4555. Guaifenesin

Nomenclature

CAS number: 93-14-1
3-(2-Methoxyphenoxy)-1,2-propanediol; glycerol mono(2-methoxyphenyl) ether; glycerol α-(2-methoxyphenyl) ether; guaiacyl glyceryl ether; glyceryl guaiacyl ether; glycerol guaiacolate; α-glyceryl guaiacol ether; o-methoxyphenyl glyceryl ether; 1,2-dihydroxy-3-(2-methoxyphenoxy)propane; guaiacol glyceryl ether; guaiphenesin; guaiacuran; MY-301; XL-90; Colrex (Solvay); Mucinex (Adams); Myoscain (Sanochemia); Relaxil G (Pannon); Resyl (Novartis); Robitussin (Wyeth).
C10H14O4; mol wt 198.22.
C 60.59%, H 7.12%, O 32.29%.

Description and references

Centrally acting muscle relaxant with expectorant properties. Prepn: Marle, J. Chem. Soc. 101, 305 (1912); Yale et al., J. Am. Chem. Soc. 72, 3710 (1950); Roviralta, Astoul, ES 212920 (1954), C.A. 49, 8332b (1955). Prepn from 2-methoxyphenol and glycidol: W. Merk et al., DE 3106995; eidem, US 4390732 (1982, 1983 to Degussa AG). GLC determn in blood: W. R. Maynard, R. B. Bruce, J. Pharm. Sci. 59, 1346 (1970). Clinical use in chronic respiratory disease: D. G. Workman et al., Curr. Ther. Res. 7, 665 (1965). Clinical efficacy as antitussive: J. J. Kuhn et al., Chest 82, 713 (1982). Pharmacokinetics and cardiopulmonary effects in horses: J. A. E. Hubbell et al., Am. J. Vet. Res. 41, 1751 (1980). Use in equine anesthesia: J. L. Grandy, W. N. McDonell, J. Am. Vet. Med. Assoc. 176, 619 (1980); G. J. Brouwer, Equine Vet. J. 17, 133 (1985).

Chemical structure

Properties

Minute rhombic prisms from ether, mp 78.5-79°. bp19 215°. Slightly bitter aromatic taste. One gram dissolves in 20 ml water at 25°. Much more sol in hot water; freely sol in ethanol; sol in chloroform, glycerol, propylene glycol, DMF; moderately sol in benzene. Practically insol in petr ether.

Therapeutic Category

Expectorant

Therapeutic Category (Veterinary)

Expectorant; muscle relaxant.

Keywords

Expectorant

Guaithylline: Bronchodilator; Xanthine Derivatives; Expectorant