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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:05 UTC
HMDB IDHMDB0015696
Secondary Accession Numbers
  • HMDB15696
Metabolite Identification
Common NameBopindolol
DescriptionBopindolol is only found in individuals that have used or taken this drug. It is a beta blocker. It is an ester which acts as a prodrug for 'pindolol':http://drugbank.ca/drugs/DB00960. 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.
Structure
Data?1582753324
Synonyms
ValueSource
SandonormKegg
1-(Tert-butylamino)-3-((2-methylindo)-4-yl)-2-propanol benzoateHMDB
Bopindolol, (+-)-isomerHMDB
Chemical FormulaC23H28N2O3
Average Molecular Weight380.48
Monoisotopic Molecular Weight380.209992772
IUPAC Name1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate
Traditional Namebopindolol
CAS Registry Number69010-88-4
SMILES
CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1
InChI Identifier
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
InChI KeyUUOJIACWOAYWEZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Indole
  • Indole or derivatives
  • Benzoyl
  • Alkyl aryl ether
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point152 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP4.45ALOGPS
logP4.67ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)16.8ChemAxon
pKa (Strongest Basic)9.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.35 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.07 m³·mol⁻¹ChemAxon
Polarizability43.08 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.25931661259
DarkChem[M-H]-189.50231661259
DeepCCS[M+H]+191.96630932474
DeepCCS[M-H]-189.57930932474
DeepCCS[M-2H]-223.90530932474
DeepCCS[M+Na]+199.24130932474
AllCCS[M+H]+194.732859911
AllCCS[M+H-H2O]+191.932859911
AllCCS[M+NH4]+197.232859911
AllCCS[M+Na]+197.932859911
AllCCS[M-H]-198.332859911
AllCCS[M+Na-2H]-198.232859911
AllCCS[M+HCOO]-198.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BopindololCC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C14268.9Standard polar33892256
BopindololCC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C12998.6Standard non polar33892256
BopindololCC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C12978.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bopindolol,1TMS,isomer #1CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C3012.7Semi standard non polar33892256
Bopindolol,1TMS,isomer #1CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C2894.0Standard non polar33892256
Bopindolol,1TMS,isomer #1CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C3646.1Standard polar33892256
Bopindolol,1TMS,isomer #2CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]13176.2Semi standard non polar33892256
Bopindolol,1TMS,isomer #2CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]13118.4Standard non polar33892256
Bopindolol,1TMS,isomer #2CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]13828.2Standard polar33892256
Bopindolol,2TMS,isomer #1CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C3192.6Semi standard non polar33892256
Bopindolol,2TMS,isomer #1CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C3051.6Standard non polar33892256
Bopindolol,2TMS,isomer #1CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C3547.9Standard polar33892256
Bopindolol,1TBDMS,isomer #1CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C3190.3Semi standard non polar33892256
Bopindolol,1TBDMS,isomer #1CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C3120.4Standard non polar33892256
Bopindolol,1TBDMS,isomer #1CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C3690.0Standard polar33892256
Bopindolol,1TBDMS,isomer #2CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]13432.3Semi standard non polar33892256
Bopindolol,1TBDMS,isomer #2CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]13294.8Standard non polar33892256
Bopindolol,1TBDMS,isomer #2CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]13839.6Standard polar33892256
Bopindolol,2TBDMS,isomer #1CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C3605.8Semi standard non polar33892256
Bopindolol,2TBDMS,isomer #1CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C3432.5Standard non polar33892256
Bopindolol,2TBDMS,isomer #1CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C3641.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bopindolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7911000000-408594fb00778767ea812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bopindolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 10V, Positive-QTOFsplash10-053r-0659000000-0b5a95ba7db5f64b371e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 20V, Positive-QTOFsplash10-0a59-3943000000-057c41afa69ae73f20ef2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 40V, Positive-QTOFsplash10-0a59-3900000000-dfe073c414f0adca5ffe2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 10V, Negative-QTOFsplash10-00ba-2926000000-db6f18d6a7284c3cb7542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 20V, Negative-QTOFsplash10-0002-1900000000-058c780f09bbe5de86122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 40V, Negative-QTOFsplash10-000t-1900000000-e499cd0c6a8423dc66a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 10V, Positive-QTOFsplash10-001i-0239000000-262fbf226d3c984088f52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 20V, Positive-QTOFsplash10-0zi0-2894000000-cdb9d72cc2695ceff72c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 40V, Positive-QTOFsplash10-0a4i-5900000000-b1d6ff0f3bc22ddb8af92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 10V, Negative-QTOFsplash10-004i-0319000000-3a4a7e375a97ecf4e5ab2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 20V, Negative-QTOFsplash10-03mi-1920000000-d0f867cab949edc4db682021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bopindolol 40V, Negative-QTOFsplash10-004i-9700000000-d0de49d04fe8b4c83f4c2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08807 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08807 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08807
