Details of the Drug

General Information of Drug (ID: DMYJ8Z3)

Drug Name

Alprenolol

Synonyms

Alfeprol; Alpheprol; Alprenololum; Yobir; Alfeprol [Russian]; Alprenolol (INN); Alprenolol [INN:BAN]; Alprenololum [INN-Latin]; Apllobal (TN); Aptine (TN); Aptol (TN); Duriles (TN); Gubernal (TN); Regletin (TN); Yobir (TN); H-56-28; 1-(2-Allylphenoxy)-3-isopropylamino-2-propanol; 1-(o-Allylphenoxy)-3-(isopropylamino)-2-propanol; 1-(o-Allylphenoxy)-3-isopropylamino)-2-propanol; 1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol; 1-[2-(propen-2-ylphenoxy)]-3-(isopropylamino)propan-2-ol

Indication

Disease Entry	ICD 11	Status	REF
Hypertension	BA00-BA04	Withdrawn from market	[1]
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Therapeutic Class

Antiarrhythmic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

249.35

Logarithm of the Partition Coefficient (xlogp)

3.1

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]
Clearance: The drug present in the plasma can be removed from the body at the rate of 15 mL/min/kg [3]
Elimination: 0.5% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 2 - 3 hours [3]
Metabolism: The drug is metabolized via the hepatic []
Unbound Fraction: The unbound fraction of drug in plasma is 0.18% [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 3.2 L/kg [3]
Water Solubility: The ability of drug to dissolve in water is measured as 50 mg/mL [2]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Adverse drug reaction	Not Available	CYP2D6	OTZJC802	[4]
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Chemical Identifiers

Formula: C15H23NO2
IUPAC Name: 1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol
Canonical SMILES: CC(C)NCC(COC1=CC=CC=C1CC=C)O
InChI: InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3
InChIKey: PAZJSJFMUHDSTF-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2119
ChEBI ID: CHEBI:51211
CAS Number: 13655-52-2
DrugBank ID: DB00866
TTD ID: D01VAB
VARIDT ID: DR00811
INTEDE ID: DR0076

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	Antagonist	[5]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[6]

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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	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Drug Response	[4]
Epidermal growth factor receptor (EGFR)	OTAPLO1S	EGFR_HUMAN	Post-Translational Modifications	[5]
Renin (REN)	OT52GZR2	RENI_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 563).
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
5	Beta-blockers alprenolol and carvedilol stimulate beta-arrestin-mediated EGFR transactivation. Proc Natl Acad Sci U S A. 2008 Sep 23;105(38):14555-60.
6	A novel screening strategy to identify ABCB1 substrates and inhibitors. Naunyn Schmiedebergs Arch Pharmacol. 2009 Jan;379(1):11-26.
7	Influence of the CYP2D6 isoenzyme in patients treated with venlafaxine for major depressive disorder: clinical and economic consequences. PLoS One. 2014 Nov 4;9(11):e90453.
8	Plasma renin concentration in essential hypertension during beta-adrenergic blockade and vasodilator therapy. Eur J Clin Pharmacol. 1977 Oct 14;12(2):93-6. doi: 10.1007/BF00645128.