Benzamil

Benzamil
Names
	IUPAC name 3,5-diamino-N-[(1E)-amino(benzylamino)methylidene]-6-chloropyrazine-2-carboxamide
Identifiers
CAS Number	2898-76-2 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL212579 ;
ChemSpider	97202 ;
IUPHAR/BPS	4145;
KEGG	C13751 ;
MeSH	benzamil
PubChem CID	108107;
UNII	04659UUJ94 ;
	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) Key: KXDROGADUISDGY-UHFFFAOYSA-N ; 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).
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	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]

Structure

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

Mechanism of action

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

↑ 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. http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=54226. Retrieved 2008-05-01.
↑ "The effect of topical benzamil and amiloride on nasal potential difference in cystic fibrosis". Eur. Respir. J. 14 (3): 693–6. September 1999. doi:10.1034/j.1399-3003.1999.14c32.x. PMID 10543294. http://erj.ersjournals.com/cgi/pmidlookup?view=long&pmid=10543294.
↑ "Evaluation of second generation amiloride analogs as therapy for cystic fibrosis lung disease". J. Pharmacol. Exp. Ther. 311 (3): 929–38. December 2004. doi:10.1124/jpet.104.071886. PMID 15273255. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15273255.
↑ 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.

External links

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[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. http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=54226. Retrieved 2008-05-01.

[pmid10543294-4] "The effect of topical benzamil and amiloride on nasal potential difference in cystic fibrosis". Eur. Respir. J. 14 (3): 693–6. September 1999. doi:10.1034/j.1399-3003.1999.14c32.x. PMID 10543294. http://erj.ersjournals.com/cgi/pmidlookup?view=long&pmid=10543294.

[pmid15273255-5] "Evaluation of second generation amiloride analogs as therapy for cystic fibrosis lung disease". J. Pharmacol. Exp. Ther. 311 (3): 929–38. December 2004. doi:10.1124/jpet.104.071886. PMID 15273255. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15273255.

[6] 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.

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Benzamil

Topic: Chemistry

Contents

Structure

Mechanism of action

References

External links