Benzamil

{{chembox

| Watchedfields = changed

| verifiedrevid = 413885315

| ImageFile = Benzamil structure.svg

| ImageSize = 250

| IUPACName = 3,5-diamino-N-[(1E)-amino(benzylamino)methylidene]-6-chloropyrazine-2-carboxamide

| OtherNames =

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4145

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 97202

| KEGG_Ref = {{keggcite|correct|kegg}}

| 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)

| InChIKey = KXDROGADUISDGY-UHFFFAOYAA

| SMILES1 = Clc2nc(C(=O)NC(=N/Cc1ccccc1)/N)c(nc2N)N

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 212579

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KXDROGADUISDGY-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 2898-76-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 04659UUJ94

| 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

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Benzamil or benzyl amiloride is a potent blocker of the ENaC channel{{cite journal | last = Chalfant | first = M.L.

| year = 1995

| title = Regulation of epithelial Na+ channels from M-1 cortical collecting duct cells

| journal=American Journal of Physiology. Renal Physiology

| volume=271

| issue = 4

| pages=f861–f870

| doi=10.1152/ajprenal.1996.271.4.f861| pmid = 8898016

}}

and also a sodium-calcium exchange blocker.{{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

| volume = 269

| issue = 3, pt 2

| pages = H1044–7

| doi = 10.1152/ajpheart.1995.269.3.H1044

| pmid = 7573500

}}

{{cite journal

| last = Lee

| first = Y. S.

| author2 = Sayeed, M. M.

| author3 = Wurster, R. D.

| date = January 6, 1995

| 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

| doi = 10.1016/0304-3835(94)03619-T

| pmid = 7850778

| url = https://ods.od.nih.gov/Research/PubMed_Dietary_Supplement_Subset.aspx?mode2=detail&origin=ibids_references&therow=54226

| access-date = 2008-05-01

| url-status = live

| archive-url = https://web.archive.org/web/20080807031224/http://grande.nal.usda.gov/ibids/index.php?mode2=detail

| archive-date = August 7, 2008

| url-access = subscription

}} 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 |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 }} although with disappointing results.{{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|url-access=subscription }}