Oxitropium bromide
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Chemical compound
Pharmaceutical compound
| Clinical data | |
|---|---|
| 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 |
| AHFS/Drugs.com | International Drug Names |
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| Identifiers | |
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| CAS Number | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.045.543 Edit this at Wikidata |
| Chemical and physical data | |
| Formula | C19H26BrNO4 |
| Molar mass | 412.324g·mol−1 |
| 3D model (JSmol) | |
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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.[1]
It was patented in 1966 and approved for medical use in 1983.[2]
It is a thermosalient material.[3]
Synthesis
[edit ]
Two successive alkylation reactions convert a natural product, norscopolamine (1), into oxitropium bromide.[4] The first, with bromoethane, gives an N-ethyl intermediate (2), which is treated with bromomethane.[5] [6] [7]
References
[edit ]- ↑ Restrepo RD (July 2007). "Use of inhaled anticholinergic agents in obstructive airway disease". Respiratory Care. 52 (7): 833–851. PMID 17594728.
- ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 447. ISBN 9783527607495.
- ↑ Skoko Ž, Zamir S, Naumov P, Bernstein J (October 2010). "The thermosalient phenomenon. "Jumping crystals" and crystal chemistry of the anticholinergic agent oxitropium bromide". Journal of the American Chemical Society. 132 (40): 14191–14202. Bibcode:2010JAChS.13214191S. doi:10.1021/ja105508b. PMID 20860383.
- ↑ Ripperger H (June 1995). "(S)-scopolamine and (S)-norscopolamine from Atropanthe sinensis". Planta Medica. 61 (3): 292–293. Bibcode:1995PlMed..61R.292R. doi:10.1055/s-2006-958082. PMID 7617778.
- ↑ US 3472861, Banholzer R, Schulz W, Walther G, Wick H, Zeile K, "N-substitution products of norscopolamine and quaternary salts thereof", issued 14 October 1969, assigned to Boehringer Sohn Ingelheim
- ↑ US 3538102, Banholzer R, Schulz W, Zeile K, "Process for the preparation of (-)-norscopolamine", issued 3 November 1970, assigned to CH Boehringer Sohn AG and Co KG, Boehringer Ingelheim GmbH
- ↑ "Oxitropium bromide". Thieme. Archived from the original on 2024年07月04日. Retrieved 2024年07月01日.
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