Bitolterol

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (RS)-[4-(1-Hydroxy-2-tert-butylamino-ethyl)-2-(4-methylbenzoyl)oxy-phenyl] 4-methylbenzoate

| image = Bitolterol.svg

| width = 240

| chirality = Racemic mixture

| tradename = Tornalate

| Drugs.com = {{drugs.com|CONS|bitolterol}}

| MedlinePlus = a601236

| pregnancy_category =

| legal_US = Discontinued

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| onset = 2–5 minutes

| elimination_half-life =

| duration_of_action = 6–8 hours

| CAS_number = 30392-40-6

| ATC_prefix = R03

| ATC_suffix = AC17

| ATC_supplemental =

| PubChem = 35330

| DrugBank = DB00901

| ChemSpiderID = 32525

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9KY0QXD6LI

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1201295

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07534

| index2_label = mesylate

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 30392-41-7

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 4E53T3611U

| KEGG2_Ref = {{keggcite|correct|kegg}}

| KEGG2 = D00684

| C = 28

| H = 31

| N = 1

| O = 5

| smiles = O=C(Oc2cc(ccc2OC(=O)c1ccc(cc1)C)C(O)CNC(C)(C)C)c3ccc(cc3)C

}}

Bitolterol mesylate, formerly sold under the brand name Tornalate, is a short-acting β₂-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma{{cite journal | vauthors = 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 = Annals of Allergy | volume = 56 | issue = 6 | pages = 494–499 | date = June 1986 | pmid = 3717716 }}{{cite journal | vauthors = Nathan RA, Bernstein IL, Bronsky EA, Bush RK, Chervinsky P, Condemi JJ, Dockhorn RJ, Pinnas JL, Repsher LH | display-authors = 6 | title = Comparison of the bronchodilator effects of nebulized bitolterol mesylate and isoproterenol hydrochloride in steroid-dependent asthma | journal = The Journal of Allergy and Clinical Immunology | volume = 79 | issue = 5 | pages = 822–829 | date = May 1987 | pmid = 3571773 | doi = 10.1016/0091-6749(87)90216-8 | doi-access = free }} and chronic obstructive pulmonary disease (COPD).{{cite journal | vauthors = Friedel HA, Brogden RN | title = Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease | journal = Drugs | volume = 35 | issue = 1 | pages = 22–41 | date = January 1988 | pmid = 3278878 | doi = 10.2165/00003495-198835010-00002 | url = http://ukpmc.ac.uk/abstract/MED/3278878/reload=0;jsessionid=c0HU7QxJoemJjpllzd68.24 | url-status = dead | s2cid = 218471864 | archive-url = https://archive.today/20121223091149/http://ukpmc.ac.uk/abstract/MED/3278878/reload=0;jsessionid=c0HU7QxJoemJjpllzd68.24 | archive-date = 2012-12-23 }}{{cite journal | vauthors = | title = Early Career Awards for 1978 (John Robert Anderson, Philip M. Groves, Gary E. Schwartz) | journal = The American Psychologist | volume = 34 | issue = 1 | pages = 69–79 | date = January 1979 | pmid = 396832 | doi = 10.1037/h0078247 }}{{cite journal | vauthors = Petty TL, Scoggin CH, Rollins DR, Repsher LH | title = Bitolterol compared to isoproterenol in advanced chronic obstructive pulmonary disease | journal = Chest | volume = 86 | issue = 3 | pages = 404–408 | date = September 1984 | pmid = 6380974 | doi = 10.1378/chest.86.3.404 }} Bitolterol relaxes the smooth muscles present continuously around the bronchi and bronchioles facilitating the flow of air through them.

File:Colterol.svg]]

Bitolterol is a prodrug of colterol.{{cite journal | vauthors = Walker SB, Kradjan WA, Bierman CW | title = Bitolterol mesylate: a beta-adrenergic agent. Chemistry, pharmacokinetics, pharmacodynamics, adverse effects and clinical efficacy in asthma | journal = Pharmacotherapy | volume = 5 | issue = 3 | pages = 127–137 | date = 6 May 1985 | pmid = 3895171 | doi = 10.1002/j.1875-9114.1985.tb03410.x | s2cid = 29431526 }}{{cite web|title=ChEBI: Bitolterol|url=http://www.ebi.ac.uk/chebi/searchId.do?chebiId=3133|website=Chemical Entities of Biological Interest|publisher=Wellcome Genome Campus, Hinxton, Cambridgeshire, CB10 1SD, UK|access-date=27 March 2016}} It has a rapid onset of action (2–5 minutes) and may last up to 6–8 hours.{{cite journal | vauthors = Kass I, Mingo TS | title = Bitolterol mesylate (WIN 32784) aerosol. A new long-acting bronchodilator with reduced chronotropic effects | journal = Chest | volume = 78 | issue = 2 | pages = 283–287 | date = August 1980 | pmid = 6995040 | doi = 10.1378/chest.78.2.283 }}

The drug, alone or in co-administration with theophylline, doesn't show cardiotoxic effect.{{cite journal | vauthors = Kemp JP, Chervinsky P, Orgel HA, Meltzer EO, Noyes JH, Mingo TS | title = Concomitant bitolterol mesylate aerosol and theophylline for asthma therapy, with 24 hr electrocardiographic monitoring | journal = The Journal of Allergy and Clinical Immunology | volume = 73 | issue = 1 Pt 1 | pages = 32–43 | date = January 1984 | pmid = 6693665 | doi = 10.1016/0091-6749(84)90481-0 | doi-access = free }}

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

{{clear left}}