Title: Ipratropium Bromide
CAS Registry Number: 22254-24-6
CAS Name: (3-
endo,8-
syn)-3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane bromide
Synonyms: 3a-hydroxy-8-isopropyl-1a
H,5a
H-tropanium bromide (±)-tropate; 8-isopropylnoratropine methobromide;
N-isopropylnoratropinium bromomethylate
Manufacturers' Codes: Sch-1000
Trademarks: Atem (Chiesi); Atrovent (Boehringer, Ing.); Bitrop (Boehringer, Ing.); Itrop (Boehringer, Ing.); Narilet (Boehringer, Ing.); Respontin (GSK); Rinatec (Boehringer, Ing.)
Molecular Formula: C20H30BrNO3
Molecular Weight: 412.36
Percent Composition: C 58.25%, H 7.33%, Br 19.38%, N 3.40%, O 11.64%
Literature 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).
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).
Melting point: mp 230-232°
Toxicity data: 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)
Therap-Cat: Bronchodilator; antiarrhythmic.
Keywords: Antiarrhythmic; Antimuscarinic; Bronchodilator; Quaternary Ammonium Compounds.
