CAS No 47141-42-4 , 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,
4-dihydro-2H-naphthalen-1-one

Title: Levobunolol
CAS Registry Number: 47141-42-4
CAS Name: 5-[(2S)-3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-1(2H)-naphthalenone
Synonyms: (-)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1(2H)-naphthalenone; l-bunolol
Manufacturers' Codes: W-6421A
Molecular Formula: C17H25NO3
Molecular Weight: 291.39
Percent Composition: C 70.07%, H 8.65%, N 4.81%, O 16.47%
Literature References: Nonselective b-adrenoceptor antagonist. Prepn of racemate: C. F. Schwender et al., J. Med. Chem. 13, 684 (1970); J. Shavel, Jr., S. Farber, DE 1948144; eidem, US 3641152 (1970, 1972 both to Warner-Lambert). Resolution of enantiomers: J. Shavel, Jr., C. F. Schwender, DE 2046043; eidem, US 3649691 (1971, 1972 both to Warner-Lambert); R. D. Dennis et al., US 4463176 (1984 to Bristol Myers, Mead Johnson). Cardiovascular pharmacology, anti-arrhythmic activity of racemate and isomers: R. D. Robson, H. R. Kaplan, J. Pharmacol. Exp. Ther. 175, 157, 168 (1970). Adrenoceptor blocking activity: H. R. Kaplan et al., Eur. J. Pharmacol. 16, 237 (1971). Metabolism in humans: F. J. DiCarlo et al., Clin. Pharmacol. Ther. 22, 858 (1977); F.-J. Leinweber et al., Pharmacology 16, 70 (1978). Corneal permeability: R. D. Schoenwald, H.-S. Huang, J. Pharm. Sci. 72, 1266, 1272 (1983). HPLC determn in biological fluids: H. Hengy, E. U. Kolle, J. Chromatogr. 338, 444 (1985); D. D. S. Tang-Liu et al., J. Liq. Chromatogr. 9, 2237 (1986). Clinical evaluation in hypertension: E. Arce-Gomez et al., Curr. Ther. Res. 19, 386 (1976); comparison with timolol, q.v., in glaucoma and ocular hypertension: A. Cinotti et al., Am. J. Ophthalmol. 99, 11 (1985); D. Long et al., ibid. 18. Review: H. R. Kaplan, "Levobunolol" in Pharmacology of Antihypertensive Drugs, A. Scriabine, Ed. (Raven Press, New York, 1980) pp 317-323. Brief review of long-term treatment of glaucoma: G. D. Novack, Gen. Pharmacol. 17, 373-377 (1986).
Properties: LD50 in male, female rats, mice (mg/kg): 700, 800, 1530, 1220 orally; 25, 28, 78, 84 i.v.; LD50 in male, female hamsters, dogs (mg/kg): 435, 500, 100, 100 orally (Kaplan, 1980).
Toxicity data: LD50 in male, female rats, mice (mg/kg): 700, 800, 1530, 1220 orally; 25, 28, 78, 84 i.v.; LD50 in male, female hamsters, dogs (mg/kg): 435, 500, 100, 100 orally (Kaplan, 1980)
 
Derivative Type: Hydrochloride
CAS Registry Number: 27912-14-7
Manufacturers' Codes: W-7000A
Trademarks: Betagan (Allergan); Vistagan (Allergan)
Molecular Formula: C17H25NO3.HCl
Molecular Weight: 327.85
Percent Composition: C 62.28%, H 7.99%, N 4.27%, O 14.64%, Cl 10.81%
Properties: Crystals from methanol-ether, mp 209-211°. [a]24589 -19.6±0.7° (c = 2.90 in methanol). uv max (NaOH): 221, 253, 310 nm (e 24700, 9000, 2400).
Melting point: mp 209-211°
Optical Rotation: [a]24589 -19.6±0.7° (c = 2.90 in methanol)
Absorption maximum: uv max (NaOH): 221, 253, 310 nm (e 24700, 9000, 2400)
 
Therap-Cat: Antiglaucoma.
Keywords: ?Adrenergic Blocker; Antiglaucoma.