Oxitropium bromide

Oxitropium bromide
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
ATC code	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 InfoCard	100.045.543
Chemical and physical data
Formula	C19H26BrNO4
Molar mass	412.324 g·mol−1
3D 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]

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

↑ 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 2024-07-04. Retrieved 2024-07-01.

[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.

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