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Oxitropium bromide

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Chemical compound

Pharmaceutical compound

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 namesOxivent,Tersigan) is ananticholinergic used as abronchodilator for the treatment ofasthma andchronic obstructive pulmonary disease.^[1]

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

It is athermosalient material.^[3]

Two successivealkylation reactions convert anatural product,norscopolamine (1), into oxitropium bromide.^[4] The first, withbromoethane, gives an N-ethyl intermediate (2), which is treated withbromomethane.^[5]^[6]^[7]

^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 fromthe original on 2024-07-04. Retrieved2024-07-01.

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
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Clorprenaline Ephedrine (+theophylline,+theophylline/phenobarbital,theophylline/hydroxyzine) Epinephrine^# Etafedrine Hexoprenaline Isoprenaline (isoproterenol) Methylephedrine Orciprenaline (metaproterenol) Racephedrine Tretoquinol

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthinePDE4 inhibitors	Ibudilast Roflumilast