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    Bopindolol

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    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

    2D Structure

    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 Weight 380.5 g/mol
    Molecular Formula C23H28N2O3
    XLogP34.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count9
    Exact Mass380.20999276 g/mol
    Monoisotopic Mass380.20999276 g/mol
    Topological Polar Surface Area63.4 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity499
    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 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.