Bambuterol

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Bambuterol
Bambuterol.svg
Bambuterol ball-and-stick model.png
Bambuterol (top),
and (R)-bambuterol (bottom)
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Unknown
Routes of
administration
Oral (tablets)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20%
MetabolismExtensive hepatic.
Further metabolized to terbutaline by plasma cholinesterase
Elimination half-life13 hours (bambuterol)
21 hours (terbutaline)
ExcretionRenal
Identifiers
  • (RS)-5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diyl bis(dimethylcarbamate)
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H29N3O5
Molar mass367.446 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C(Oc1cc(cc(OC(=O)N(C)C)c1)C(O)CNC(C)(C)C)N(C)C
  • InChI=1S/C18H29N3O5/c1-18(2,3)19-11-15(22)12-8-13(25-16(23)20(4)5)10-14(9-12)26-17(24)21(6)7/h8-10,15,19,22H,11H2,1-7H3 checkY
  • Key:ANZXOIAKUNOVQU-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

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

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

The adverse effect profile of bambuterol is similar to that of salbutamol, and may include fatigue, nausea, palpitations, headache, dizziness and tremor.[1]

Interactions

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]

References

  1. ^ 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.
  2. ^ a b Sweetman (2009), pp. 1132–33.
  3. ^ Sitar DS (October 1996). "Clinical pharmacokinetics of bambuterol". Clinical Pharmacokinetics. 31 (4): 246–56. doi:10.2165/00003088-199631040-00002. PMID 8896942.