French
DeutschBambuterol
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 Bambuterol (top), and (R)-bambuterol (bottom) | |
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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 | Extensive hepatic. Further metabolized to terbutaline by plasma cholinesterase |
| Elimination half-life | 13 hours (bambuterol) 21 hours (terbutaline) |
| Excretion | Renal |
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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 a long-acting β adrenoceptor agonist (LABA) used in the treatment of asthma; it also is a prodrug of terbutaline. Commercially, the AstraZeneca pharmaceutical company produces and markets bambuterol as Bambec and Oxeol.[1]
It is not available in the U.S.
Indications
[edit]As other LABAs, bambuterol is used in the long-term management of persistent asthma.[1] It should not be used as a rescue medication for short-term relief of asthma symptoms.
Contraindications
[edit]Bambuterol is contraindicated in pregnancy and in people with seriously impaired liver function. It can be used by people with renal impairment, but dose adjustments are necessary.[1]
Adverse effects
[edit]The adverse effect profile of bambuterol is similar to that of salbutamol, and may include fatigue, nausea, palpitations, headache, dizziness and tremor.[1]
Interactions
[edit]Concomitant administration of bambuterol with corticosteroids, diuretics, and xanthine derivatives (such as theophylline) increases the risk of hypokalemia (decreased levels of potassium in the blood).[2]
Bambuterol acts as a cholinesterase inhibitor, and can prolong the duration of action of suxamethonium (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 of non-depolarizing neuromuscular blockers, such as vecuronium bromide.[2]
Synthesis
[edit]
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).
References
[edit]- ^ a b c d e Sweetman SC, ed. (2009). "Bronchodilators and Anti-asthma Drugs". Martindale: The complete drug reference (36th ed.). London: Pharmaceutical Press. pp. 1115–16. ISBN 978-0-85369-840-1.
- ^ a b Sweetman (2009), pp. 1132–33.
- ^ Sitar DS (October 1996). "Clinical pharmacokinetics of bambuterol". Clinical Pharmacokinetics. 31 (4): 246–56. doi:10.2165/00003088-199631040-00002. PMID 8896942. S2CID 25696134.
- ^ Castaer, J.; Prous, J.; Bambuterol. Drugs Fut 1986, 11, 7, 553.
- ^ EP0043807 idem Otto Agne Olsson, et al. U.S. patent 4,419,364 (1983 to DRACO AB); CA, 96, 199263.
- ^ 김신종, et al. KR100803291 (2008).
- ^ 唐冬军 & 寇景平, CN104262202 (2016 to Guangdong HEC Pharmaceutical).
- ^ Asami, K., Machida, T., Jung, S., Hanaya, K., Shoji, M., Sugai, T. (December 2013). "Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with incubated whole cells of Williopsis californica JCM 3600". Journal of Molecular Catalysis B: Enzymatic. 97: 106–109. doi:10.1016/j.molcatb.2013.08.003.
- ^ Cao, G., Hu, A., Zou, K., Xu, L., Chen, J., Tan, W. (July 2008). "Highly enantioselective synthesis, crystal structure, and circular dichroism spectroscopy of ( R )-bambuterol hydrochloride". Chirality. 20 (7): 856–862. doi:10.1002/chir.20558.