Benzamil

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Benzamil

IUPAC name 3,5-diamino-N-[(1E)- amino(benzylamino)methylidene]- 6-chloropyrazine-2-carboxamide
Identifiers
CAS number	2898-76-2^Y
PubChem	108107
ChemSpider	97202^Y
KEGG	C13751^Y
MeSH	benzamil
ChEMBL	CHEMBL212579^Y
Jmol-3D images	Image 1 Image 2
SMILES Clc2nc(C(=O)\N=C(/N)NCc1ccccc1)c(N)nc2N Clc2nc(C(=O)NC(=N/Cc1ccccc1)/N)c(nc2N)N
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)^Y Key: KXDROGADUISDGY-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₁₃H₁₄ClN₇O
Molar mass	319.75 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

↑ 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 FLUID AND ELECTROLYTE PHYSIOLOGY volume=271 pages=f861-f870
↑ 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. PMID 7573500. Cite uses deprecated parameters (help)
↑ 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. Retrieved 2008-05-01. Cite uses deprecated parameters (help)
↑ 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.
↑ 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. Cite uses deprecated parameters (help)

v t e Channel blockers

Calcium (Ca²⁺)	Amlodipine Amrinone Anandamide Anipamil Aranidipine Azelnidipine Azimilide Barnidipine Bencyclane Benidipine Bepridil Berbamine Bevantolol Canadine Carboxyamidotriazole Caroverine Cilnidipine Cinnarizine Clentiazem Clevidipine Conotoxins Darodipine Dauricine Devapamil Diltiazem Dimeditiapramine Dotarizine Dronedarone Efonidipine Emopamil Enpiperate Eperisone Ethosuximide Falipamil Fantofarone Fasudil Felodipine Fenamic acid Fendiline Flunarizine Fostedil Gallopamil Isradipine Lacidipine Lamotrigine Lercanidipine Lidoflazine Magnesium sulfate Manidipine Manoalide Mepirodipine Mesuximide Mibefradil Monatepil Naftopidil Nicardipine Nifedipine Niguldipine Niludipin Nilvadipine Nimodipine Nisoldipine Nitrendipine Norverapamil Ochratoxin A Osthol Otilonium bromide Oxodipine Perhexiline Phensuximide Pinaverium Piperidine Pranidipine Prenylamine Risedronic acid Ryodipine Sesamodil Sodium valproate Stepholidine TROX-1 Terodiline Tetrahydropalmatine Tetrandrine Tolfenamic acid Tranilast Valnoctamide Valperinol Valproate pivoxil Valproate semisodium Valproic acid Valpromide Verapamil Ziconotide Selective VDCC ligands: 4-Methylpregabalin Atagabalin Gabapentin Gabapentin enacarbil Imagabalin PD-200,347 PD-217,014 PD-299,685 Pregabalin

Potassium (K⁺)	3,4-Diaminopyridine 4-Aminopyridine Amiodarone Bretylium Bunaftine Charybdotoxin Conotoxins Dofetilide Dronedarone E-4031 Ibutilide Linopirdine Maurotoxin Nifekalant Paxilline Sotalol Tedisamil Tetraethylammonium Vernakalant

Sodium (Na⁺)	Antiarrhythmics: Ajmaline Aprindine Disopyramide Dronedarone Encainide Flecainide Lidocaine Lorajmine Lorcainide Mexiletine Moricizine Phenytoin Pilsicainide Prajmaline Procainamide Propafenone Quinidine Sparteine Tocainide Anticonvulsants: Carbamazepine Eslicarbazepine acetate Ethotoin Fosphenytoin Licarbazepine Mephenytoin Oxcarbazepine Oxitriptyline Phenytoin Rufinamide Topiramate Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium Valproic acid Valpromide Diuretics: Amiloride Benzamil Triamterene Local anesthetics: pFBT Amylocaine Articaine Benzocaine Bupivacaine (Levobupivacaine, Ropivacaine) Butacaine Butamben Chloroprocaine Cinchocaine Cocaine Cyclomethycaine Dimethocaine Etidocaine Hexylcaine Iontocaine Lidocaine Mepivacaine Meprylcaine Metabutoxycaine Orthocaine Piperocaine Prilocaine Procaine Propoxycaine Proxymetacaine Risocaine Tetracaine Trimecaine Toxins: Conotoxins Neosaxitoxin Saxitoxin Tetrodotoxin Others: Menthol

Other	Uncategorized: Ethadione Paramethadione Phenacemide Pheneturide Trimethadione

Antihypertensives: diuretics (C03)

Sulfonamides
(and etacrynic acid)

CA inhibitors (at PT)	Acetazolamide

Loop (Na-K-Cl at AL)	Furosemide^# Bumetanide Etacrynic acid Etozoline Muzolimine Piretanide Tienilic acid Torasemide

Thiazides (Na-Cl at DCT, Calcium-sparing)	Hydrochlorothiazide^# Bendroflumethiazide Hydroflumethiazide Chlorothiazide Polythiazide Trichlormethiazide Cyclopenthiazide Methyclothiazide Cyclothiazide Mebutizide

Thiazide-likes (primarily DCT)	Quinethazone Clopamide Chlortalidone Mefruside Clofenamide Metolazone Meticrane Xipamide Indapamide Clorexolone Fenquizone

Potassium-sparing (at CD)

ESC blockers	Amiloride^# Triamterene Benzamil

Aldosterone antagonists	Spironolactone^# Eplerenone Potassium canrenoate Canrenone

Osmotic diuretics (PT, DL)

Mannitol^#
Urea

Vasopressin receptor antagonists
(DCT and CD)

tetracyclines: Demeclocycline

Other

mercurial diuretic (Mersalyl, Meralluride)
Theobromine
Cicletanine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: VAS

anat (a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot

noco/syva/cong/lyvd/tumr, sysi/epon, injr

proc, drug (C2s+n/3/4/5/7/8/9)

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