1307. Bitolterol

Nomenclature

CAS number: 30392-40-6
4-Methylbenzoic acid 4-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,2-phenylene ester; p-toluic acid 4-[2-(t-butylamino)-1-hydroxethyl]-o-phenylene ester; α-[(tert-butylamino)methyl]-3,4-dihydroxybenzyl alcohol 3,4-di-p-toluate.
C28H31NO5; mol wt 461.55.
C 72.86%, H 6.77%, N 3.03%, O 17.33%.

Description and references

β2-Adrenergic agonist; a diester of N-tert-butylnorepinephrine. Prepn: H. Minatoya et al., DE 2015573; eidem, US 4138581 (1970, 1979 both to Sterling); B. F. Tullar et al., J. Med. Chem. 19, 834 (1976). Pharmacology: H. Minatoya, J. Pharmacol. Exp. Ther. 206, 515 (1978). Metabolism and excretion: T. Aimoto et al., Xenobiotica 9, 173 (1979). Comparative clinical studies with isoproterenol, q.v., in asthma: J. L. Pinnas et al., J. Allergy Clin. Immunol. 79, 768 (1987); R. A. Nathan et al., ibid. 822. Review: S. B. Walker et al., Pharmacotherapy 5, 127-137 (1985).

Chemical structure

Derivative

Methanesulfonate.

Nomenclature

CAS number: 30392-41-7
Bitolterol mesylate; Win-32784; Biterol (Winthrop); Effectin (Winthrop); Tornalate (Sterling Winthrop).
C28H31NO5.CH3SO3H; mol wt 557.66.
C 62.46%, H 6.33%, N 2.51%, O 22.95%, S 5.75%.

Properties

White crystalline powder, mp 170-172°. Sol in DMSO.

Therapeutic Category

Bronchodilator.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives