Oxitropium bromide

Oxitropium bromide
Clinical data
Trade namesOxivent, Tersigan, Tersigat, Ventilat
Other namesN-Ethylscopolammonium bromide; Ba 253; Ba 253BR-L; Ba 253Br; Hyoscine ethobromide; N-Ethylnorscopolamine methyl bromide; Scopolamine ethobromide
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (8r)-6β,7β-Epoxy-8-ethyl-3α-hydroxy-1αH,5αH-tropanium bromide (−)-tropate
CAS Number
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.543
Chemical and physical data
FormulaC19H26BrNO4
Molar mass412.324 g·mol−1
3D model (JSmol)
  • [Br-].OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@@H]3[C@H]4O[C@H]4[C@H](C2)[N+]3(C)CC
  • InChI=1S/C19H26NO4.BrH/c1-3-20(2)15-9-13(10-16(20)18-17(15)24-18)23-19(22)14(11-21)12-7-5-4-6-8-12;/h4-8,13-18,21H,3,9-11H2,1-2H3;1H/q+1;/p-1/t13-,14-,15-,16+,17-,18+,20?;/m1./s1
  • Key:LCELQERNWLBPSY-KHSTUMNDSA-M

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

  1. ^ Restrepo RD (July 2007). "Use of inhaled anticholinergic agents in obstructive airway disease". Respiratory Care. 52 (7): 833–51. PMID 17594728.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 447. ISBN 9783527607495.
  3. ^ 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.
  4. ^ Rolf Banholzer, Werner Schulz, Gerhard Walther, Helmut Wick, Karl Zeile, U.S. patent 3,472,861 (1969 to Boehringer Sohn Ingelheim).
  5. ^ Rolf Banholzer, Werner Schulz, & Karl Zeile, U.S. patent 3,538,102 (1970 to CH Boehringer Sohn AG and Co KG, Boehringer Ingelheim GmbH).
  6. ^ "Oxitropium bromide". Thieme. Retrieved 2024-07-01.

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