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 Bambuterol (top), and (R)-bambuterol (bottom) | |
| Clinical data | |
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| AHFS/Drugs.com | International Drug Names |
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| Routes of administration | Oral (tablets) |
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| Pharmacokinetic data | |
| Bioavailability | 20% |
| Metabolism | Extensivehepatic. Further metabolized toterbutaline by plasmacholinesterase |
| Eliminationhalf-life | 13 hours (bambuterol) 21 hours (terbutaline) |
| Excretion | Renal |
| Identifiers | |
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| Chemical and physical data | |
| Formula | C18H29N3O5 |
| Molar mass | 367.446 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
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Bambuterol (INN) is along-acting β adrenoceptor agonist (LABA) used in the treatment ofasthma; it also is aprodrug ofterbutaline. Commercially, theAstraZeneca pharmaceutical company produces and markets bambuterol asBambec andOxeol.[1]
It is not available in the U.S.
As other LABAs, bambuterol is used in the long-term management of persistentasthma.[1] It should not be used as a rescue medication for short-term relief of asthma symptoms.
Bambuterol is contraindicated in pregnancy and in people with seriouslyimpaired liver function. It can be used by people withrenal impairment, but dose adjustments are necessary.[1]
The adverse effect profile of bambuterol is similar to that ofsalbutamol, and may includefatigue,nausea,palpitations,headache,dizziness andtremor.[1]
Concomitant administration of bambuterol withcorticosteroids,diuretics, andxanthine derivatives (such astheophylline) increases the risk ofhypokalemia (decreased levels ofpotassium in the blood).[2]
Bambuterol acts as acholinesterase inhibitor, and can prolong the duration of action ofsuxamethonium (succinylcholine) and other drugs whose breakdown in the body depends on cholinesterase function.[1] Butyrylcholinesterase activity returns to normal approximately two weeks after bambuterol is stopped.[3] It can also enhance the effects ofnon-depolarizingneuromuscular blockers, such asvecuronium bromide.[2]
The reaction between 3',5'-Dihydroxyacetophenone [51863-60-6] (1) and Dimethylcarbamoyl chloride [79-44-7] (2) gives 5-Acetyl-1,3-phenylene bis(dimethylcarbamate) [81732-48-1] (3). Halogenation with bromine led to 5-(Bromoacetyl)-1,3-phenylene bis(dimethylcarbamate) [81732-49-2] (4). Treatment with N-(tert-Butyl)benzylamine [3378-72-1] (5) afforded [81732-47-0] (6). Catalytic hydrogenation completed the synthesis of bambuterol (7).
