Details of the Drug

General Information of Drug (ID: DMV52CP)

Drug Name

BUCINDOLOL

Synonyms

Bucindolol; 71119-11-4; Bucindolol [INN:BAN]; Bucindololum [INN-Latin]; CHEMBL321582; C22H25N3O2; NCGC00167817-01; 2-(2-Hydroxy-3-((2-(1H-indol-3-yl)-1,1-dimethylethyl)amino)propoxy)benzonitrile; DSSTox_RID_81872; DSSTox_CID_26744; DSSTox_GSID_46744; Bucindololum; 2-[2-Hydroxy-3-[2-(indol-3-yl)-1,1-dimethylethylamino]propoxy]benzonitrile; Benzonitrile, 2-(2-hydroxy-3-((2-(1H-indol-3-yl)-1,1-dimethylethyl)amino)propoxy)-; 2-[2-Hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy]benzonitrile

Indication

Disease Entry	ICD 11	Status	REF
Atrial fibrillation	BC81.3	Phase 2/3	[1]
Hypertension	BA00-BA04	Phase 2	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

363.5

Logarithm of the Partition Coefficient (xlogp)

3.3

Rotatable Bond Count (rotbonds)

8

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

4

Chemical Identifiers

Formula: C22H25N3O2
IUPAC Name: 2-[2-hydroxy-3-[[1-(1H-indol-3-yl)-2-methylpropan-2-yl]amino]propoxy]benzonitrile
Canonical SMILES: CC(C)(CC1=CNC2=CC=CC=C21)NCC(COC3=CC=CC=C3C#N)O
InChI: InChI=1S/C22H25N3O2/c1-22(2,11-17-13-24-20-9-5-4-8-19(17)20)25-14-18(26)15-27-21-10-6-3-7-16(21)12-23/h3-10,13,18,24-26H,11,14-15H2,1-2H3
InChIKey: FBMYKMYQHCBIGU-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 51045
CAS Number: 71119-11-4
DrugBank ID: DB12752
TTD ID: D03MZJ
VARIDT ID: DR00930
INTEDE ID: DR0238

Repurposed Drugs (RPD)

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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-1 (ADRB1)	TTR6W5O	ADRB1_HUMAN	Modulator	[3]
Adrenergic receptor beta-2 (ADRB2)	TT2CJVK	ADRB2_HUMAN	Modulator	[3]

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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	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Atrial fibrillation

ICD Disease Classification

BC81.3

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Adrenergic receptor beta-2 (ADRB2)	DTT	ADRB2	4.88E-01	-0.05	-0.12
Adrenergic receptor beta-2 (ADRB2)	DTT	ADRB2	7.10E-01	0.06	0.09
Cytochrome P450 2D6 (CYP2D6)	DME	CYP2D6	8.01E-02	6.73E-02	3.36E-01
Cytochrome P450 2D6 (CYP2D6)	DME	CYP2D6	2.91E-04	1.41E-01	6.14E-01

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2	ClinicalTrials.gov (NCT01970501) Genetically Targeted Therapy for the Prevention of Symptomatic Atrial Fibrillation in Patients With Heart Failure. U.S. National Institutes of Health.
3	Bucindolol has serotonin and alpha-adrenoceptor blocking properties. J Cardiovasc Pharmacol. 1985;7 Suppl 7:S67-9.
4	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.