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID40146
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBopindolol
METLIN IDNot Available
PubChem Compound44112
PDB IDNot Available
ChEBI ID143782
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Joseph SS, Lynham JA, Molenaar P, Grace AA, Colledge WH, Kaumann AJ: Intrinsic sympathomimetic activity of (-)-pindolol mediated through a (-)-propranolol-resistant site of the beta1-adrenoceptor in human atrium and recombinant receptors. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):496-503. Epub 2003 Nov 8. [PubMed:14608456 ]
  3. Doggrell SA: Effects of (+/-)- (+)- and (-)-metoprolol, (+/-)- (+)- and (-)-pindolol, (+/-)-mepindolol and (+/-)-bopindolol on the rat left atria and portal vein. Gen Pharmacol. 1991;22(6):1169-77. [PubMed:1687398 ]
  4. Berendsen HH, Broekkamp CL, Van Delft AM: Antagonism of 8-OH-DPAT-induced behaviour in rats. Eur J Pharmacol. 1990 Oct 2;187(1):97-103. [PubMed:2148726 ]
  5. Watkins DJ, Lawrence AJ, Lewis SJ, Jarrott B: Loss of [125I]-pindolol binding to beta-adrenoceptors on rat nodose ganglion after chronic isoprenaline treatment. J Auton Nerv Syst. 1996 Aug 27;60(1-2):12-6. [PubMed:8884690 ]
  6. Brodde OE, Michel MC, Wang XL, Zerkowski HR: Chronic beta-adrenoceptor antagonist treatment modulates human cardiac and vascular beta-adrenoceptor density in a subtype-selective fashion. J Hypertens Suppl. 1988 Dec;6(4):S497-500. [PubMed:2907348 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Rubenstein LA, Zauhar RJ, Lanzara RG: Molecular dynamics of a biophysical model for beta2-adrenergic and G protein-coupled receptor activation. J Mol Graph Model. 2006 Dec;25(4):396-409. Epub 2006 Mar 30. [PubMed:16574446 ]
  2. Dejgaard A, Liggett SB, Christensen NJ, Cryer PE, Hilsted J: Adrenergic receptors are a fallible index of adrenergic denervation hypersensitivity. Scand J Clin Lab Invest. 1991 Dec;51(8):659-66. [PubMed:1666931 ]
  3. Wheeldon NM, Newnham DM, Fraser GC, McDevitt DG, Lipworth BJ: The effect of pindolol on creatine kinase is not due to beta 2-adrenoceptor partial agonist activity. Br J Clin Pharmacol. 1991 Jun;31(6):723-4. [PubMed:1678274 ]
  4. Doggrell SA: Effects of (+/-)- (+)- and (-)-metoprolol, (+/-)- (+)- and (-)-pindolol, (+/-)-mepindolol and (+/-)-bopindolol on the rat left atria and portal vein. Gen Pharmacol. 1991;22(6):1169-77. [PubMed:1687398 ]
  5. Doggrell SA: Relaxant and beta 2-adrenoceptor blocking activities of (+/- )-, (+)- and (-)-pindolol on the rat isolated aorta. J Pharm Pharmacol. 1990 Jun;42(6):444-6. [PubMed:1979630 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
References
  1. Dawson LA, Nguyen HQ: The role of 5-HT(1A) and 5-HT(1B/1D) receptors on the modulation of acute fluoxetine-induced changes in extracellular 5-HT: the mechanism of action of (+/-)pindolol. Neuropharmacology. 2000 Apr 3;39(6):1044-52. [PubMed:10727715 ]
  2. Ariani K, Hamblin MW, Tan GL, Stratford CA, Ciaranello RD: G protein dependent alterations in [125I]iodocyanopindolol and +/- cyanopindolol binding at 5-HT1B binding sites in rat brain membranes. Neurochem Res. 1989 Sep;14(9):835-43. [PubMed:2512511 ]
  3. Leonhardt S, Herrick-Davis K, Titeler M: Detection of a novel serotonin receptor subtype (5-HT1E) in human brain: interaction with a GTP-binding protein. J Neurochem. 1989 Aug;53(2):465-71. [PubMed:2664084 ]
  4. Herrick-Davis K, Titeler M, Leonhardt S, Struble R, Price D: Serotonin 5-HT1D receptors in human prefrontal cortex and caudate: interaction with a GTP binding protein. J Neurochem. 1988 Dec;51(6):1906-12. [PubMed:3141589 ]
  5. Terron JA, Lopez-Munoz FJ, Hong E, Villalon CM: 2-(2-Aminoethyl)-quinoline (D-1997): a novel agonist at 5-hydroxytryptamine1-like receptors in the canine basilar artery. Arch Int Pharmacodyn Ther. 1994 Jan-Feb;327(1):56-68. [PubMed:7944828 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. Smeraldi E, Benedetti F, Barbini B, Campori E, Colombo C: Sustained antidepressant effect of sleep deprivation combined with pindolol in bipolar depression. A placebo-controlled trial. Neuropsychopharmacology. 1999 Apr;20(4):380-5. [PubMed:10088139 ]
  2. Haddjeri N, de Montigny C, Blier P: Modulation of the firing activity of rat serotonin and noradrenaline neurons by (+/-)pindolol. Biol Psychiatry. 1999 May 1;45(9):1163-9. [PubMed:10331108 ]
  3. Gobert A, Millan MJ: Modulation of dialysate levels of dopamine, noradrenaline, and serotonin (5-HT) in the frontal cortex of freely-moving rats by (-)-pindolol alone and in association with 5-HT reuptake inhibitors: comparative roles of beta-adrenergic, 5-HT1A, and 5-HT1B receptors. Neuropsychopharmacology. 1999 Aug;21(2):268-84. [PubMed:10432475 ]
  4. Andree B, Thorberg SO, Halldin C, Farde L: Pindolol binding to 5-HT1A receptors in the human brain confirmed with positron emission tomography. Psychopharmacology (Berl). 1999 Jun;144(3):303-5. [PubMed:10435400 ]
  5. Fornal CA, Martin FJ, Metzler CW, Jacobs BL: Pindolol suppresses serotonergic neuronal activity and does not block the inhibition of serotonergic neurons produced by 8-hydroxy-2-(di-n-propylamino)tetralin in awake cats. J Pharmacol Exp Ther. 1999 Oct;291(1):229-38. [PubMed:10490909 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular weight:
43518.6
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]