Bitolterol

Synopsis, Chemistry

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Also known as: 30392-41-7, Tornalate, Bitolterol mesilate, Bitolterol methanesulfonate, Bitolterol mesilat, Bitolterol (mesylate)

Molecular Formula

C₂₉H₃₅NO₈S

Molecular Weight

557.7 g/mol

InChI Key

HODFCFXCOMKRCG-UHFFFAOYSA-N

FDA UNII

4E53T3611U

Bitolterol Mesylate is the mesylate salt of bitolterol, a diester sympathomimetic amine with bronchodilator activity. As an ester prodrug, bitolterol is hydrolyzed by esterases to its active metabolite colterol (N-t-butylarterenol). Colterol selectively binds to and activates beta-2 adrenergic receptors in bronchiolar smooth muscle, thereby causing stimulation of adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cAMP). Increased intracellular cAMP levels cause relaxation of bronchial smooth muscle. This increases air flow and prevents bronchospasms and may eventually lead to an improvement of airway function.

1 2D Structure

Bitolterol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyl)oxyphenyl] 4-methylbenzoate;methanesulfonic acid

2.1.2 InChI

InChI=1S/C28H31NO5.CH4O3S/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21;1-5(2,3)4/h6-16,23,29-30H,17H2,1-5H3;1H3,(H,2,3,4)

2.1.3 InChI Key

HODFCFXCOMKRCG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC=C(C=C1)C(=O)OC2=C(C=C(C=C2)C(CNC(C)(C)C)O)OC(=O)C3=CC=C(C=C3)C.CS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

4E53T3611U

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bitolterol

2. Bitolterol Methanesulfonate

3. S-1540

4. Tornalate

5. Win 32784

2.3.2 Depositor-Supplied Synonyms

1. 30392-41-7

2. Tornalate

3. Bitolterol Mesilate

4. Bitolterol Methanesulfonate

5. Bitolterol Mesilat

6. Bitolterol (mesylate)

7. Bitolterol Mesylate [usan]

8. (tert-butyl)[beta-hydroxy-3,4-bis(p-toluoyloxy)phenethyl]ammonium Methanesulphonate

9. Win 32784

10. Win-32784

11. Win 32,784

12. 4-(2-(tert-butylamino)-1-hydroxyethyl)-o-phenylene Di-p-toluate Methanesulfonate (salt)

13. 4e53t3611u

14. Effectin

15. Bitolterol Mesilate (jan)

16. Bitolterol Mesylate (usan)

17. [4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyl)oxyphenyl] 4-methylbenzoate;methanesulfonic Acid

18. Benzoic Acid, 4-methyl-, 4-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-1,2-phenylene Ester Methanesulfonate (salt)

19. Bitolterol Mesilate [jan]

20. Biterol; Bitoterol Methanesulfonate; Effectin; Tornalate; Win 32784

21. Chebi:3134

22. (tert-butyl)(beta-hydroxy-3,4-bis(p-toluoyloxy)phenethyl)ammonium Methanesulphonate

23. Einecs 250-177-5

24. Asmalene

25. Produrol

26. Unii-4e53t3611u

27. Tornalate (tn)

28. 4-(2-(t-butylamino)-1-hydroxyethyl)-o-phenylene Di-p-toluate Mesilate

29. S-1540

30. Schembl4371

31. Alpha((tert-butylamino)methyl)-3,4-dihydroxybenzyl Alcohol 3,4-di-p-toluate Methanesulfonate (salt)

32. Chembl1200405

33. Dtxsid80952735

34. Bitolterol Mesylate [vandf]

35. Bitolterol Mesilate [mart.]

36. Bitolterol Mesilate [who-dd]

37. Bitolterol Methanesulfonate [mi]

38. Bitolterol Mesylate [orange Book]

39. P-toluic Acid, 4-(2-(tert-butylamino)-1-hydroxyethyl)-o-phenylene Ester, Methanesulfonate(salt)

40. D00684

41. Q27105949

42. .alpha.((tert-butylamino)methyl)-3,4-dihydroxybenzyl Alcohol 3,4-di-p-toluate Methanesulfonate (salt)

43. .alpha.((tert-butylamino)methyl)-3,4-dihydroxybenzyl Alcohol 3,4-di-p-toluate Methanesulphonate (salt)

44. 4-(2-(tert-butylamino)-1-hydroxyethyl)-1,2-phenylene Bis(4-methylbenzoate) Methanesulfonate (salt)

45. 4-(2-(tert-butylamino)-1-hydroxyethyl)-1,2-phenylene Bis(4-methylbenzoate) Methanesulphonate (salt)

46. 4-(2-(tert-butylamino)-1-hydroxyethyl)-o-phenylene Di-p-toluate Methanesulphonate (salt)

47. 4-methyl-benzoic Acid 1,1'-[4-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,2-phenylene] Ester Methanesulfonate

48. Alpha ((t-butylamino)methyl)-3,4-dihydroxybenzyl Alcohol 3,4-di(p-toluate) Methanesulfonate

49. Alpha ((t-butylamino)methyl)-3,4-dihydroxybenzyl Alcohol 3,4-di(p-toluate) Methanesulphonate

50. Benzoic Acid, 4-methyl-, 4-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-1,2-phenylene Ester Methanesulphonate (salt)

51. Benzoic Acid, 4-methyl-, 4-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-1,2-phenylene Ester, Methanesulfonate (1:1)

52. Benzoic Acid, 4-methyl-, 4-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-1,2-phenylene Ester, Methanesulphonate (1:1)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₅NO₈S
Molecular Weight	557.7 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	10
Exact Mass	557.20833825 g/mol
Monoisotopic Mass	557.20833825 g/mol
Topological Polar Surface Area	148 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	751
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	2