5073. Ipratropium Bromide

Nomenclature

CAS number: 22254-24-6
(3-endo,8-syn)-3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane bromide; 3α-hydroxy-8-isopropyl-1αH,5αH-tropanium bromide (±)-tropate; 8-isopropylnoratropine methobromide; N-isopropylnoratropinium bromomethylate; Sch-1000; Atem (Chiesi); Atrovent (Boehringer, Ing.); Bitrop (Boehringer, Ing.); Itrop (Boehringer, Ing.); Narilet (Boehringer, Ing.); Respontin (GSK); Rinatec (Boehringer, Ing.).
C20H30BrNO3; mol wt 412.36.
C 58.25%, H 7.33%, Br 19.38%, N 3.40%, O 11.64%.

Description and references

Anticholinergic. Prepn: K. Zeile et al., ZA 6707766; eidem, US 3505337 (1968, 1970, both to Boehringer, Ing.); W. Schulz et al., Arzneim.-Forsch. 26, 960 (1976). Chemistry and pharmacokinetics: W. Deckers, Postgrad. Med. J. 51, Suppl. 7, 76 (1975). Pharmacology and toxicology: A. Engelhardt, H. Klupp, ibid. 82. Series of articles on pharmacology, toxicology, pharmacokinetics and clinical studies: Arzneim.-Forsch. 26, 974-985, 989-1020 (1976). Toxicity data: L. Sarafana et al., ibid. 985. Review: R. Bauer et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 489-515. Symposium on pharmacology, toxicology and clinical efficacy: Am. J. Med. 81(5A), 1-102 (1986). Review of clinical toxicology: J. D. Truwit, Crit. Care Clin. 7, 639-657 (1991).

Chemical structure

Properties

White crystals from n-propanol, mp 230-232°. Freely sol in water and lower alcohols. Insol in ether, chloroform and fluorohydrocarbons. Fairly stable in neutral and acid solns; rapidly hydrolyzed in alkaline soln. LD50 in male, female mice (mg/kg): 1001, 1083 orally; 12.29, 14.97 i.v.; 300, 340 s.c. LD50 in male, female rats (mg/kg): 1663, 1779 orally; 15.89, 15.70 i.v. (Sarafana).

Therapeutic Category

Bronchodilator; antiarrhythmic.

Keywords

Antiarrhythmic; Antimuscarinic; Bronchodilator; Quaternary Ammonium Compounds