Salbutamol

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Salbutamol
200px
200px
Systematic (IUPAC) name
(RS)-4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
Clinical data
Pregnancy
category
  • AU: A
  • US: C (Risk not ruled out)
Routes of
administration		 Oral, inhalational, IV
Legal status
Legal status
Pharmacokinetic data
Metabolism Hepatic
Biological half-life 1.6 hours
Excretion Renal
Identifiers
CAS Number 18559-94-9
ATC code R03AC02 (WHO) R03CC02
PubChem CID 2083
IUPHAR/BPS 558
DrugBank APRD00553
ChemSpider 1999
Chemical data
Formula C13H21NO3
Molar mass 239.311[[Script error: No such module "String".]]
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Salbutamol (INN) or albuterol (USAN) is a short-acting β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and chronic obstructive pulmonary disease. It is marketed by GlaxoSmithKline as Ventolin, Aerolin or Ventorlin depending on the market; by Cipla as Asthalin; by Schering-Plough as Proventil and by Teva as ProAir.

Salbutamol was the first selective Β2-receptor agonist to be marketed — in 1968. It was first sold by Allen & Hanburys under the brand name Ventolin. The drug was an instant success, and has been used for the treatment of asthma ever since.[1]

Salbutamol sulfate is usually given by the inhaled route for direct effect on bronchial smooth muscle. This is usually achieved through a metered dose inhaler (MDI), nebulizer or other proprietary delivery devices (e.g. Rotahaler or Autohaler). In these forms of delivery, the maximal effect of Salbutamol can take place within five to twenty minutes of dosing, though some relief is immediately seen. Salbutamol can also be given orally as an inhalant or intravenously.

Clinical use

Salbutamol is specifically indicated in the following conditions:

As a β2-agonist, salbutamol also finds use in obstetrics. Intravenous salbutamol can be used as a tocolytic to relax the uterine smooth muscle to delay premature labour. While preferred over agents such as atosiban and ritodrine, its role has largely been replaced by the calcium-channel blocker nifedipine which is more effective, better tolerated and orally administered.[2]

In an emergency, EMS providers consider the administration of salbutamol when they see active wheezing, bronchospasm and a past diagnosis of asthma. The drug is most often administered through a nebulizer with 6-8 liters per minute of oxygen. A normal dose is 2.5 mg in 3 mL of respiratory saline.

Side effects / health consequences

The most common side effects are of fine tremor, nervousness, headache, muscle cramps, dry mouth, and palpitation.[3] Other symptoms may be tachycardia (rapid heart rate), arrhythmias, flushing, myocardial ischaemia, and disturbances of sleep and behaviour.[3] Rarely occurring, but of importance, are allergic reactions of paradoxical bronchospasm, urticaria, angioedema, hypotension, and collapse, whilst high doses may cause hypokalaemia (low potassium levels), especially in patients with renal failure and those on certain diuretics and xanthine derivaties.[3]

File:Ventolin 2mg.JPG
Ventolin 2mg tablets made by GSK (Turkey)


Diet and bodybuilding use

Salbutamol is taken by some as an alternative to clenbuterol for purposes of fat burning,[4] and/or as a performance enhancer. Abuse of the drug may be confirmed by detection of its presence in plasma or urine, typically in the 10-500 µg/L range.[5]

Doping

Clinical studies show no compelling evidence that salbutamol and other beta 2 antagonists can increase performance in healthy athletes.[6] In spite of this, salbutamol remains on WADAs prohibited list[7] and many athletes have been banned[citation needed] for use of salbutamol.

According to two small and limited studies, performed on 8 and 16 subjects respectively, salbutamol increases the performance even for a person without asthma.[8][9][10]

Detection of use

Salbutamol may be quantified in blood or plasma to confirm a diagnosis of poisoning in hospitalized patients or to aid in a medicolegal death investigation. Urinary salbutamol concentrations are frequently measured in competitive sports programs, for which a level in excess of 1000 μg/L is considered to represent abuse. The window of detection for urine testing is on the order of just 24 hours, given the relatively short elimination half-life of the drug.[11][12][13]

Ban of CFC-containing inhalers

File:Cipla inhaler.jpg
Asthalin HFA inhaler made by Cipla (India)
File:Salbutamol2.JPG
The components of a salbutamol inhaler


The U.S. Food and Drug Administration (FDA) in April 2005 mandated that all (including salbutamol) inhalers containing chlorofluorocarbons (CFCs) will be prohibited in the United States as of December 31, 2008.[14] CFC inhalers had previously been given "essential use" status, exempting it from a CFC-production ban, however in accordance with the Montreal Protocol they will be phased out; in many other countries patients have been transitioned to non-CFC based inhalers using hydrofluoroalkane (HFA) propellant. Pharmaceutical manufacturers are expected to produce adequate supplies of alternative (HFA) inhalers by 2009.[citation needed]

One drawback of this transition to HFA inhalers is that, due to patent restrictions, all HFA salbutamol inhalers are "brand-name" (ProAir, Proventil, and Ventolin). They cost approximately $20 more per inhaler than existing generic CFC salbutamol inhalers. These new formulations are patented. An industry consortium was formed to spread the costs of the FDA safety studies to get propellants such as 134a and 227 approved.[15]

Generic HFA salbutamol inhalers are not expected to reach the United States market until after 2012 due to existing patents.[16]

Salbutamol is widely used, and accounts for anywhere from 78% of all bronchodilator prescriptions in 2005 to 85% in 2008.[17] However, patients in the United States who cannot tolerate the HFA salbutamol inhalers will not have a single salbutamol alternative available to them domestically after December 31, 2008.[18] The FDA did not approve any alternatives to HFA and there are few standard inhaled lung medications in the United States that come in Dry Powder Inhaler (DPI) versions. Noticeably missing is salbutamol in DPI form in the United States, although it is available in most of the rest of the world in salbutamol DPIs.

Synthesis

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Collin, D. T.; Hartely, D.; Jack, D.; Lunts, L. H. C.; Press, J. C.; Ritchie, A. C.; Toon, P.; J. Med. Chem. 1970, 13, 674.

http://dx.doi.org/10.1021/jm00298a022

See also

References

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Additional notes

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External links

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de:Salbutamol

es:Salbutamol eu:Salbutamol fr:Salbutamol it:Salbutamolo he:סאלבוטאמול hu:Szalbutamol nl:Salbutamol ja:サルブタモール no:Salbutamol pl:Salbutamol pt:Salbutamol ru:Сальбутамол

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  1. ↑ Ventolin remains a breath of fresh air for asthma sufferers, after 40 years. The Pharmaceutical Journal Vol 279 No 7473 p404-405.
  2. ↑ Rossi S (Ed.) (2004). Australian Medicines Handbook 2004 (AMH). Adelaide: Australian Medicines Handbook. ISBN 0-9578521-4-2.
  3. ↑ 3.0 3.1 3.2 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  4. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  5. ↑ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 33-35.
  6. ↑ http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2439523/
  7. ↑ www.wada-ama.org/rtecontent/document/2009_Prohibited_List_ENG_Final_20_Sept_08.pdf
  8. ↑ http://jap.physiology.org/cgi/content/full/89/2/430#SEC2
  9. ↑ http://www.pponline.co.uk/encyc/salbutamol.html
  10. ↑ http://www.ncbi.nlm.nih.gov/pubmed/15459835
  11. ↑ Bergés R, Segura J, Ventura R, Fitch KD, Morton AR, Farré M, Mas M, de La Torre X. Discrimination of prohibited oral use of salbutamol from authorized inhaled asthma treatment. Clin. Chem. 46: 1365-1375, 2000.
  12. ↑ Schweizer C, Saugy M, Kamber M. Doping test reveals high concentrations of salbutamol in a Swiss track and field athlete. Clin. J. Sport Med. 14: 312-315, 2004.
  13. ↑ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 33-35.
  14. ↑ Emily Harrison (August 2008). "Unlikely Victims of Banning CFCs—Asthma Sufferers". Scientific American. 
  15. ↑ IPAC - International Pharmaceutical Aerosol Consortium
  16. ↑ HFA inhalers replacing generic albuterol inhalers, driving up costs (pharmacist.com)
  17. ↑ IMS Health Sales & Prescription data for all inhalers sales and prescriptions (July 2008)
  18. ↑ [www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2008/ucm116903.htm FDA Advises Patients to Switch to HFA-Propelled Albuterol Inhalers Now: CFC-propelled inhalers no longer available as of Dec. 31, 2008]
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