Oxitropium bromide

Chemical compound From Wikipedia, the free encyclopedia

Oxitropium bromide (trade names Oxivent, Tersigan) is an anticholinergic used as a bronchodilator for the treatment of asthma and chronic obstructive pulmonary disease.[1]

Trade namesOxivent, Tersigan, Tersigat, Ventilat
Other namesN-Ethylscopolammonium bromide; Ba 253; Ba 253BR-L; Ba 253Br; Hyoscine ethobromide; N-Ethylnorscopolamine methyl bromide; Scopolamine ethobromide
ATC code
Quick facts Clinical data, Trade names ...
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 Edit this at Wikidata
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
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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

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