Chemistry:Bitolterol

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Short description: Chemical compound
Bitolterol
Bitolterol.svg
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601236
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC28H31NO5
Molar mass461.558 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture

Bitolterol mesylate (Tornalate) is a short-acting β2 adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma[1][2] and COPD.[3][4][5] In these disorders there is a narrowing of the airways (bronchi and their ramifications) that carry air to the lungs. Muscle spasm and inflammation within the bronchi worsen this narrowing. Bitolterol relaxes the smooth muscles present continuously around the bronchi and bronchioles facilitating the flow of air through them.

Bitolterol is a prodrug of colterol.[6][7] It has a rapid onset of action (2–5 minutes) and may last up to 6–8 hours.[8] The drug, alone or in co-administration with theophylline, doesn't show cardiotoxic effect.[9]

The U.S. Food and Drug Administration (FDA) approved bitolterol in December 1984. The drug was withdrawn from the market by Élan Pharmaceuticals in 2001.

References

  1. "Bitolterol mesylate aerosol in adults with steroid-dependent asthma: a comparison with isoproterenol hydrochloride aerosol". Annals of Allergy 56 (6): 494–499. June 1986. PMID 3717716. 
  2. "Comparison of the bronchodilator effects of nebulized bitolterol mesylate and isoproterenol hydrochloride in steroid-dependent asthma". The Journal of Allergy and Clinical Immunology 79 (5): 822–829. May 1987. doi:10.1016/0091-6749(87)90216-8. PMID 3571773. 
  3. "Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease". Drugs 35 (1): 22–41. January 1988. doi:10.2165/00003495-198835010-00002. PMID 3278878. http://ukpmc.ac.uk/abstract/MED/3278878/reload=0;jsessionid=c0HU7QxJoemJjpllzd68.24. 
  4. "Early Career Awards for 1978 (John Robert Anderson, Philip M. Groves, Gary E. Schwartz)". The American Psychologist 34 (1): 69–79. January 1979. doi:10.1037/h0078247. PMID 396832. 
  5. "Bitolterol compared to isoproterenol in advanced chronic obstructive pulmonary disease". Chest 86 (3): 404–408. September 1984. doi:10.1378/chest.86.3.404. PMID 6380974. 
  6. "Bitolterol mesylate: a beta-adrenergic agent. Chemistry, pharmacokinetics, pharmacodynamics, adverse effects and clinical efficacy in asthma". Pharmacotherapy 5 (3): 127–137. 6 May 1985. doi:10.1002/j.1875-9114.1985.tb03410.x. PMID 3895171. 
  7. "ChEBI: Bitolterol". Wellcome Genome Campus, Hinxton, Cambridgeshire, CB10 1SD, UK. http://www.ebi.ac.uk/chebi/searchId.do?chebiId=3133. 
  8. "Bitolterol mesylate (WIN 32784) aerosol. A new long-acting bronchodilator with reduced chronotropic effects". Chest 78 (2): 283–287. August 1980. doi:10.1378/chest.78.2.283. PMID 6995040. 
  9. "Concomitant bitolterol mesylate aerosol and theophylline for asthma therapy, with 24 hr electrocardiographic monitoring". The Journal of Allergy and Clinical Immunology 73 (1 Pt 1): 32–43. January 1984. doi:10.1016/0091-6749(84)90481-0. PMID 6693665.