Details of the Drug

General Information of Drug (ID: DMIFYLX)

Drug Name
Bopindolol
Synonyms
BOPINDOLOL; 62658-63-3; Sandonorm; (+-)-Bopindolol; 1-(tert-Butylamino)-3-((2-methyl-1H-indol-4-yl)oxy)propan-2-yl benzoate; Bopindololum [INN-Latin]; Bopindolol [INN]; UUOJIACWOAYWEZ-UHFFFAOYSA-N; Bopindolol (INN); Wandonorm; 69010-88-4; NCGC00163155-01; Sandonorm (TN); (+-)-4-(2-Benzoyloxy-3-tert-butylaminopropoxy)-2-methylindole; DSSTox_CID_2684; DSSTox_RID_76690; (+-)-1-(tert-Butylamino)-3-((2-methylindol-4-yl)oxy)-2-propanol benzoate (ester); DSSTox_GSID_22684
Indication
Disease Entry ICD 11 Status REF
Hypertension BA00-BA04 Approved [1]
Affected Organisms
Humans and other mammals
ATC Code
C07AA17: Bopindolol
C07AA: Beta blocking agents, non-selective
C07A: BETA BLOCKING AGENTS
C07: BETA BLOCKING AGENTS
C: CARDIOVASCULAR SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 380.5
Logarithm of the Partition Coefficient (xlogp) 4.7
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Elimination
0% of drug is excreted from urine in the unchanged form [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.05069 micromolar/kg/day [3]
Water Solubility
The ability of drug to dissolve in water is measured as 3.3 mg/mL [2]
Chemical Identifiers
Formula
C23H28N2O3
IUPAC Name
[1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl] benzoate
Canonical SMILES
CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3
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
InChIKey
UUOJIACWOAYWEZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
44112
ChEBI ID
CHEMBL357995
CAS Number
62658-63-3
UNII
KT304VZO57
DrugBank ID
DB08807
TTD ID
D0H5MB
INTEDE ID
DR0220
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Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor beta-3 (ADRB3) TTMXGCW ADRB3_HUMAN Modulator [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Hypertension
ICD Disease Classification BA00-BA04
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Adrenergic receptor beta-3 (ADRB3) DTT ADRB3 7.81E-01 0.02 0.16
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 5.64E-01 2.36E-02 1.75E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS applied to over 900 drugs
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Effect of propranolol, alprenolol, pindolol, and bopindolol on beta 2-adrenoceptor density in human lymphocytes. J Cardiovasc Pharmacol. 1986;8 Suppl 6:S70-3.
5 Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432.