Oxitropium bromide

Chemical compound

R03BB02 (WHO)

Identifiers

IUPAC name

(8r)-6β,7β-Epoxy-8-ethyl-3α-hydroxy-1αH,5αH-tropanium bromide (−)-tropate

CAS Number

30286-75-0

ChemSpider

16735948

UNII

SF4NW7NH7C

ChEMBL

ChEMBL1697846

CompTox Dashboard (EPA)

DTXSID0023402

ECHA InfoCard100.045.543

Chemical and physical dataFormulaC₁₉H₂₆BrNO₄Molar mass412.324 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

[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

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.^[1]

It was patented in 1966 and approved for medical use in 1983.^[2]

Synthesis

The natural product, norscopolamine (1),^[3] is converted by two alkylation reactions into oxitropium bromide. The first, with bromoethane, gives the N-ethyl intermediate (2), which is treated with bromomethane.^[4] ^[5]^[6]

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.

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol
Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast