Title: Nadolol
CAS Registry Number: 42200-33-9
CAS Name: 5-[3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-1,2,3,4-tetrahydro-2,3-naphthalenediol
Additional Names: 1-(tert-butylamino)-3-[(5,6,7,8-tetrahydro-cis-6,7-dihydroxy-1-naphthyl)oxy]-2-propanol; (2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol; 2,3-cis-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(tert-butylamino)propoxy]-2,3-naphthalenediol
Manufacturers' Codes: SQ-11725
Trademarks: Corgard (King); Solgol (BMS)
Molecular Formula: C17H27NO4
Molecular Weight: 309.40
Percent Composition: C 65.99%, H 8.80%, N 4.53%, O 20.68%
Literature References: b-Adrenergic blocker. Prepn: F. P. Hauck et al., DE 2258995; eidem, US 3935267 (1973, 1976, both to Squibb). Resolution of isomers: F. P. Hauck, J. E. Sundeen, DE 2421549 (1974 to Squibb), C.A. 82, 57481e (1975). Metabolism: J. Dreyfuss et al., J. Clin. Pharmacol. 17, 300 (1977). Toxicology: P. L. Sibley et al., Toxicol. Appl. Pharmacol. 44, 379 (1978). Review of pharmacology: R. C. Heel et al., Drugs 1, 1-23 (1980); M. J. Antonaccio, D. B. Evans, in Pharmacology of Antihypertensive Drugs, A. Scriabine, Ed. (Raven Press, New York, 1980) pp 295-301. Comprehensive description: L. Slusarek, K. Florey, Anal. Profiles Drug Subs. 9, 455-485 (1980). Book: International Experience with Nadolol, a Long-Acting b-Blocking Agent, F. Gross, Ed. (Grune & Stratton, New York, 1981) 229 pp.
Properties: Crystalline powder, mp 124-136°. uv max (methanol): 270, 278 nm (E1%1cm 37.5, 39.1). pKa 9.67. Freely sol in ethanol, propylene glycol; sol in hydrochloric acid; slightly sol in water, chloroform. Insol in acetone, benzene, ether, hexane. LD50 in mice, rats (mg/kg): 4500, 5300 orally (Antonaccio, Evans).
Melting point: mp 124-136°
pKa: pKa 9.67
Absorption maximum: uv max (methanol): 270, 278 nm (E1%1cm 37.5, 39.1)
Toxicity data: LD50 in mice, rats (mg/kg): 4500, 5300 orally (Antonaccio, Evans)
Therap-Cat: Antihypertensive, antianginal.
Keywords: ?Adrenergic Blocker; Antianginal; Antihypertensive; Aryloxypropanolamine Derivatives. |