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]
Benzamil is closely related to amiloride. By adding the benzyl group to the nitrogen of the guanidinium group the activity is increased several hundredfold.[6]
^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.
^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.
^ Lee, Y. S.; Sayeed, M. M.; Wurster, R. D. (January 6, 1995). . 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.
^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.
^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.
^ Kleyman, T. R.; Cragoe E. J. Jr. (October 1988). "Amiloride and its analogs as tools in the study of ion transport". J Membr Biol. 105 (1): 1–21. doi:10.1007/BF01871102. PMID 2852254. S2CID 21071525.
benzamil, benzyl, amiloride, potent, blocker, enac, channel, also, sodium, calcium, exchange, blocker, potent, analog, amiloride, marketed, hydrochloride, salt, benzamil, hydrochloride, amiloride, benzamil, been, studied, possible, treatment, cystic, fibrosis,. 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 Benzamil Names IUPAC name 3 5 diamino N 1E amino benzylamino methylidene 6 chloropyrazine 2 carboxamide Identifiers CAS Number 2898 76 2 Y 3D model JSmol Interactive imageInteractive image ChEMBL ChEMBL212579 Y ChemSpider 97202 Y IUPHAR BPS 4145 KEGG C13751 Y MeSH benzamil PubChem CID 108107 UNII 04659UUJ94 Y CompTox Dashboard EPA DTXSID90183179 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 YKey KXDROGADUISDGY UHFFFAOYSA N YInChI 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 nc2NClc2nc 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 Y verify what is Y N Infobox references Contents 1 Structure 2 Mechanism of action 3 References 4 External linksStructure editBenzamil is a benzyl group containing analog of amiloride Like amiloride it is a guanidinium group containing pyrazine derivative Mechanism of action edit nbsp Amiloride Benzamil is closely related to amiloride By adding the benzyl group to the nitrogen of the guanidinium group the activity is increased several hundredfold 6 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 edit 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 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 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 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 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 Kleyman T R Cragoe E J Jr October 1988 Amiloride and its analogs as tools in the study of ion transport J Membr Biol 105 1 1 21 doi 10 1007 BF01871102 PMID 2852254 S2CID 21071525 External links edit nbsp Media related to Benzamil at Wikimedia Commons nbsp This drug article relating to the cardiovascular system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Benzamil amp oldid 1095792747, wikipedia, wiki, book, books, library,
