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Identification
NameBambuterol
Accession NumberDB01408
TypeSmall Molecule
GroupsApproved
Description

Bambuterol is a long acting beta-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline.

Structure
Thumb
Synonyms
(±)-5-(2-(tert-butylamino)-1-hydroxyethyl)-m-phenylene bis(dimethylcarbamate)
bambutérol
Bambuterol
Bambuterolum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BambecNot Available
OxeolNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Bambuterol hydrochloride
81732-46-9
Thumb
  • InChI Key: LBARATORRVNNQM-UHFFFAOYSA-N
  • Monoisotopic Mass: 403.187398792
  • Average Mass: 403.901
DBSALT000797
Categories
UNIIY1850G1OVC
CAS number81732-65-2
WeightAverage: 367.44
Monoisotopic: 367.210721053
Chemical FormulaC18H29N3O5
InChI KeyInChIKey=ANZXOIAKUNOVQU-UHFFFAOYSA-N
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
IUPAC Name
3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate
SMILES
CN(C)C(=O)OC1=CC(=CC(OC(=O)N(C)C)=C1)C(O)CNC(C)(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the prevention and reversal of bronchospasm in patients 12 years of age and older with asthma and reversible bronchospasm associated with bronchitis and emphysema.
PharmacodynamicsBambuterol is a long acting beta2-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline. Bambuterol causes smooth muscle relaxation, resulting in dilation of bronchial passages.
Mechanism of actionThe pharmacologic effects of bambuterol are at least in part attributable to stimulation through beta-adrenergic receptors (beta 2 receptors) of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
Related Articles
AbsorptionBioavailability is 20% following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic, extensive. Further metabolized to terbutaline by plasma cholinesterase.

SubstrateEnzymesProduct
Bambuterol
terbutalineDetails
Route of eliminationNot Available
Half life13 hours for bambuterol and 21 hours for the primary active metabolite terbutaline.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8638
Blood Brain Barrier-0.761
Caco-2 permeable-0.6746
P-glycoprotein substrateSubstrate0.7076
P-glycoprotein inhibitor INon-inhibitor0.8708
P-glycoprotein inhibitor IINon-inhibitor0.8921
Renal organic cation transporterNon-inhibitor0.9451
CYP450 2C9 substrateNon-substrate0.7745
CYP450 2D6 substrateNon-substrate0.8167
CYP450 3A4 substrateNon-substrate0.5157
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9155
CYP450 2D6 inhibitorInhibitor0.8689
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.927
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9738
Ames testNon AMES toxic0.7909
CarcinogenicityNon-carcinogens0.762
BiodegradationNot ready biodegradable0.9963
Rat acute toxicity2.5730 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9727
hERG inhibition (predictor II)Non-inhibitor0.937
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.469 mg/mLALOGPS
logP1.69ALOGPS
logP1.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.34 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity98.28 m3·mol-1ChemAxon
Polarizability40.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Peter Jaksch, “Method of preparing an intermediate for the manufacture of bambuterol.” U.S. Patent US5200551, issued May, 1986.

US5200551
General ReferencesNot Available
External Links
ATC CodesR03CC12
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
SuccinylcholineThe therapeutic efficacy of Succinylcholine can be increased when used in combination with Bambuterol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Rosberg B, Schroder C, Nyberg L, Rosenborg J, Wiren JE: Bambuterol and terbutaline in human cerebrospinal fluid and plasma. Eur J Clin Pharmacol. 1993;45(2):147-50. [PubMed:8223836 ]
  2. Svensson LA: Bambuterol, a bronchodilator prodrug with sustained action, enhances delivery of active drug to the lung. Agents Actions Suppl. 1988;23:271-6. [PubMed:3262993 ]
  3. Waldeck B: Beta-adrenoceptor agonists and asthma--100 years of development. Eur J Pharmacol. 2002 Jun 7;445(1-2):1-12. [PubMed:12065188 ]
  4. Coleman RA, Johnson M, Nials AT, Vardey CJ: Exosites: their current status, and their relevance to the duration of action of long-acting beta 2-adrenoceptor agonists. Trends Pharmacol Sci. 1996 Sep;17(9):324-30. [PubMed:8885698 ]
  5. Zhang D, Cheng M, Hyun MH, Xiong Z, Pan L, Li F: Enantiomeric separation of beta2-agonists on macrocyclic antibiotic chiral stationary phases in high performance liquid chromatography. Pharmazie. 2007 Nov;62(11):836-40. [PubMed:18065099 ]
  6. Chou YL, Wu CC, Wang HW: Effects of bambuterol and terbutaline on isolated rat's tracheal smooth muscle. Eur Arch Otorhinolaryngol. 2010 Aug;267(8):1305-11. doi: 10.1007/s00405-009-1173-7. Epub 2009 Dec 12. [PubMed:20012638 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Gazic I, Bosak A, Sinko G, Vinkovic V, Kovarik Z: Preparative HPLC separation of bambuterol enantiomers and stereoselective inhibition of human cholinesterases. Anal Bioanal Chem. 2006 Aug;385(8):1513-9. Epub 2006 Jul 25. [PubMed:16865342 ]
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Drug created on July 17, 2007 06:34 / Updated on August 17, 2016 12:23