Bitolterol: Difference between revisions

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{{drugbox
{{Drugbox
| IUPAC_name = [4-(1-hydroxy-2-tert-butylamino-ethyl)- 2-(4-methylbenzoyl)oxy-phenyl] 4-methylbenzoate
| IUPAC_name = (''RS'')-[4-(1-Hydroxy-2-''tert''-butylamino-ethyl)-2-(4-methylbenzoyl)oxy-phenyl] 4-methylbenzoate
| image = Bitolterol.png
| image = Bitolterol.png
| width = 200px
| imagename = 1 : 1 mixture (racemate)
| drug_name = Bitolterol.png
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|CONS|bitolterol}}
| MedlinePlus = a601236
| pregnancy_category = 
| legal_status = 
| routes_of_administration = 
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
<!--Identifiers-->
| CAS_number = 30392-41-7
| CAS_number = 30392-41-7
| ATC_prefix = R03
| ATC_prefix = R03
| ATC_suffix = AC17
| ATC_suffix = AC17
| ATC_supplemental =  
| ATC_supplemental =
| PubChem = 35330
| PubChem = 35330
| DrugBank = APRD00827
| DrugBank = DB00901
| C=28 | H=31 | N=1 | O=5
| ChemSpiderID = 32525
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9KY0QXD6LI
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1201295
 
<!--Chemical data-->
| C=28 | H=31 | N=1 | O=5  
| molecular_weight = 461.549 g/mol
| molecular_weight = 461.549 g/mol
| bioavailability =  
| smiles = O=C(Oc2cc(ccc2OC(=O)c1ccc(cc1)C)C(O)CNC(C)(C)C)c3ccc(cc3)C
| protein_bound =  
| InChI = 1/C28H31NO5/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21/h6-16,23,29-30H,17H2,1-5H3
| metabolism =  
| InChIKey = FZGVEKPRDOIXJY-UHFFFAOYAR
| elimination_half-life =
| pregnancy_category =
| legal_status =
| routes_of_administration =  
}}
}}
 
__NOTOC__
{{SI}}
{{SI}}
{{EH}}
{{CMG}}
 
==Overview==
==Overview==
'''Bitolterol mesylate''' (Tornalate®) is a [[beta2-adrenergic receptor agonist|β<sub>2</sub>-adrenergic receptor agonist]] used for the relief of [[bronchospasm]] in conditions such as [[asthma]] and [[COPD]].   
'''Bitolterol mesylate''' (Tornalate) is a [[beta2-adrenergic receptor agonist|β<sub>2</sub>-adrenergic receptor agonist]] used for the relief of [[bronchospasm]] in conditions such as [[asthma]]<ref name="pmid3717716">{{cite journal |author=Nathan RA, Bodman SF, Storms WW, Mingo TS |title=Bitolterol mesylate aerosol in adults with steroid-dependent asthma: a comparison with isoproterenol hydrochloride aerosol |journal=Ann Allergy |volume=56 |issue=6 |pages=494–9 |date=June 1986 |pmid=3717716 |doi= |url=}}</ref><ref name="pmid3571773">{{cite journal |author=Nathan RA, Bernstein IL, Bronsky EA, Bush RK, Chervinsky P, Condemi JJ, Dockhorn RJ, Pinnas JL, Repsher LH |title=Comparison of the bronchodilator effects of nebulized bitolterol mesylate and isoproterenol hydrochloride in steroid-dependent asthma |journal=J. Allergy Clin. Immunol. |volume=79 |issue=5 |pages=822–9 |date=May 1987 |pmid=3571773 |doi= 10.1016/0091-6749(87)90216-8|url=}}</ref> and [[Chronic obstructive pulmonary disease|COPD]].<ref>{{cite journal|author1=Friedel HA |author2=Brogden RN |title=Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease|journal= Drugs |year =1988 |volume = 35 |pages = 22–41 |url = http://ukpmc.ac.uk/abstract/MED/3278878/reload=0;jsessionid=c0HU7QxJoemJjpllzd68.24 |doi=10.2165/00003495-198835010-00002}}</ref><ref name="Anderson-1979">{{Cite journal  | last1 = Anderson | first1 = JR. | last2 = Groves | first2 = PM. | last3 = Schwartz | first3 = GE. | title = Early Career Awards for 1978 (John Robert Anderson, Philip M. Groves, Gary E. Schwartz). | journal = Am Psychol | volume = 34 | issue = 1 | pages = 69-79 |date=Jan 1979 | doi = | PMID = 396832 }}</ref><ref name="Petty-1984">{{Cite journal  | last1 = Petty | first1 = TL. | last2 = Scoggin | first2 = CH. | last3 = Rollins | first3 = DR. | last4 = Repsher | first4 = LH. | title = Bitolterol compared to isoproterenol in advanced chronic obstructive pulmonary disease. | journal = Chest | volume = 86 | issue = 3 | pages = 404-8 |date=Sep 1984 | doi =  10.1378/chest.86.3.404| PMID = 6380974 }}</ref> 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 get worse this narrowing. Bitolterol relaxes the smooth muscles  present continuously around the bronchi and bronchioles facilitating the flow of air through them.


