9159. Terbutaline

Nomenclature

CAS number: 23031-25-6
5-[2-[(1,1-Dimethylethyl)amino]-1-hydroxyethyl]-1,3-benzenediol; α-[(tert-butylamino)methyl]-3,5-dihydroxybenzyl alcohol; 1-(3,5-dihydroxyphenyl)-2-(tert-butylamino)ethanol.
C12H19NO3; mol wt 225.28.
C 63.98%, H 8.50%, N 6.22%, O 21.31%.

Description and references

β-Adrenergic agonist. Prepn: K. Wetterlin, L. A. Svensson, BE 704932; eidem, US 3937838 (1968, 1976 both to Draco). Pharmacology: Bergman et al., Experientia 25, 899 (1969). Resolution of isomers and activity studies: K. Wetterlin, J. Med. Chem. 15, 1182 (1972). HPLC determn of enantiomers in urine: K. H. Kim et al., J. Chromatogr. B 751, 69 (2001). Clinical study in treatment of preterm labor: S. N. Caritis et al., Am. J. Obstet. Gynecol. 150, 7 (1984). Review: J. J. McPhillips in Pharmacological and Biochemical Properties of Drug Substances vol. 1, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1977) pp 311-328. Review of clinical toxicology: J. D. Truwit, Crit. Care Clin. 7, 639-657 (1991). Comprehensive description: S. Ahuja, J. Ashman, Anal. Profiles Drug Subs. 19, 601-625 (1990).

Chemical structure

Properties

Crystals from abs ether, mp 119-122°.

Derivative

Sulfate.

Nomenclature

CAS number: 23031-32-5
Brethaire (Theragenex); Brethine (Novartis); Bricanyl (AstraZeneca); Butaliret (Fatol); Monovent (AstraZeneca); Terbasmin (AstraZeneca); Terbul (AstraZeneca).
(C12H19NO3)2.H2SO4; mol wt 548.65.
C 52.54%, H 7.35%, N 5.11%, O 29.16%, S 5.84%.

Properties

mp 246-248°. uv max (0.1N HCl): 276 nm (A1%1cm 67.6). pKa1 8.8, pKa2 10.1, pKa3 11.2. Soly at 25° (mg/ml): water >20; 0.1N HCl >20; 0.1N NaOH >20; ethanol 1.2; 10% ethanol >20; methanol 2.7.

Therapeutic Category

Bronchodilator; tocolytic.

Therapeutic Category (Veterinary)

Bronchodilator.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives; Tocolytic