Structural Formula Vector Image
Title: Timolol
CAS Registry Number: 26839-75-8
CAS Name: (2S)-1-[(1,1-Dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-2-propanol
Additional Names: S-(-)-3-(3-tert-butylamino-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazole; (-)-3-morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole
Molecular Formula: C13H24N4O3S
Molecular Weight: 316.42
Percent Composition: C 49.35%, H 7.65%, N 17.71%, O 15.17%, S 10.13%
Literature References: b-Adrenergic blocker. Prepn: B. K. Wasson, DE 1925956; idem, US 3655663 (1969, 1972 both to Frosst). Manufacturing process: L. M. Weinstock et al., DE 1925955; eidem, US 3657237 (1970, 1972 both to Frosst). Synthesis and activity data: Wasson et al., J. Med. Chem. 15, 651 (1972). Pharmacology: Franciosa et al., Clin. Pharmacol. Ther. 13, 138 (1972); Ulrych et al., ibid. 232. Review of efficacy in glaucoma: R. C. Heel et al., Drugs 17, 38-55 (1979). Clinical evaluation in hypertension: B. A. Rofman et al., Hypertension 2, 643 (1980). Multicenter study of effect in myocardial infarction: N. Engl. J. Med. 304, 801 (1981); of efficacy in limiting infarct size: M. Sederholm et al., ibid. 310, 9 (1984). Comprehensive description: D. J. Mazzo, A. E. Loper, Anal. Profiles Drug Subs. 16, 641-692 (1987).
Derivative Type: Hemihydrate
Properties: White, odorless, crystalline powder. Slightly sol in water; freely sol in ethanol.
Derivative Type: Hydrogen maleate salt
CAS Registry Number: 26921-17-5
Manufacturers' Codes: MK-950
Trademarks: Aquanil (Selena); Betim (Leo Pharm); Betimol (Santen); Blocadren (Merck & Co.); Proflax (Merck & Co.); Temserin (Merck & Co.); Tenopt (Sigma); Timacar (Merck & Co.); Timacor (Merck & Co.); Timoptic (Merck & Co.); Timoptol (Merck & Co.)
Molecular Formula: C13H24N4O3S.C4H4O4
Molecular Weight: 432.49
Percent Composition: C 47.21%, H 6.53%, N 12.95%, O 25.90%, S 7.41%
Properties: White crystals from ethanol, mp 201.5-202.5°. [a]24405 -12.0° (c = 5 in 1N HCl), [a]D25 -4.2°. uv max (0.1N HCl): 294 nm (A1%1cm 200). Sol in water, ethanol, methanol; sparingly sol in chloroform; very slightly sol in cyclohexane. Practically insol in isooctane, ether. Stable in soln up to pH 12.
Melting point: mp 201.5-202.5°
Optical Rotation: [a]24405 -12.0° (c = 5 in 1N HCl); [a]D25 -4.2°
Absorption maximum: uv max (0.1N HCl): 294 nm (A1%1cm 200)
Derivative Type: (±)-Free base
Properties: Crystalline solid from isopropyl ether, mp 71.5-72.5°.
Melting point: mp 71.5-72.5°
Therap-Cat: Antihypertensive; antiarrhythmic (class II); antianginal; antiglaucoma agent.
Keywords: ?Adrenergic Blocker; Antianginal; Antiarrhythmic; Antiglaucoma; Antihypertensive; Aryloxypropanolamine Derivatives.

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