Title: Labetalol
CAS Registry Number: 36894-69-6
CAS Name: 2-Hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]benzamide
Additional Names: 5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]salicylamide; ibidomide
Molecular Formula: C19H24N2O3
Molecular Weight: 328.41
Percent Composition: C 69.49%, H 7.37%, N 8.53%, O 14.62%
Literature References: Specific competitive antagonist at both a- and b-adrenergic receptor sites. Prepn: L. H. Lunts, D. T. Collin, DE 2032642; eidem, US 4012444 (1971, 1977 both to Allen & Hanburys). Synthesis of labetalol and enantiomers: J. E. Clifton et al., J. Med. Chem. 25, 670 (1982); and comparison of cardiovascular properties: E. H. Gold et al., ibid. 1363. Abs config of dilevalol: P. Murray-Rust et al., Acta Crystallogr. C40, 825 (1984). Adrenoceptor blocking properties: E. J. Sybertz et al., J. Pharmacol. Exp. Ther. 218, 435 (1981). HPLC determn in serum or plasma: T. F. Woodman, B. Johnson, Ther. Drug Monit. 3, 371 (1981). Metabolism in animals and man: R. Hopkins et al., Biochem. Soc. Trans. 4, 726 (1976). Toxicity: K. Shimpo et al., Hokkaido Igaku Zasshi 53, 15 (l978), C.A. 90, 66465v (1974). Review of pharmacology: R. Donnelly, G. J. A. Macphee, Clin. Pharmacokinet. 21, 95-109 (1991); of therapeutic applications in hypertension and ischemic heart disease: K. L. Goa et al., Drugs 37, 583-627 (1989).
Derivative Type: Hydrochloride
CAS Registry Number: 32780-64-6
Manufacturers' Codes: AH-5158A; Sch-15719W
Trademarks: Amipress (Dox-Al); Ipolab (Finmedical); Labelol (ELEA); Labrocol (Lagap); Normodyne (Schering); Presdate (Alfa); Pressalolo (Locatelli); Trandate (Allen & Hanburys)
Molecular Formula: C19H24N2O3.HCl
Molecular Weight: 364.87
Percent Composition: C 62.54%, H 6.91%, N 7.68%, O 13.15%, Cl 9.72%
Properties: White crystalline solid from ethanol-ethyl acetate, mp 187-189°. Sol in water, ethanol. Insol in ether, chloroform. LD50 in male, female mice, male, female rats (mg/kg): 114, 120, 113, 107 i.p.; 47, 54, 60, 53 i.v.; 1450, 1800, 4550, 4000 orally (Shimpo).
Melting point: mp 187-189°
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 114, 120, 113, 107 i.p.; 47, 54, 60, 53 i.v.; 1450, 1800, 4550, 4000 orally (Shimpo)
Derivative Type: (R,R)-Form hydrochloride
CAS Registry Number: 75659-08-4; 75659-07-3 (free base)
Additional Names: Dilevalol hydrochloride
Manufacturers' Codes: Sch-19927
Properties: Polymorphic crystals from ethanol, mp 133-134° (dec); mp 192-193.5° (dec). [a]D26 -30.6° (c = 1.0 in ethanol).
Melting point: mp 133-134° (dec); mp 192-193.5° (dec)
Optical Rotation: [a]D26 -30.6° (c = 1.0 in ethanol)
Therap-Cat: Antihypertensive.
Keywords: a-Adrenergic Blocker; ?Adrenergic Blocker; Antihypertensive; Arylethanolamine Derivatives. |