7759. Procaterol
Nomenclature
CAS number: 72332-33-3
rel-8-Hydroxy-5-[(1R,2S)-1-hydroxy-2-[(1-methylethyl)amino]butyl]-2(1H)-quinolinone; (±)-erythro-8-hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]carbostyril. C16H22N2O3; mol wt 290.36.
C 66.18%, H 7.64%, N 9.65%, O 16.53%.
Description and references
Sympathomimetic amine with selective β2-adrenergic agonist activity. Prepn: K. Nakagawa et al., BE 823841; eidem, US 4026897 (1975, 1977 both to Otsuka); S. Yoshizaki et al., J. Med. Chem. 19, 1138 (1976). Prepn of optical isomers: eidem, ibid. 20, 1103 (1977). Assessment of selective action: H. Himori, N. Taira, Br. J. Pharmacol. 61, 9 (1977). Metabolism: Y. Yasuda et al., Arzneim.-Forsch. 29, 261 (1979). Pharmacokinetics: M. Ishigami et al., ibid. 266. Series of reproduction studies: Iyakuhin Kenkyu 10, 68-111 (1979), C.A. 90, 197728f-30a (1979). Antigenicity test: N. Nakagiri, S. Tei, Oyo Yakuri 17, 363 (1979), C.A. 91, 186577a (1979).
Derivative
Hydrochloride hemihydrate.Nomenclature
CAS number: 81262-93-3
OPC-2009; Lontermin (Lek); Masacin (Otsuka); Meptin (Otsuka); Onsukil (Otsuka); Procadil (Recordati); Promaxol (Otsuka); Propulm (DMS). C16H22N2O3.HCl. 1/2 H2O; mol wt 335.83.
C 57.22%, H 7.20%, N 8.34%, O 16.67%, Cl 10.56%.
Properties
Off-white crystalline powder, mp 193-197° (dec). Sol in methanol; slightly sol in ethanol. Practically insol in acetone, ether, ethyl acetate, chloroform, benzene. Colors on exposure to light. LD50 of the hydrochloride in male rats (mg/kg): 2600 orally, 80 i.v. (Nakagawa).Therapeutic Category
Bronchodilator.
Keywords
β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives