1833. Carbuterol

Nomenclature

CAS number: 34866-47-2
[5-[2-[(1,1-Dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxyphenyl]urea; α-(t-butylaminomethyl)-4-hydroxy-3-ureidobenzyl alcohol.
C13H21N3O3; mol wt 267.32.
C 58.41%, H 7.92%, N 15.72%, O 17.96%.

Description and references

A β-adrenergic agonist related to isoproterenol, q.v., with selectivity for airway smooth muscle receptors. Prepn: C. Kaiser, S. T. Ross, DE 2106620; eidem, US 3763232 (1971, 1973 both to SKF); C. Kaiser et al., J. Med. Chem. 17, 49 (1974). Pharmacology, mechanism of action, toxicity study: J. R. Wardell et al., J. Pharmacol. Exp. Ther. 189, 167 (1974). Analysis in aq soln: L. J. Ravin et al., J. Pharm. Sci. 67, 1523 (1978). Clinical study: T. D. James, H. A. Lyons, J. Am. Med. Assoc. 241, 704 (1979).

Chemical structure

Properties

Crystals, mp 174-176°. LD50 in mice (mg/kg): 32.8 i.v.; 3134.6 orally; in rats: 77.2 i.v. (Wardell).

Derivative

Hydrochloride.

Nomenclature

CAS number: 34866-46-1
SKF-40383; Bronsecur (SK & F); Pirem (G"odecke).
C13H21N3O3.HCl; mol wt 303.79.
C 51.40%, H 7.30%, N 13.83%, O 15.80%, Cl 11.67%.

Properties

Crystals from ethanol/ether, mp 205-207° (dec).

Therapeutic Category

Bronchodilator.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives