Salbutamol
|
|
(S)-Salbutamol
|
| Systematic (IUPAC) name |
| (RS)-4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol |
| Clinical data |
| Licence data |
US FDA:link |
| Pregnancy cat. |
|
| Legal status |
- AU: Pharmacist Only (S3)
- CA: F (prescription)[1]
- UK: POM
- US: ℞-only
|
| Routes |
Oral, inhalational, IV |
| Pharmacokinetic data |
| Metabolism |
Hepatic |
| Half-life |
1.6 hours |
| Excretion |
Renal |
| Identifiers |
| CAS number |
18559-94-9 Y |
| ATC code |
R03AC02 R03CC02 |
| PubChem |
CID 2083 |
| IUPHAR ligand |
558 |
| DrugBank |
DB01001 |
| ChemSpider |
1999 Y |
| UNII |
QF8SVZ843E Y |
| KEGG |
D02147 Y |
| ChEBI |
CHEBI:2549 N |
| ChEMBL |
CHEMBL714 Y |
| Chemical data |
| Formula |
C13H21NO3 |
| Mol. mass |
239.311 |
SMILES
- OCc1cc(ccc1O)C(O)CNC(C)(C)C
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InChI
-
InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3 Y
Key:NDAUXUAQIAJITI-UHFFFAOYSA-N Y
|
| N (what is this?) (verify) |
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.[2] It is marketed as Ventolin among other brand names.
Salbutamol was the first selective β2-receptor agonist to be marketed in 1968. It was first sold by Allen & Hanburys (UK) under the brand name Ventolin, and has been used for the treatment of asthma ever since.[3] It was approved for use in the US by the Food and Drug Administration (FDA) in May 1982.[4]
Salbutamol sulfate is sold in the USA as Ventolin HFA,[5] ProAir HFA,[6] or Proventil HFA,[7] and is also available in extended release tablets.[8] It 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 20 minutes of dosing, though some relief is immediately seen. Mean duration of effect is roughly 2 hours.[9] It can also be given intravenously.[10]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[11] Compliance with the Montreal Protocol, which requires the banning of the use of ozone-layer depleting CFCs, has caused the cost of inhalers, however, to increase as much as ten-fold as generics were forced off the market from 2009 to 2013 by new patents obtained by pharmaceutical companies for non-CFC delivery systems.
Contents
- 1 Medical uses
- 2 Adverse effects
- 3 Chemistry
- 3.1 Structure-activity relationships
- 3.2 Synthesis
- 4 Society and culture
- 4.1 Bodybuilding
- 4.2 Doping
- 4.3 Detection of use
- 4.4 Brand names
- 5 See also
- 6 References
- 7 External links
Medical uses
Salbutamol is typically used to treat bronchospasm (due to any cause, allergen asthma or exercise-induced), as well as chronic obstructive pulmonary disease.[12] Emergency medical practice commonly treats people presenting with asthma who report taking their salbutamol inhaler as prescribed with salbutamol. In general, people tolerate large doses well.
Other uses include in cystic fibrosis, along with ipratropium bromide, acetylcysteine, and pulmozyme and subtypes of congenital myasthenic syndromes associated to mutations in Dok-7.[citation needed]
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 labor. 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.[13]
Salbutamol is used to treat acute hyperkalemia as it stimulates potassium to flow in cells thus lowering the level in the blood.[14][15]
Salbutamol has also been trialled in spinal muscular atrophy where it appears to show modest benefits. The drug is speculated to modulate the alternative splicing of the SMN2 gene, increasing the amount of the SMN protein whose deficiency is regarded as the root cause of the disease.[16][17]
Adverse effects
The most common side effects are fine tremor, anxiety, headache, muscle cramps, dry mouth, and palpitation.[18] Other symptoms may include tachycardia, arrhythmia, flushing, myocardial ischemia (rare), and disturbances of sleep and behaviour.[18] Rarely occurring, but of importance, are allergic reactions of paradoxical bronchospasm, urticaria, angioedema, hypotension, and collapse. High doses may cause hypokalaemia, which is of concern in patients with renal failure and those on certain diuretics and xanthine derivatives.[18]
Ventolin 2mg tablets made by GSK (Turkey)
Chemistry
(
R)-Salbutamol (top) and (
S)-salbutamol
Structure-activity relationships
The tertiary butyl group in salbutamol (or albuterol) makes it more selective for β₂-receptors. The drug is sold as a racemic mixture mainly because the (S)-enantiomer blocks metabolism pathways while the (R)-enantiomer shows activity.[19]
Synthesis
Salbutamol can be prepared from an acetophenone derivative which is itself derived from acetyl salicylic acid (hence the "sal" in salbutamol).[20]
Society and culture
Bodybuilding
Salbutamol has been shown to improve muscle weight in rats [21] and anecdotal reports hypothesise that it might be an alternative to clenbuterol for purposes of fat burning and muscle gain, with multiple studies supporting this claim.[22][23][24][25][26] Abuse of the drug may be confirmed by detection of its presence in plasma or urine, typically exceeding 1000 µg/L.[27]
Doping
Clinical studies show no compelling evidence that salbutamol and other β2-agonists can increase performance in healthy athletes.[28] In spite of this, salbutamol required "a declaration of Use in accordance with the International Standard for Therapeutic Use Exemptions" under the 2010 WADA prohibited list. This requirement was relaxed when the 2011 list was published to permit the use of "salbutamol (maximum 1600 micrograms over 24 hours) and salmeterol when taken by inhalation in accordance with the manufacturers’ recommended therapeutic regimen." [29][30]
According to two small and limited studies, performed on eight and 16 subjects, respectively, salbutamol increases the performance even for a person without asthma.[31][32][33]
Another study contradicts the above findings, however. The double blind, randomised test conducted on 12 non-asthmatic athletes concluded that salbutamol had a negligible effect on endurance performance. Nevertheless, the study also showed that the drug's bronchodilating effect may have improved respiratory adaptation at the beginning of exercise.[34]
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 forensic 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[27][35][36] (estimated at between 5 and 6 hours following oral administration of 4 mg[37]).
Brand names
It is marketed by GlaxoSmithKline as Ventolin, Ventoline, Ventilan, Aerolin or Ventorlin, depending on the market; by Cipla as Asthalin and Asthavent; by Schering-Plough as Proventil, by Teva as ProAir, Salamol or Airomir, by Beximco (Bangladesh) as AZMASOL by Ad-din Pharma as Ventosol and by Alphapharm as Asmol.
See also
- Epinephrine
- Beclometasone dipropionate
- Ipratropium/salbutamol
- Levosalbutamol
References
- ^ Health Canada
- ^ "Ventolin". HealthExpress. Retrieved 2013-09-18.
- ^ "Ventolin remains a breath of fresh air for asthma sufferers, after 40 years". The Pharmaceutical Journal 279 (7473): 404–405.
- ^ MedicineNet, Inc. http://www.medicinenet.com/albuterol/article.htm
- ^ http://www.ventolin.com/index.html
- ^ http://www.proairhfa.com/index.html .
- ^ http://www.proventilhfa.com/index.html .
- ^ http://www.vospireer.com/index.html .
- ^ Measured by a 15% increase from baseline in FEV1. "Albuterol Sulfate", Rx List: The Internet Drug Index, 6/12/2008, retrieved 2014-07-13
- ^ "Ventolin Solution for IV Infusion". Retrieved 2013-09-18.
- ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ "Albuterol". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
- ^ Rossi, S (2004). Australian Medicines Handbook. AMH. ISBN 0-9578521-4-2.
- ^ Mahoney, B. A.; Smith, W. A.; Lo, D.; Tsoi, K.; Tonelli, M.; Clase, C. (2005). "Emergency interventions for hyperkalaemia". In Clase, Catherine. Cochrane Database of Systematic Reviews. doi:10.1002/14651858.CD003235.pub2. edit
- ^ Ahee, P. (2000). "The management of hyperkalaemia in the emergency department". Emergency Medicine Journal 17 (3): 188–191. doi:10.1136/emj.17.3.188. edit
- ^ Van Meerbeke, J. P.; Sumner, C. J. (2011). "Progress and promise: The current status of spinal muscular atrophy therapeutics". Discovery medicine 12 (65): 291–305. PMID 22031667. edit
- ^ Lewelt, A.; Newcomb, T. M.; Swoboda, K. J. (2011). "New Therapeutic Approaches to Spinal Muscular Atrophy". Current Neurology and Neuroscience Reports 12 (1): 42–53. doi:10.1007/s11910-011-0240-9. PMC 3260050. PMID 22134788. edit
- ^ a b c "3.1.1.1 Selective beta2 agonists – side effects". British National Formulary (57 ed.). London: BMJ Publishing Group Ltd and Royal Pharmaceutical Society Publishing. March 2008. ISBN 0-85369-778-7.
- ^ Mehta, Akul. "Medicinal Chemistry of the Peripheral Nervous System – Adrenergics and Cholinergic their Biosynthesis, Metabolism and Structure Activity Relationships". Retrieved 2010-10-20.
- ^ Collin, David T.; Hartley, David.; Jack, David.; Lunts, Lawrence H. C.; Press, J. C.; Ritchie, Alexander C.; Toon, Paul. (1970). "Saligenin analogs of sympathomimetic catechol amines". Journal of Medicinal Chemistry 13 (4): 674–80. doi:10.1021/jm00298a022. PMID 5452431.
- ^ Carter WJ, Lynch ME (September 1994). "Comparison of the effects of salbutamol and clenbuterol on skeletal muscle mass and carcass composition in senescent rats". Metab. Clin. Exp. 43 (9): 1119–25. doi:10.1016/0026-0495(94)90054-X. PMID 7916118.
- ^ Caruso, JF; Signorile, JF; Perry, AC; Leblanc, B; Williams, R; Clark, M; Bamman, MM (Nov 1995). "The effects of albuterol and isokinetic exercise on the quadriceps muscle group.". Medicine and science in sports and exercise 27 (11): 1471–6. doi:10.1249/00005768-199511000-00002. PMID 8587482.
- ^ Caruso, J. (20 January 2005). "Albuterol aids resistance exercise in reducing unloading-induced ankle extensor strength losses". Journal of Applied Physiology 98 (5): 1705–1711. doi:10.1152/japplphysiol.01015.2004.
- ^ Caruso, John F.; Hamill, John L.; De Garmo, Nicole (2005). "Oral Albuterol Dosing During the Latter Stages of a Resistance Exercise Program". The Journal of Strength and Conditioning Research 19 (1): 102. doi:10.1519/R-14793.1.
- ^ Caruso, JF; Hamill, JL; Yamauchi, M; Mercado, DR; Cook, TD; Keller, CP; Montgomery, AG; Elias, J (Jun 2004). "Albuterol helps resistance exercise attenuate unloading-induced knee extensor losses.". Aviation, space, and environmental medicine 75 (6): 505–11. PMID 15198276.
- ^ Caruso, JF; Hamill, JL; De Garmo, N (Feb 2005). "Oral albuterol dosing during the latter stages of a resistance exercise program.". Journal of strength and conditioning research / National Strength & Conditioning Association 19 (1): 102–7. doi:10.1519/00124278-200502000-00018. PMID 15705021.
- ^ a b Baselt, R. (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Biomedical Publications,. pp. 33–35. ISBN 0-9626523-6-9.
- ^ Davis, E; Loiacono, R; Summers, R J (2008). "The rush to adrenaline: drugs in sport acting on the β-adrenergic system". British Journal of Pharmacology 154 (3): 584–97. doi:10.1038/bjp.2008.164. PMC 2439523. PMID 18500380.
- ^ "THE 2010 PROHIBITED LIST INTERNATIONAL STANDARD". WADA. Retrieved 2010-10-20.
- ^ "THE 2011 PROHIBITED LIST INTERNATIONAL STANDARD". WADA. Retrieved 2012-05-22.
- ^ Collomp, K; Candau, R; Lasne, F; Labsy, Z; Préfaut, C; De Ceaurriz, J (2000). "Effects of short-term oral salbutamol administration on exercise endurance and metabolism". Journal of applied physiology (Bethesda, Md. : 1985) 89 (2): 430–6. PMID 10926623.
- ^ Salbutamol: Ergogenic effects of salbutamol. Retrieved 2010-10-20.
- ^ Van Baak, MA; De Hon, OM; Hartgens, F; Kuipers, H (2004). "Inhaled salbutamol and endurance cycling performance in non-asthmatic athletes". International journal of sports medicine 25 (7): 533–8. doi:10.1055/s-2004-815716. PMID 15459835.
- ^ Goubault, C; Perault, MC; Leleu, E; Bouquet, S; Legros, P; Vandel, B; Denjean, A (2001). "Effects of inhaled salbutamol in exercising non-asthmatic athletes". Thorax 56 (9): 675–679. doi:10.1136/thorax.56.9.675. PMC 1746141. PMID 11514686.
- ^ Berges, Rosa; S; V; F; M; F; M; D (2000). "Discrimination of Prohibited Oral Use of Salbutamol from Authorized Inhaled Asthma Treatment". Clinical Chemistry 46 (9): 1365–75. PMID 10973867.
- ^ Schweizer, C; Saugy, M; Kamber, M (2004). "Doping test reveals high concentrations of salbutamol in a Swiss track and field athlete". Clin. J. Sport Med. 14 (5): 312–315. doi:10.1097/00042752-200409000-00018. PMID 15377972.
- ^ "Albuterol Sulfate", Rx List: The Internet Drug Index, 6/12/2008, retrieved 2014-07-13
Additional notes
- Moore, NG; Pegg, GG; Sillence, MN (September 1994). "Anabolic effects of the beta 2-adrenoceptor agonist salmeterol are dependent on route of administration". Am. J. Physiol. 267 (3 Pt 1): E475–84. PMID 7943228.
- Schiffelers, SL; Saris, WH; Boomsma, F; Van Baak, MA (May 2001). "beta(1)- and beta(2)-Adrenoceptor-mediated thermogenesis and lipid utilization in obese and lean men". J. Clin. Endocrinol. Metab. 86 (5): 2191–9. doi:10.1210/jc.86.5.2191. PMID 11344226.
- Van Baak, MA; Mayer, LH; Kempinski, RE; Hartgens, F (July 2000). "Effect of salbutamol on muscle strength and endurance performance in nonasthmatic men". Med Sci Sports Exerc 32 (7): 1300–6. doi:10.1097/00005768-200007000-00018. PMID 10912897.
- Caruso, JF; Hamill, JL; De Garmo, N (February 2005). "Oral albuterol dosing during the latter stages of a resistance exercise program". J Strength Cond Res 19 (1): 102–7. doi:10.1519/00124278-200502000-00018. PMID 15705021.
- Caruso JF, Signorile JF, Perry AC, et al. (November 1995). "The effects of albuterol and isokinetic exercise on the quadriceps muscle group". Med Sci Sports Exerc 27 (11): 1471–6. doi:10.1249/00005768-199511000-00002. PMID 8587482.
- Martineau, L; Horan, MA; Rothwell, NJ; Little, RA (November 1992). "Salbutamol, a beta 2-adrenoceptor agonist, increases skeletal muscle strength in young men". Clin. Sci. 83 (5): 615–21. PMID 1335400. S
- Desaphy, JF; Pierno, S; De Luca, A; Didonna, P; Camerino, DC (March 2003). "Different ability of clenbuterol and salbutamol to block sodium channels predicts their therapeutic use in muscle excitability disorders". Mol. Pharmacol. 63 (3): 659–70. doi:10.1124/mol.63.3.659. PMID 12606775.
- Maki, KC; Skorodin, MS; Jessen, JH; Laghi, F (June 1996). "Effects of oral albuterol on serum lipids and carbohydrate metabolism in healthy men". Metab. Clin. Exp. 45 (6): 712–7. doi:10.1016/S0026-0495(96)90136-5. PMID 8637445.
External links
- Salbutamol at The Periodic Table of Videos (University of Nottingham)
- Volmax Drug Information
- Side Effects
- U.S. National Library of Medicine: Drug Information Portal – Albuterol
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Adrenergics
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PNMT
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Catabolism
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MAO
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COMT
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- Entacapone
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Others
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Precursors
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- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
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Cofactors
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- Ferrous Iron (Fe2+)
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Others
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List of adrenergic drugs
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Drugs for obstructive airway diseases: asthma/COPD (R03)
|
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| Adrenergics, inhalants |
| Short acting β2-agonists |
- Bitolterol
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- Reproterol
- Rimiterol
- Salbutamol#/Levosalbutamol
- Terbutaline
- Tulobuterol
|
|
| Long acting β2-agonists (LABA) |
- Arformoterol
- Bambuterol
- Clenbuterol
- Formoterol
- Salmeterol
- Ultra LABA: Indacaterol, Olodaterol, Vilanterol
|
|
| other |
- Epinephrine#
- Hexoprenaline
- Isoprenaline (Isoproterenol)
- Orciprenaline (Metaproterenol)
|
|
|
| Glucocorticoids |
- Beclometasone#
- Betamethasone
- Budesonide
- Ciclesonide
- Flunisolide
- Fluticasone
- Mometasone
- Triamcinolone
|
|
Anticholinergics/
muscarinic antagonist |
- Aclidinium bromide
- Glycopyrronium bromide
- Ipratropium bromide#
- Oxitropium bromide
- Tiotropium bromide
- Umeclidinium bromide
|
|
| Mast cell stabilizers |
|
|
| Xanthines |
- Acefylline
- Ambuphylline
- Bamifylline
- Doxofylline
- Enprofylline
- Etamiphylline
- Proxyphylline
- Theobromine
- Theophylline/Aminophylline/Choline theophyllinate
|
|
| Eicosanoid inhibition |
| Leukotriene antagonists |
- Montelukast
- Pranlukast
- Zafirlukast
|
|
| Lipoxygenase inhibitor |
|
|
| Thromboxane receptor antagonists |
|
|
| Non-xanthine PDE4 inhibitors |
|
|
|
| Others/unknown |
- Amlexanox
- Eprozinol
- Fenspiride
- Omalizumab
|
|
| Combination products |
- Budesonide/formoterol
- Fluticasone/salmeterol
- Ipratropium bromide/salbutamol
- Mometasone/formoterol
- Beclometasone/formoterol
- Fluticasone furoate/vilanterol
- Umeclidinium bromide/vilanterol
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
anat (n, x, l, c)/phys/devp
|
noco (c, p)/cong/tumr, sysi/epon, injr
|
proc, drug (R1/2/3/5/6/7)
|
|
|
|
|
GlaxoSmithKline
|
|
| Subsidiaries |
- GlaxoSmithKline Pakistan
- GlaxoSmithKline Pharmaceuticals Ltd
- Stiefel Laboratories
- ViiV Healthcare (85%)
|
|
Predecessors and fully
integrated acquisitions |
- Allen & Hanburys
- Beecham Group
- Block Drug
- Burroughs Wellcome
- Glaxo
- Glaxo Wellcome
- Human Genome Sciences
- Recherche et Industrie Thérapeutiques
- SmithKline Beecham
- Smith, Kline & French
|
|
Products
(List) |
|
Current
|
|
Pharmaceuticals
|
- Advair
- Albenza
- Alli
- Amerge
- Amoxil
- Arixtra
- Arranon/Atriance
- Augmentin
- Avamys/Veramyst
- Avandia
- Avodart
- AZT1
- Beconase
- Boniva
- Ceftin/Supacef
- Combivir1
- Coreg
- Dexedrine
- Dyazide
- Epivir/Epivir-HBV/Heptovir/Zeffix1
- Flixonase
- Hycamtin
- Imitrex/Treximet
- Jalyn/Combodart/Duodart
- Lamictal
- Lanoxin
- Levitra2
- Lovaza/Omacor
- Parnate
- Paxil/Seroxat/Aropax
- Promacta/Revolade
- Relenza
- Requip
- Rescriptor1
- Serlipet
- Tagamet
- Treximet
- Trizivir1
- Tykerb/Tyverb
- Valtrex/Zelitrex
- Ventolin HFA
- Viracept1
- Wellbutrin
- Zantac
- Ziagen1
- Zofran
- Zovirax
|
|
|
Vaccines
|
- Hepatyrix
- Pandemrix
- Twinrix
|
|
|
Other
|
- Aquafresh
- Boost
- Eno
- Horlicks
- Maxinutrition
- Nicoderm
- Nicorette
- NiQuitin
- Panadol
- Panadol night
- Poligrip
- Ralgex
- Sensodyne
- Solpadeine
- Synthol
- Tums
|
|
|
|
Former
|
- BC Powder
- Geritol
- Goody's Powder
- Lucozade
- Ribena
|
|
|
| People |
|
Current directors
|
- Chris Gent
- Andrew Witty
- Roy Anderson
- Stephanie Burns
- Stacey Cartwright
- Lawrence Culp
- Crispin Davis
- Simon Dingemans
- Judy Lewent
- Deryck Maughan
- James Murdoch
- Daniel Podolsky
- Moncef Slaoui
- Tom de Swaan
- Robert Wilson
|
|
|
Other
|
- Thomas Beecham
- Silas M. Burroughs
- Mahlon Kline
- John K. Smith
- Henry Wellcome
|
|
|
| Other |
- Canada v. GlaxoSmithKline Inc.
- GlaxoSmithKline Prize
- Side Effects
- United States v. GlaxoSmithKline
|
|
- 1Products of ViiV Healthcare 2Co-marketed with Bayer Pharmaceuticals
|
|
