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Trade names | Oxivent, Tersigan, Tersigat, Ventilat |
Other names | N-Ethylscopolammonium bromide; Ba 253; Ba 253BR-L; Ba 253Br; Hyoscine ethobromide; N-Ethylnorscopolamine methyl bromide; Scopolamine ethobromide |
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ECHA InfoCard | 100.045.543 |
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Formula | C19H26BrNO4 |
Molar mass | 412.324 g·mol |
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Oxitropium bromide (trade names Oxivent, Tersigan) is an anticholinergic used as a bronchodilator for the treatment of asthma and chronic obstructive pulmonary disease.
It was patented in 1966 and approved for medical use in 1983.
Synthesis
The natural product, norscopolamine (1), is converted by two alkylation reactions into oxitropium bromide. The first, with bromoethane, gives the N-ethyl intermediate (2), which is treated with bromomethane.
References
- Restrepo RD (July 2007). "Use of inhaled anticholinergic agents in obstructive airway disease". Respiratory Care. 52 (7): 833–51. PMID 17594728.
- Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 447. ISBN 9783527607495.
- Ripperger, H (1995). "(S)-scopolamine and (S)-norscopolamine from Atropanthe sinensis". Planta Med. 61 (3): 292–3. doi:10.1055/s-2006-958082. PMID 7617778.
- Rolf Banholzer, Werner Schulz, Gerhard Walther, Helmut Wick, Karl Zeile, U.S. patent 3,472,861 (1969 to Boehringer Sohn Ingelheim).
- Rolf Banholzer, Werner Schulz, & Karl Zeile, U.S. patent 3,538,102 (1970 to CH Boehringer Sohn AG and Co KG, Boehringer Ingelheim GmbH).
- "Oxitropium bromide". Thieme. Retrieved 2024-07-01.
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