7489. Pirbuterol

Nomenclature

CAS number: 38677-81-5
α6-[[(1,1-Dimethylethyl)amino]methyl]-3-hydroxy-2,6-pyridinedimethanol; 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-tert-butylaminoethyl)pyridine.
C12H20N2O3; mol wt 240.30.
C 59.98%, H 8.39%, N 11.66%, O 19.97%.

Description and references

Analog of albuterol, q.v., with β2-adrenergic stimulating activity. Prepn: W. E. Barth, DE 2204195; idem, US 3700681 (both 1972 to Pfizer). Stability study: P. C. Bansal, D. C. Monkhouse, J. Pharm. Sci. 66, 819 (1977). Biotransformation: H. M. McIlhenny, M. S. D. Ghaly, Fed. Proc. 38, 1130 (1979). Pharmacokinetics and cardiopulmonary effects in dogs: J. W. Constantine et al., J. Pharmacol. Exp. Ther. 208, 371 (1979). Comparative study in respiratory disease: A. J. Dyson, A. D. Mackay, Br. J. Dis. Chest 74, 70 (1980). Use in treatment of cardiac failure: N. A. Awan et al., Clin. Res. 28, 17A (1980); W. S. Colucci et al., N. Engl. J. Med. 305, 185 (1981); G. I. Nelson et al., Eur. Heart J. 3, 238 (1982); K. T. Weber et al., Circulation 66, 1262 (1982). Review of pharmacology and efficacy in bronchospastic disease: D. M. Richards, R. N. Brogden, Drugs 30, 6-21 (1985).

Chemical structure

Derivative

Dihydrochloride.

Nomenclature

CAS number: 38029-10-6
CP-24314-1.
C12H22Cl2N2O3; mol wt 313.22.
C 46.02%, H 7.08%, Cl 22.64%, N 8.94%, O 15.32%.

Properties

Crystals from ethanol/isopropyl ether, mp 182° (dec).

Derivative

Monoacetate.

Nomenclature

Maxair (3M Pharma); Spirolair (3M Pharma).
C14H24N2O5; mol wt 300.35.
C 55.98%, H 8.05%, N 9.33%, O 26.63%.

Properties

Freely sol in water.

Therapeutic Category

Bronchodilator.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives