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    Bambuterol Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

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    $ API Ref.Price (USD/KG) : 596Xls

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    2D Structure
    Also known as: 81732-65-2, Bambec, Bambuterolum, Bambuterol (inn), Chebi:553827, [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(dimethylcarbamoyloxy)phenyl] n,n-dimethylcarbamate
    Molecular Formula
    C18H29N3O5
    Molecular Weight
    367.4  g/mol
    InChI Key
    ANZXOIAKUNOVQU-UHFFFAOYSA-N
    FDA UNII
    Y1850G1OVC
    Bambuterol is a long acting beta-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(dimethylcarbamoyloxy)phenyl] N,N-dimethylcarbamate
    2.1.2 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
    2.1.3 InChI Key
    ANZXOIAKUNOVQU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)NCC(C1=CC(=CC(=C1)OC(=O)N(C)C)OC(=O)N(C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    Y1850G1OVC
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-(2-(tert-butylamino)-1-hydroxyethyl)-3-phenylene Bis(dimethylcarbamate)

    2. Bambuterol Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 81732-65-2

    2. Bambec

    3. Bambuterolum

    4. Bambuterol (inn)

    5. Chebi:553827

    6. [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(dimethylcarbamoyloxy)phenyl] N,n-dimethylcarbamate

    7. Y1850g1ovc

    8. (+/-)-bambuterol;kwd-2183

    9. (+-)-5-(2-(tert-butylamino)-1-hydroxyethyl)-m-phenylene Bis(dimethylcarbamate)

    10. Bambuterolum [latin]

    11. Oxeol

    12. Bambuterol [inn]

    13. Kwd-2183

    14. 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diyl Bis(dimethylcarbamate)

    15. (+/-)-5-(2-(tert-butylamino)-1-hydroxyethyl)-m-phenylene Bis(dimethylcarbamate)

    16. Terbutaline Bisdimethylcarbamate

    17. Bambuterol [inn:ban]

    18. Unii-y1850g1ovc

    19. Terbutaline Bis(dimethylcarbamate)

    20. Bambuterol [mi]

    21. Prestwick0_000361

    22. Prestwick1_000361

    23. Prestwick2_000361

    24. Prestwick3_000361

    25. Schembl4431

    26. Bambuterol [who-dd]

    27. Bspbio_000481

    28. Mls002153785

    29. Spbio_002402

    30. Bpbio1_000531

    31. Chembl521589

    32. Gtpl6601

    33. Dtxsid5048550

    34. Glxc-25236

    35. Hms2089j18

    36. Hms2230o15

    37. Hms3373n13

    38. Bcp21793

    39. Bdbm50235800

    40. Stk643808

    41. Akos005574764

    42. Cs-3157

    43. Db01408

    44. ( Inverted Exclamation Marka)-bambutero

    45. ( Inverted Exclamation Marka)-bambuterol

    46. Ncgc00179546-01

    47. Ncgc00179546-02

    48. Ac-35438

    49. Hy-17501

    50. Smr001233168

    51. Sbi-0207028.p001

    52. Ft-0602901

    53. D07377

    54. 732b652

    55. A840189

    56. L004435

    57. Q3633651

    58. Sr-05000001470-1

    59. Brd-a17462676-003-03-3

    60. Brd-a17462676-003-06-6

    61. (rs)-5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diyl Bis(dimethylcarbamate)

    62. 5-(2-(tert-butylamino)-1-hydroxyethyl)-1,3-phenylene Bis(dimethylcarbamate)

    63. [3-[2-(tert-butylamino)-1-oxidanyl-ethyl]-5-(dimethylcarbamoyloxy)phenyl] N,n-dimethylcarbamate

    64. N,n-dimethylcarbamic Acid [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[dimethylamino(oxo)methoxy]phenyl] Ester

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 367.4 g/mol
    Molecular Formula C18H29N3O5
    XLogP31.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count8
    Exact Mass367.21072103 g/mol
    Monoisotopic Mass367.21072103 g/mol
    Topological Polar Surface Area91.3 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity446
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the prevention and reversal of bronchospasm in patients 12 years of age and older with asthma and reversible bronchospasm associated with bronchitis and emphysema.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Bambuterol 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.

    5.2 MeSH Pharmacological Classification

    Bronchodilator Agents

    Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

    5.3 ATC Code

    R - Respiratory system

    R03 - Drugs for obstructive airway diseases

    R03C - Adrenergics for systemic use

    R03CC - Selective beta-2-adrenoreceptor agonists

    R03CC12 - Bambuterol

    5.4 Absorption, Distribution and Excretion

    Absorption

    Bioavailability is 20% following oral administration.

    5.5 Metabolism/Metabolites

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

    5.6 Biological Half-Life

    13 hours for bambuterol and 21 hours for the primary active metabolite terbutaline.

    5.7 Mechanism of Action

    The 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.