5642. Mabuterol
Nomenclature
CAS number: 56341-08-3
4-Amino-3-chloro-α-[[(1,1-dimethylethyl)amino]methyl]-5-(trifluoromethyl)benzenemethanol; 4-amino-α-[(tert-butylamino)methyl]-3-chloro-5-(trifluoromethyl)benzyl
alcohol; 1-(4′-amino-3′-chloro-5′-trifluoromethylphenyl)-2-tert-butylaminoethanol; ambuterol. C13H18ClF3N2O; mol wt 310.74.
C 50.25%, H 5.84%, Cl 11.41%, F 18.34%, N 9.02%, O 5.15%.
Description and references
Orally active β2-adrenergic agonist related to clenbuterol, q.v. Prepn and resolution of isomers: BE 808743 (1974 to Thomae); G. Engelhardt et al., US 4119710 (1978 to Boehringer Ing.); eidem, Arzneim.-Forsch. 34, 1612 (1984). Series of articles on pharmacology, pharmacokinetics, toxicology and clinical studies: ibid. 1625-1700. Toxicity data: K. Amemiya et al., ibid. 1680. Teratological study: A. M. Hoberman et al., J. Am. Coll. Toxicol. 4, 91 (1985). Determn in human urine and plasma by enzyme immunoassay: I. Yamamoto et al., J. Immunoassay 6, 261 (1985).
Derivative
dl-Form hydrochloride.Nomenclature
CAS number: 95656-48-7
KF-868; PB-868Cl; Broncholin (Kaken). C13H18ClF3N2O.HCl; mol wt 347.20.
C 44.97%, H 5.52%, Cl 20.42%, F 16.42%, N 8.07%, O 4.61%.
Properties
Crystals from ethyl acetate + ether, mp 205-206°. Fairly sol in water. LD50 in male, female mice, male, female rats (mg/kg): 41.5, 51.1, 26.4, 28.1 i.v.; 60.3, 60.0, 76.3, 78.3 i.p.; 113.0, 125.7, 117.2, 123.1 s.c.; 220.8, 199.9, 319.3, 305.6 orally (Amemiya).Derivative
d-Form hydrochloride.Nomenclature
CAS number: 95656-54-5
Properties
mp >194° (slow dec). [α]20364 +154.9° (c = 1 in methanol).Derivative
l-Form hydrochloride.Nomenclature
CAS number: 95656-55-6
Properties
mp >194° (slow dec). [α]20364 -154.8° (c = 1 in methanol).Therapeutic Category
Bronchodilator; antiasthmatic.
Keywords
β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives