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Bambuterol Hydrochloride

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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

Bambuterol Hydrochloride

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 Formula	C₁₈H₂₉N₃O₅
Molecular Weight	367.4 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Exact Mass	367.21072103 g/mol
Monoisotopic Mass	367.21072103 g/mol
Topological Polar Surface Area	91.3 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	446
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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