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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[5]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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.