Bambuterol

Chemical compound

Unknown

Routes of
administrationOral (tablets)ATC code

R03CC12 (WHO)

AU: S4 (Prescription only)
In general: ℞ (Prescription only)

Pharmacokinetic dataBioavailability20%MetabolismExtensive hepatic.
Further metabolized to terbutaline by plasma cholinesteraseElimination half-life13 hours (bambuterol)
21 hours (terbutaline)ExcretionRenalIdentifiers

IUPAC name

(RS)-5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diyl bis(dimethylcarbamate)

CAS Number

81732-65-2^Y
HCl: 81732-46-9^Y

PubChem CID

54766

IUPHAR/BPS

6601

DrugBank

DB01408^N

ChemSpider

49466^Y

UNII

Y1850G1OVC
HCl: 786Q84QZ3F^Y

KEGG

D07377^Y

ChEBI

CHEBI:553827^N

ChEMBL

ChEMBL521589^Y

CompTox Dashboard (EPA)

DTXSID5048550

Chemical and physical dataFormulaC₁₈H₂₉N₃O₅Molar mass367.446 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic mixture

SMILES

O=C(Oc1cc(cc(OC(=O)N(C)C)c1)C(O)CNC(C)(C)C)N(C)C

InChI

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^Y
Key:ANZXOIAKUNOVQU-UHFFFAOYSA-N^Y

^NY (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

^ ^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.

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol
Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast