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Bambuterol

July 24, 2017
Common Name

Bambuterol Description

Bambuterol is only found in individuals that have used or taken this drug. It is a long acting beta-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline.The pharmacologic effects of bambuterol are at least in part attributable to stimliation through beta-adrenergic receptors (beta 2 receptors) of intracellliar 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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+-)-5-(2-(Tert-butylamino)-1-hydroxyethyl)-m-phenylene bis(dimethylcarbamate)ChEBI BambuterolumChEBI Terbutaline bis(dimethylcarbamate)ChEBI Terbutaline bisdimethylcarbamateChEBI (+-)-5-(2-(Tert-butylamino)-1-hydroxyethyl)-m-phenylene bis(dimethylcarbamic acid)Generator Terbutaline bis(dimethylcarbamic acid)Generator Terbutaline bisdimethylcarbamic acidGenerator Bambuterol hydrochlorideHMDB 5-(2-(Tert-butylamino)-1-hydroxyethyl)-3-phenylene bis(dimethylcarbamate)MeSH

Chemical Formlia

C18H29N3O5 Average Molecliar Weight

367.44 Monoisotopic Molecliar Weight

367.210721053 IUPAC Name

3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate Traditional Name

bambuterol CAS Registry Number

81732-46-9 SMILES

CN(C)C(=O)OC1=CC(=CC(OC(=O)N(C)C)=C1)C(O)CNC(C)(C)C

InChI Identifier

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

InChI Key

ANZXOIAKUNOVQU-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Phenoxy compounds Alternative Parents

  • Aralkylamines
  • Carbamate esters
  • Secondary alcohols
  • 1,2-aminoalcohols
  • Dialkylamines
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Aromatic alcohols

    • Substituents

  • Phenoxy compound
  • Aralkylamine
  • Carbamic acid ester
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • carbamate ester (CHEBI:553827 )
  • phenylethanolamines (CHEBI:553827 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic beta-Agonists
  • Bronchodilator Agents
  • Sympathomimetics
  • Tocolytic Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility4.69e-01 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.47 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01408

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01408

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01408 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    49466 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Bambuterol NuGOwiki Link

    HMDB15478 Metagene Link

    HMDB15478 METLIN ID

    Not Available PubChem Compound

    54766 PDB ID

    Not Available ChEBI ID

    553827

    Product: Zaltoprofen

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in carboxylesterase activity
    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
    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 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    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:
    46458.3
    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 rats 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 ]

    PMID: 24176114

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