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
CHEBI:143782
CAS Number
62658-63-3
UNII
KT304VZO57
DrugBank ID
DB08807
TTD ID
D0H5MB
INTEDE ID
DR0220

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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Potassium voltage-gated channel subfamily H member 2 (KCNH2) OTZX881H KCNH2_HUMAN Gene/Protein Processing [6]
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.
6 Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.