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Bopindolol

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Also known as: 62658-63-3, Rac bopindolol, Bopindolol [inn], Sandonorm, 1-(tert-butylamino)-3-((2-methyl-1h-indol-4-yl)oxy)propan-2-yl benzoate, (+/-)-bopindolol

Molecular Formula

C₂₃H₂₈N₂O₃

Molecular Weight

380.5 g/mol

InChI Key

UUOJIACWOAYWEZ-UHFFFAOYSA-N

FDA UNII

KT304VZO57

Bopindolol (INN) is an ester prodrug for the beta blocker [pindolol].

1 2D Structure

Bopindolol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl] benzoate

2.1.2 InChI

InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3

2.1.3 InChI Key

UUOJIACWOAYWEZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

KT304VZO57

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(tert-butylamino)-3-((2-methylindo)-4-yl)-2-propanol Benzoate

2. Bopindolol, (+-)-isomer

3. Lt 31-200

2.3.2 Depositor-Supplied Synonyms

1. 62658-63-3

2. Rac Bopindolol

3. Bopindolol [inn]

4. Sandonorm

5. 1-(tert-butylamino)-3-((2-methyl-1h-indol-4-yl)oxy)propan-2-yl Benzoate

6. (+/-)-bopindolol

7. [1-(tert-butylamino)-3-[(2-methyl-1h-indol-4-yl)oxy]propan-2-yl] Benzoate

8. Kt304vzo57

9. Bopindolol (inn)

10. 2-propanol, 1-[(1,1-dimethylethyl)amino]-3-[(2-methyl-1h-indol-4-yl)oxy]-, Benzoate (ester)

11. Ncgc00163155-01

12. Sandonorm (tn)

13. Dsstox_cid_2684

14. 1-(tert-butylamino)-3-[(2-methyl-1h-indol-4-yl)oxy]propan-2-yl Benzoate

15. Dsstox_rid_76690

16. Dsstox_gsid_22684

17. (+-)-bopindolol

18. Bopindololum

19. Bopindololum [inn-latin]

20. Cas-62658-63-3

21. Unii-kt304vzo57

22. Rac Bopindolol-[d9]

23. Bopindolol [mi]

24. (+-)-4-(2-benzoyloxy-3-tert-butylaminopropoxy)-2-methylindole

25. (+-)-1-(tert-butylamino)-3-((2-methylindol-4-yl)oxy)-2-propanol Benzoate (ester)

26. Bopindolol [who-dd]

27. Schembl49500

28. (+-)-1-((1,1-dimethylethyl)amino)-3-((2-methyl-1h-indol-4-yl)oxy)-2-propanol Benzoate (ester)

29. 2-propanol, 1-((1,1-dimethylethyl)amino)-3-((2-methyl-1h-indol-4-yl)oxy)-, Benzoate (ester), (+-)-

30. 69010-88-4

31. Mls003882860

32. Bopindolol, Bopindolol Maleate

33. Chembl357995

34. Dtxsid6022684

35. Chebi:143782

36. Hms2089o20

37. Hy-b1562

38. Tox21 112017

39. Tox21_112017

40. Akos016014321

41. Tox21_112017_1

42. Db08807

43. Ncgc00163155-02

44. Ncgc00263654-01

45. Lt-31200

46. Smr001550598

47. Cs-0013446

48. Ft-0663594

49. D07537

50. Ab01275452-01

51. A922919

52. L013383

53. Q834660

54. Sr-05000001453

55. Sr-05000001453-1

56. 4-(2-benzoyloxy-3-t-butylamino-propoxy) -2-methyl Indole

57. 4-(2-benzoyloxy-3-tert.butylaminopropoxy)-2-methyl-indole

58. 1-(tert-butylamino)-3-(2-methyl-1h-indol-4-yloxy)propan-2-yl Benzoate

59. 2-(tert-butylamino)-1-{[(2-methyl-1h-indol-4-yl)oxy]methyl}ethyl Benzoate

60. (+/-)-1-(tert-butylamino)-3-((2-methylindol-4-yl)oxy)-2-propanol Benzoate (ester)

61. 2-[(1,1-dimethylethyl)amino]-1-{[(2-methyl-1h-indol-4-yl)oxy]methyl}ethyl Benzoate

62. 1-((1,1-dimethylethyl)amino)-3-((2-methyl-1h-indol-4-yl)oxy)-2-propanol Benzoate Ester

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₈N₂O₃
Molecular Weight	380.5 g/mol
XLogP3	4.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	9
Exact Mass	380.20999276 g/mol
Monoisotopic Mass	380.20999276 g/mol
Topological Polar Surface Area	63.4 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	499
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 management of hypertension, edema, ventricular tachycardias, and atrial fibrillation.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bopindolol is a prodrug of pindolol. Pindolol is a non-selective beta-adrenergic antagonist (beta-blocker) which possesses intrinsic sympathomimetic activity (ISA) in therapeutic dosage ranges but does not possess quinidine-like membrane stabilizing activity. Pindolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Pindolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Pindolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, pindolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.

5.2 MeSH Pharmacological Classification

Adrenergic beta-Antagonists

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety. (See all compounds classified as Adrenergic beta-Antagonists.)

5.3 ATC Code

C - Cardiovascular system

C07 - Beta blocking agents

C07A - Beta blocking agents

C07AA - Beta blocking agents, non-selective

C07AA17 - Bopindolol

5.4 Mechanism of Action

Bopindolol (as pindolol) non-selectively blocks beta-1 adrenergic receptors mainly in the heart, inhibiting the effects of epinephrine and norepinephrine resulting in a decrease in heart rate and blood pressure. By binding beta-2 receptors in the juxtaglomerular apparatus, Pindolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production and therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.

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