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Benzamil information


Benzamil
Names
IUPAC name
3,5-diamino-N-[(1E)-amino(benzylamino)methylidene]-6-chloropyrazine-2-carboxamide
Identifiers
CAS Number
  • 2898-76-2 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEMBL
  • ChEMBL212579 checkY
ChemSpider
  • 97202 checkY
IUPHAR/BPS
  • 4145
KEGG
  • C13751 checkY
MeSH benzamil
PubChem CID
  • 108107
UNII
  • 04659UUJ94 checkY
CompTox Dashboard (EPA)
  • DTXSID90183179 Edit this at Wikidata
InChI
  • 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) checkY
    Key: KXDROGADUISDGY-UHFFFAOYSA-N checkY
  • 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)
    Key: KXDROGADUISDGY-UHFFFAOYAA
SMILES
  • Clc2nc(C(=O)\N=C(/N)NCc1ccccc1)c(N)nc2N
  • Clc2nc(C(=O)NC(=N/Cc1ccccc1)/N)c(nc2N)N
Properties
Chemical formula
C13H14ClN7O
Molar mass 319.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Benzamil or benzyl amiloride is a potent blocker of the ENaC channel[1] and also a sodium-calcium exchange blocker.[2][3] 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,[4] although with disappointing results.[5]

  1. ^ Chalfant, M.L. (1995). "Regulation of epithelial Na+ channels from M-1 cortical collecting duct cells". American Journal of Physiology. Renal Physiology. 271 (4): f861–f870. doi:10.1152/ajprenal.1996.271.4.f861. PMID 8898016.
  2. ^ Gomez-Sanchez, E. P.; Gomez-Sanchez C. E. (September 1995). "Effect of central infusion of benzamil on Dahl S rat hypertension". Am J Physiol. 269 (3, pt 2): H1044–7. doi:10.1152/ajpheart.1995.269.3.H1044. PMID 7573500.
  3. ^ Lee, Y. S.; Sayeed, M. M.; Wurster, R. D. (January 6, 1995). "Intracellular Ca2+ mediates the cytotoxicity induced by bepridil and benzamil in human brain tumor cells". Cancer Letters. 88 (1): 87–91. doi:10.1016/0304-3835(94)03619-T. PMID 7850778. Archived from the original on August 7, 2008. Retrieved 2008-05-01.
  4. ^ Rodgers HC, Knox AJ (September 1999). "The effect of topical benzamil and amiloride on nasal potential difference in cystic fibrosis". Eur. Respir. J. 14 (3): 693–6. doi:10.1034/j.1399-3003.1999.14c32.x. PMID 10543294.
  5. ^ Hirsh AJ, Sabater JR, Zamurs A, et al. (December 2004). "Evaluation of second generation amiloride analogs as therapy for cystic fibrosis lung disease". J. Pharmacol. Exp. Ther. 311 (3): 929–38. doi:10.1124/jpet.104.071886. PMID 15273255. S2CID 3160146.

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