of benzamil on Dahl S rat hypertension
⚫
</ref> and also a sodium-calcium exchange blocker.<ref>{{cite journal
⚫
| last = Gomez-Sanchez | first = E. P.
⚫
|author2=Gomez-Sanchez C. E.
|date=September 1995
⚫
| title = Effect of central infusion of benzamil on Dahl S rat hypertension
| journal = Am J Physiol
| journal = Am J Physiol
| volume = 269
| volume = 269
| issue = 269(3 Pt 2)
| issue = 3, pt 2
| pages = H1044–7
| pages = H1044–7
| doi = 10.1152/ajpheart.1995.269.3.H1044
| publisher =
| location = Research Service, Harry S Truman Memorial Veterans Hospital, Columbia, Missouri, USA.
| issn =
| pmid = 7573500
| pmid = 7573500
| doi =
| bibcode =
| oclc =
| id =
| language =
| format =
| accessdate = 2008-05-01
| quote =
}}</ref><ref>
}}</ref><ref>
{{cite journal
{{cite journal
| quotes =
| last = Lee
| last = Lee
| first = Y. S.
| first = Y. S.
| authorlink =
| author2 = Sayeed, M. M.
| coauthors = Sayeed, M. M. : Wurster, R. D.
| author3 = Wurster, R. D.
| date = January 6, 1995 | title = Intracellular Ca<sup>2+</sup> mediates the cytotoxicity induced by bepridil and benzamil in human brain tumor cells.
| date = January 6, 1995
| title = Intracellular Ca<sup>2+</sup> mediates the cytotoxicity induced by bepridil and benzamil in human brain tumor cells.
| journal = : Cancer Letters
| journal = Cancer Letters
| volume = 88
| volume = 88
| issue = 1
| issue = 1
| pages = 87&ndash;91
| pages = 87&ndash;91
| publisher =
| location =
| pmid =
| doi = 10.1016/0304-3835(94)03619-T
| doi = 10.1016/0304-3835(94)03619-T
| bibcode =
| pmid = 7850778
| oclc =
| id =
| url = http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=54226
| url = http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=54226
| language =
| access-date = 2008-05-01
| format =
| url-status = dead
| archive-url = https://web.archive.org/web/20080807031224/http://grande.nal.usda.gov/ibids/index.php?mode2=detail
| accessdate = 2008-05-01
| archive-date = August 7, 2008
| laysummary =
⚫
}}</ref> It is a potent [[analog (chemistry)|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]],<ref name="pmid10543294">{{cite journal |vauthors=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 |date=September 1999 |pmid=10543294 |doi= 10.1034/j.1399-3003.1999.14c32.x|url=http://erj.ersjournals.com/cgi/pmidlookup?view=long&pmid=10543294|doi-access=free }}</ref> although with disappointing results.<ref name="pmid15273255">{{cite journal |vauthors=Hirsh AJ, Sabater JR, Zamurs A |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 |date=December 2004 |pmid=15273255 |doi=10.1124/jpet.104.071886 |s2cid=3160146 |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15273255|display-authors=etal}}</ref>
| laysource =
| laydate =
| quote =
⚫
}}</ref> It is a potent [[analog (chemistry)|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]],<ref name="pmid10543294">{{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= 10.1034/j.1399-3003.1999.14c32.x|url=http://erj.ersjournals.com/cgi/pmidlookup?view=long&pmid=10543294}}</ref> although with disappointing results.<ref name="pmid15273255">{{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}}</ref>


==Structure==
==Structure==
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==Mechanism of action==
==Mechanism of action==
[[Image:Amiloride structure.svg|thumb|150px|left|amiloride]]
[[Image:Amilorid - Amiloride.svg|thumb|200px|left|Amiloride.]]
Benzamil is closely related to [[amiloride]]. By adding the benzyl group to the nitrogen of the [[guanidine|guanidinium]] group the activity is increased several hundredfold.<ref>
Benzamil is closely related to [[amiloride]]. By adding the benzyl group to the nitrogen of the [[guanidine|guanidinium]] group the activity is increased several hundredfold.<ref>
{{cite journal
{{cite journal
| quotes =
| last = Kleyman | first = T. R.
⚫
|author2=Cragoe E. J. Jr.
| last = Kleyman
| first = T. R.
|date=October 1988
| authorlink =
⚫
| coauthors = Cragoe E. J. Jr.
| date =
| year = 1988
| month = October
| title = Amiloride and its analogs as tools in the study of ion transport
| title = Amiloride and its analogs as tools in the study of ion transport
| journal = J Membr Biol
| journal = J Membr Biol
| volume = 105
| volume = 105 | issue = 1 | pages = 1&ndash;21
| issue = 1
| pages = 1&ndash;21
| publisher =
| location =
| pmid = 2852254
| pmid = 2852254
| doi = 10.1007/BF01871102
| doi = 10.1007/BF01871102
| bibcode =
| s2cid = 21071525
| oclc =
| id =
| url =
| language =
| format =
| accessdate = 2008-05-01
| laysummary =
| laysource =
| laydate =
| quote =
}}</ref>
}}</ref>


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==References==
==References==
{{Reflist}}
{{Reflist}}

==External links==
*{{Commonscatinline}}


{{Sodium channel blockers}}
{{Sodium channel blockers}}
{{Diuretics}}
{{Diuretics}}


[[Category:Sodium-calcium exchange blockers]]
[[Category:Potassium-sparing diuretics]]
[[Category:Potassium-sparing diuretics]]
[[Category:Aminopyrazines]]
[[Category:Aminopyrazines]]
[[Category:Guanidines]]
[[Category:Acylguanidines]]




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