Sematilide
Title: Sematilide
CAS Registry Number: 101526-83-4
CAS Name: N-[2-(Diethylamino)ethyl]-4-[(methylsulfonyl)amino]benzamide
Manufacturers' Codes: CK-1752
Molecular Formula: C14H23N3O3S
Molecular Weight: 313.42
Percent Composition: C 53.65%, H 7.40%, N 13.41%, O 15.31%, S 10.23%
Literature References: Prepn: D. D. Davey et al., US 4544654 (1985 to Schering AG); W. C. Lumma, Jr. et al., J. Med. Chem. 30, 755 (1987). Pharmacology: S. S. Greenberg et al., Drug Dev. Res. 25, 283 (1992). Pharmacokinetics and HPLC determn in plasma: S. Dancik et al., J. Pharm. Sci. 80, 157 (1991). Clinical pharmacology: W. Wong et al., Am. J. Cardiol. 69, 206 (1992). Electrophysiologic profile: P. T. Sager et al., Circulation 88, 1072 (1993). Review: T. A. Argentieri, Cardiovasc. Drug Rev. 10, 182-198 (1992).
 
Derivative Type: Monohydrochloride
CAS Registry Number: 101526-62-9
Manufacturers' Codes: CK-1752A
Molecular Formula: C14H23N3O3S.HCl
Molecular Weight: 349.88
Percent Composition: C 48.06%, H 6.91%, N 12.01%, O 13.72%, S 9.16%, Cl 10.13%
Properties: Crystals from acetone/methanol. mp 141-142° (Lumma). Also reported as having two polymorphic crystalline forms, mp 137° and mp 142° (Argentieri). Apparent pKa1 7.60; pKa2 9.51. Distribution coefficient (octanol/pH 7.4 buffer): 0.104 at 10 mM. uv max (0.1N NaOH): 289 nm (e 1.91´104). uv max (0.1N HCl): 254 nm (e 1.78´104). LD50 i.p. in mice: 250-300 mg/kg (Lumma). LD50 in mice, rats, dogs (mg/kg): 96, 92, 143-175 i.v.; 1,800, 3,200, 500-1,000 orally (Argentieri).
Melting point: mp 141-142° (Lumma); mp 137° and mp 142° (Argentieri)
pKa: pKa1 7.60; pKa2 9.51
Absorption maximum: uv max (0.1N NaOH): 289 nm (e 1.91´104); uv max (0.1N HCl): 254 nm (e 1.78´104)
Toxicity data: LD50 i.p. in mice: 250-300 mg/kg (Lumma); LD50 in mice, rats, dogs (mg/kg): 96, 92, 143-175 i.v.; 1,800, 3,200, 500-1,000 orally (Argentieri)
 
Therap-Cat: Antiarrhythmic (class III).
Keywords: Antiarrhythmic.

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