Amiloride
Title: Amiloride
CAS Registry Number: 2609-46-3
CAS Name: 3,5-Diamino-N-(aminoiminomethyl)-6-chloropyrazinecarboxamide
Additional Names: N-amidino-3,5-diamino-6-chloropyrazinecarboxamide; N-amidino-3,5-diamino-6-chloropyrazinamide; 1-(3,5-diamino-6-chloropyrazinecarboxyl)guanidine; 1-(3,5-diamino-6-chloropyrazinoyl)guanidine; guanamprazine; amipramidin; amipramizide
Molecular Formula: C6H8ClN7O
Molecular Weight: 229.63
Percent Composition: C 31.38%, H 3.51%, Cl 15.44%, N 42.70%, O 6.97%
Literature References: Sodium channel blocker. Prepn: E. J. Cragoe, Jr., BE 639386; idem, US 3313813 (1964, 1967 both to Merck & Co.). NMR study on tautomerism and conformation: R. L. Smith et al., J. Am. Chem. Soc. 101, 191 (1979). Pharmacology: Baer et al., J. Pharmacol. Exp. Ther. 157, 472 (1967); Baba et al., Clin. Pharmacol. Ther. 9, 318 (1968); Lant et al., ibid. 10, 50 (1969). Metabolism: Weiss et al., ibid. 401. Clinical evaluation in cystic fibrosis: M. R. Knowles et al., N. Engl. J. Med. 322, 1189 (1990); in combination with uridine 5¢-triphosphate, q.v.: W. D. Bennett et al., Am. J. Respir. Crit. Care Med. 153, 1796 (1996). Reviews: H. L. Macfie et al., Drug Intell. Clin. Pharm. 15, 94-98 (1981); D. E. Hyams, Int. Congr. Symp. Ser. - R. Soc. Med. 44, 65-73 (1981). Comprehensive description of hydrochloride: D. J. Mazzo, Anal. Profiles Drug Subs. 15, 1-34 (1986). Review of mechanism of action: T. R. Kleyman, E. J. Cragoe, Jr., Semin. Nephrol. 8, 242-248 (1988).
Properties: Solid, mp 240.5-241.5°.
Melting point: mp 240.5-241.5°
 
Derivative Type: Hydrochloride dihydrate
CAS Registry Number: 17440-83-4
Manufacturers' Codes: MK-870
Trademarks: Amikal (GEA); Midamor (Merck & Co.); Modamide (Merck & Co.)
Molecular Formula: C6H8ClN7O.HCl.2H2O
Molecular Weight: 302.12
Percent Composition: C 23.85%, H 4.34%, Cl 23.47%, N 32.45%, O 15.89%
Properties: Crystalline solid, dec 285-288°. Anhydr, mp 293.5°. uv max (water): 212, 285, 362 nm (E1%1cm 642, 555, 617). pKa 8.7. Freely sol in DMSO, slightly sol in water, isopropanol, ethanol. Practically insol in acetone, chloroform, diethyl ether, ethyl acetate.
Melting point: mp 293.5°
pKa: pKa 8.7
Absorption maximum: uv max (water): 212, 285, 362 nm (E1%1cm 642, 555, 617)
 
Derivative Type: Hydrochloride dihydrate mixture with hydrochlorothiazide
Additional Names: Co-amilozide
Trademarks: Amil-Co (Baker Norton); Aquaretic (Azupharma); Ecodurex (Ecosol); Grodurex (Grossmann); Hexarese (Durascan); Moduretic (Merck & Co.); Moduretik (Merck & Co.); Normetic (Abbott); Normorix (Nycomed)
 
Therap-Cat: Diuretic.
Keywords: Diuretic.

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