Albuterol
Title: Albuterol
CAS Registry Number: 18559-94-9
CAS Name: a1-[[(1,1-Dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol
Additional Names: a1-[(tert-butylamino)methyl]-4-hydroxy-m-xylene-a,-diol; 2-(tert-butylamino)-1-(4-hydroxy-3-hydroxymethylphenyl)ethanol; 4-hydroxy-3-hydroxymethyl-a-[(tert-butylamino)methyl]benzyl alcohol; salbutamol
Manufacturers' Codes: AH-3365
Molecular Formula: C13H21NO3
Molecular Weight: 239.31
Percent Composition: C 65.25%, H 8.84%, N 5.85%, O 20.06%
Literature References: b-Adrenergic agonist. Prepn: L. H. C. Lunts et al., ZA 6705591; eidem, US 3644353 (1968, 1972 both to Allen & Hanburys). Synthesis and structure-activity studies: D. T. Collin et al., J. Med. Chem. 13, 674 (1970). Prepn of isomers: C. J. Hawkins, G. T. Klease, ibid. 16, 856 (1973); R. P. Bakale, Spec. Chem. 15, 249 (1995). Absolute configuration of isomers: D. Hartley, D. Middlemiss, J. Med. Chem. 14, 895 (1971). Pharmacology: R. T. Brittain et al., Nature 219, 862 (1968); V. A. Cullum et al., Br. J. Pharmacol. 35, 141 (1969). Metabolism: L. E. Martin et al., Eur. J. Pharmacol. 14, 183 (1971). Clinical comparison of levalbuterol with racemate: H. S. Nelson et al., J. Allergy Clin. Immunol. 102, 943 (1998). Comprehensive description: H. Y. Aboul-Enein et al., Anal. Profiles Drug Subs. 10, 665-689 (1981). Review of clinical experience in asthma and in preterm labor: A. H. Price, S. P. Clissold, Drugs 38, 77-122 (1989); of toxicology: S. E. Libretto, Arch. Toxicol. 68, 213-216 (1994). Review of clinical trials for add-on therapy to inhaled steroids: S. Shrewsbury et al., Br. Med. J. 320, 1368-1373 (2000).
Properties: Crystalline powder from ethanol-ethyl acetate or ethyl acetate-cyclohexane, mp 151° (Lunts); 157-158° (Collin). Sol in most organic solvents.
Melting point: mp 151° (Lunts); 157-158° (Collin)
 
Derivative Type: Sulfate
CAS Registry Number: 51022-70-9
Trademarks: Aerolin (3M Pharma); Asmaven (APS); Cobutolin (Cox); Ecovent (Ecosol); Loftan (GSK); Proventil (Schering-Plough); Salbulin (3M Pharma); Salbumol (GSK); Salbutard (Lusofarmaco); Salbuvent (Nycomed); Sultanol (GSK); Venetlin (Sankyo); Ventilastin (Viatris); Ventodisks (GSK); Ventolin (GSK); Volmax (GSK)
Molecular Formula: (C13H21NO3)2.H2SO4
Molecular Weight: 576.70
Percent Composition: C 54.15%, H 7.69%, N 4.86%, O 27.74%, S 5.56%
Properties: White crystalline powder. Sol in water; slightly sol in ethanol.
 
Derivative Type: (R)-Form
CAS Registry Number: 34391-04-3
Additional Names: Levalbuterol; levosalbutamol
 
Derivative Type: (R)-Form hydrochloride
CAS Registry Number: 50293-90-8
Trademarks: Xopenex (Sepracor)
Molecular Formula: C13H21NO3.HCl
Molecular Weight: 275.77
Percent Composition: C 56.62%, H 8.04%, N 5.08%, O 17.41%, Cl 12.86%
Properties: Crystallized as the monohydrate; changes crystalline form at 175°; dec 188-195°. [a]D20 -32.2° (c = 0.1 in water).
Optical Rotation: [a]D20 -32.2° (c = 0.1 in water)
 
Therap-Cat: Bronchodilator; tocolytic.
Keywords: ?Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives; Tocolytic.

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