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

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

  1. ↑ Restrepo RD (July 2007). "Use of inhaled anticholinergic agents in obstructive airway disease". Respiratory Care. 52 (7): 833–851. PMID 17594728.
  2. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 447. ISBN 9783527607495.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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
  6. ↑ 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
  7. ↑ "Oxitropium bromide". Thieme. Archived from the original on 2024-07-04. Retrieved 2024-07-01.
allikas: https://en.wikipedia.org/wiki/Oxitropium_bromide