Levosalbutamol
4787648
215568631
2008-05-28T19:52:12Z
DOI bot
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{{drugbox |
| IUPAC_name = 2-(hydroxymethyl)-4-[(1''S'')1-hydroxy-<br>2-(tert-butylamino)ethyl]phenol
| image = Levalbuterol.svg
| image2 = Levalbuterol 3D.png
| CAS_number = 18559-94-9
| ATC_prefix = R03
| ATC_suffix = AC02
| ATC_supplemental = {{ATC|R03|CC02}}
| PubChem = 123600
| DrugBank = APRD00553
| C=13 | H=21 | N=1 | O=3
| molecular_weight = 239.311 g/mol
| bioavailability =
| protein_bound =
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 1.6 hours
| excretion = Urinary
| pregnancy_AU = A
| pregnancy_US = C
| pregnancy_category =
| smiles = CC(C)(C)NC[C@@H](C1=CC(=C(C=C1)O)CO)O
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US = Rx-only
| legal_status =
| routes_of_administration = Oral, inhalational, [[Intravenous therapy|IV]]
}}
'''Levosalbutamol''' ([[International Nonproprietary Name|INN]]) or '''levalbuterol''' ([[United States Adopted Name|USAN]]), trade name '''Xopenex''', is the ''R''-[[enantiomer]] of the short-acting [[beta2-adrenergic receptor agonist|β<sub>2</sub>-adrenergic receptor agonist]] [[Salbutamol|albuterol (salbutamol)]].
==Uses==
As a [[bronchodilator]], it is used to treat [[asthma]] and [[Chronic obstructive pulmonary disease|COPD]]. In general, levalbuterol has similar [[pharmacokinetics|pharmacokinetic]] and [[pharmacodynamics|pharmacodynamic]] properties to albuterol; however, its manufacturer, [[Sepracor]], has implied (although not directly claimed) that the presence of only the ''R''-enantiomer produces fewer side effects.
Physicians sometimes elect to use levalbuterol in patients with a history of [[supraventricular tachycardia]] or other [[arrhythmias]] because it is thought that levalbuterol may produce less direct effects on β<sub>1</sub>-adrenergic receptors in the heart.{{Fact|date=March 2007}} For similar reasons, some pediatricians also use levalbuterol for patients who experience hyperactivity or jitteriness from [[racemic]] albuterol.
==Levosalbutamol vs. albuterol ==
The use of levalbuterol over the more traditionally used racemic albuterol is controversial among health care professionals. That using levalbuterol instead of albuterol produces less direct effect on β1-adrenergic receptors and/or fewer cardiac side effects has been suggested, but not consistently demonstrated by long term, well-designed clinical trials.
There are differing opinions on whether there is sufficient therapeutic benefit to using levalbuterol that outweighs the 5-10 times higher price tag.<ref>[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16291438&query_hl=21&itool=pubmed_docsum Comparison of racemic albuterol and levalbuterol in the treatment of acute asthma in the ED.]</ref><ref>[http://www.chestjournal.org/cgi/content/full/124/3/1176 Levalbuterol is not more cost-effective than albuterol for COPD.]</ref> In general, it appears that if a clinician and patient feel that a low dose of racemic mixture is causing undesirable side effects, levalbuterol may be a viable alternative.<ref>[http://pedsinreview.aappublications.org/cgi/content/full/25/3/108 Point-Counterpoint: A Comparison of Levalbuterol and Racemic Albuterol in the Treatment of Pediatric Asthma.]</ref>
==Approval==
Levalbuterol was originally available only as a solution for [[nebulizer]] and eventually become available as a [[Chlorofluorocarbon|CFC]]-free [[metered dose inhaler]] under the trade name "Xopenex HFA (levalbuterol [[tartrate]]) Inhalation Aerosol". The [[Food and Drug Administration|FDA]] approval date was on [[March 11]], [[2005]]. [http://www.xopenex.com/aboutXopenex/inhaler/xopenex-mdi-FAQs.html (See Official FAQ)]
[[Image:XOPENEX HFA.gif|thumb|left|170px|A Xopenex HFA (levalbuterol [[tartrate]]) Inhalation Aerosol [[inhaler]]]]
== Additional studies ==
In a study conducted by Bill T. Ameredes, PhD, and colleagues from the University of Pittsburgh, that concluded that in combination corticosteroids treatments the (S)-isomer found in Albuterol had a profound nullifying effect. In the (R)- albuterol isomer it shown to enhance anti-inflammatory steroid treatment. <ref name="pmid15990776">{{cite journal |author=Ameredes BT, Calhoun WJ |title=Modulation of GM-CSF release by enantiomers of beta-agonists in human airway smooth muscle |journal=J. Allergy Clin. Immunol. |volume=116 |issue=1 |pages=65–72 |year=2005 |pmid=15990776 |doi=10.1016/j.jaci.2005.03.007}}</ref>
In other works he considers the combination (R)(S)-Albuterol a problematic drug.<ref name="pmid17060667">{{cite journal |author=Ameredes BT, Calhoun WJ |title=(R)-albuterol for asthma: pro [a.k.a. (S)-albuterol for asthma: con] |journal=Am. J. Respir. Crit. Care Med. |volume=174 |issue=9 |pages=965–9; discussion 972–4 |year=2006 |pmid=17060667 |doi=10.1164/rccm.2606001}}</ref>
==References==
{{reflist|2}}
{{Drugs for obstructive airway diseases}}
{{Phenethylamines}}
[[Category:Asthma]]
[[Category:Beta-adrenergic agonists]]
[[Category:Bronchodilators]]
[[Category:Phenethylamines]]
[[pl:Lewosalbutamol]]