Bitolterol has a rapid onset of action (2-5 minutes) and may last up to 6-8 hours.
Bitolterol has a rapid onset of action (2&ndash;5 minutes) and may last up to 6&ndash;8 hours.<ref name="pmid6995040">{{Cite journal  | last1 = Kass | first1 = I. | last2 = Mingo | first2 = TS. | title = Bitolterol mesylate (WIN 32784) aerosol. A new long-acting bronchodilator with reduced chronotropic effects. | journal = Chest | volume = 78 | issue = 2 | pages = 283-7 |date=Aug 1980 | doi =  10.1378/chest.78.2.283| PMID = 6995040 }}</ref>
The drug, alone or in co-administration with theophylline, doesn't show cardiotoxic effect.<ref name="pmid6693665">{{Cite journal  | last1 = Kemp | first1 = JP. | last2 = Chervinsky | first2 = P. | last3 = Orgel | first3 = HA. | last4 = Meltzer | first4 = EO. | last5 = Noyes | first5 = JH. | last6 = Mingo | first6 = TS. | title = Concomitant bitolterol mesylate aerosol and theophylline for asthma therapy, with 24 hr electrocardiographic monitoring. | journal = J Allergy Clin Immunol | volume = 73 | issue = 1 Pt 1 | pages = 32-43 |date=Jan 1984 | doi =  10.1016/0091-6749(84)90481-0| PMID = 6693665 }}</ref> 


Bitolterol was withdrawn from the market by [[Élan|Élan Pharmaceuticals]] in 2001.
The USA [[Food and Drug Administration]] (FDA) approved bitolterol in December 1984. The drug was withdrawn from the market by [[Élan|Élan Pharmaceuticals]] in 2001.


{{SIB}}
== References ==
{{Reflist|2}}


[[Category:Asthma]]
{{Adrenergic agonists}}
[[Category:Pulmonology]]
{{Asthma_and_copd_rx}}


{{WikiDoc Help Menu}}
[[Category:Beta-adrenergic agonists]]
{{WS}}
[[Category:Benzoates]]
[[Category:Drug]]

Latest revision as of 18:11, 18 August 2015

Bitolterol.png
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601236
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC28H31NO5
Molar mass461.549 g/mol
3D model (JSmol)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Bitolterol mesylate (Tornalate) is a 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 get worse this narrowing. Bitolterol relaxes the smooth muscles present continuously around the bronchi and bronchioles facilitating the flow of air through them.

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

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

References

  1. ↑ Nathan RA, Bodman SF, Storms WW, Mingo TS (June 1986). "Bitolterol mesylate aerosol in adults with steroid-dependent asthma: a comparison with isoproterenol hydrochloride aerosol". Ann Allergy. 56 (6): 494–9. PMID 3717716.
  2. ↑ Nathan RA, Bernstein IL, Bronsky EA, Bush RK, Chervinsky P, Condemi JJ, Dockhorn RJ, Pinnas JL, Repsher LH (May 1987). "Comparison of the bronchodilator effects of nebulized bitolterol mesylate and isoproterenol hydrochloride in steroid-dependent asthma". J. Allergy Clin. Immunol. 79 (5): 822–9. doi:10.1016/0091-6749(87)90216-8. PMID 3571773.
  3. ↑ Friedel HA; Brogden RN (1988). "Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease". Drugs. 35: 22–41. doi:10.2165/00003495-198835010-00002.
  4. ↑ Anderson, JR.; Groves, PM.; Schwartz, GE. (Jan 1979). "Early Career Awards for 1978 (John Robert Anderson, Philip M. Groves, Gary E. Schwartz)". Am Psychol. 34 (1): 69–79. PMID 396832.
  5. ↑ Petty, TL.; Scoggin, CH.; Rollins, DR.; Repsher, LH. (Sep 1984). "Bitolterol compared to isoproterenol in advanced chronic obstructive pulmonary disease". Chest. 86 (3): 404–8. doi:10.1378/chest.86.3.404. PMID 6380974.
  6. ↑ Kass, I.; Mingo, TS. (Aug 1980). "Bitolterol mesylate (WIN 32784) aerosol. A new long-acting bronchodilator with reduced chronotropic effects". Chest. 78 (2): 283–7. doi:10.1378/chest.78.2.283. PMID 6995040.
  7. ↑ Kemp, JP.; Chervinsky, P.; Orgel, HA.; Meltzer, EO.; Noyes, JH.; Mingo, TS. (Jan 1984). "Concomitant bitolterol mesylate aerosol and theophylline for asthma therapy, with 24 hr electrocardiographic monitoring". J Allergy Clin Immunol. 73 (1 Pt 1): 32–43. doi:10.1016/0091-6749(84)90481-0. PMID 6693665.

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