Details of the Drug

General Information of Drug (ID: DMTNFCQ)

Drug Name

Levobunolol

Synonyms

Akbeta; Betagan; Levobunololum; Levobunolol HCl; Betegan (TN); Levobunolol (INN); Levobunolol [INN:BAN]; Levobunololum [INN-Latin]; Liquifilm (TN); W-6412A; W-7000A; AK-Beta (TN); (-)-Bunolol; (S)-5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenone; 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one; 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydronaphthalen-1(2H)-one

Indication

Disease Entry	ICD 11	Status	REF
Ocular hypertension	9C61.01	Approved	[1]
Open-angle glaucoma	9C61	Approved	[2]
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Therapeutic Class

Sympatholytics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

291.4

Logarithm of the Partition Coefficient (xlogp)

2.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The absorption of drug is 80% []
Bioavailability: 75% of drug becomes completely available to its intended biological destination(s) [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 20 hours [4]
Metabolism: The drug is metabolized via the hepatic []

Chemical Identifiers

Formula: C17H25NO3
IUPAC Name: 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one
Canonical SMILES: CC(C)(C)NC[C@@H](COC1=CC=CC2=C1CCCC2=O)O
InChI: InChI=1S/C17H25NO3/c1-17(2,3)18-10-12(19)11-21-16-9-5-6-13-14(16)7-4-8-15(13)20/h5-6,9,12,18-19H,4,7-8,10-11H2,1-3H3/t12-/m0/s1
InChIKey: IXHBTMCLRNMKHZ-LBPRGKRZSA-N

Cross-matching ID

PubChem CID: 39468
ChEBI ID: CHEBI:6438
CAS Number: 47141-42-4
DrugBank ID: DB01210
TTD ID: D00IUG
INTEDE ID: DR0933

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-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Levobunolol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Bepridil	DM0RKS4	Moderate	Increased risk of cardiac depression by the combination of Levobunolol and Bepridil.	Angina pectoris [BA40]	[7]
Dronedarone	DMA8FS5	Moderate	Increased risk of bradycardia by the combination of Levobunolol and Dronedarone.	Angina pectoris [BA40]	[8]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Levobunolol and Atracurium.	Corneal disease [9A76-9A78]	[9]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Levobunolol and Mivacurium.	Corneal disease [9A76-9A78]	[9]
Pancuronium	DMB0VY8	Moderate	Additive cardiorespiratory depression effects by the combination of Levobunolol and Pancuronium.	Corneal disease [9A76-9A78]	[9]
Pasireotide	DMHM7JS	Moderate	Increased risk of atrioventricular block by the combination of Levobunolol and Pasireotide.	Cushing syndrome [5A70]	[10]
Levamlodipine	DM92S6N	Moderate	Increased risk of cardiac depression by the combination of Levobunolol and Levamlodipine.	Hypertension [BA00-BA04]	[7]
Clevidipine butyrate	DMW4M97	Moderate	Increased risk of cardiac depression by the combination of Levobunolol and Clevidipine butyrate.	Hypertension [BA00-BA04]	[7]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Decreased metabolism of Levobunolol caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[11]
Siponimod	DM2R86O	Major	Increased risk of atrioventricular block by the combination of Levobunolol and Siponimod.	Multiple sclerosis [8A40]	[12]
Fingolimod	DM5JVAN	Moderate	Increased risk of bradycardia by the combination of Levobunolol and Fingolimod.	Multiple sclerosis [8A40]	[13]
Ozanimod	DMT6AM2	Moderate	Increased risk of bradycardia by the combination of Levobunolol and Ozanimod.	Multiple sclerosis [8A40]	[14]
Polythiazide	DMCH80F	Moderate	Increased risk of hyperglycemia by the combination of Levobunolol and Polythiazide.	Oedema [MG29]	[15]
Silodosin	DMJSBT6	Moderate	Additive hypotensive effects by the combination of Levobunolol and Silodosin.	Prostate hyperplasia [GA90]	[16]
Pipecuronium	DM5F84A	Moderate	Additive neuromuscular blocking effects by the combination of Levobunolol and Pipecuronium.	Tonus and reflex abnormality [MB47]	[9]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Levobunolol and Vecuronium.	Tonus and reflex abnormality [MB47]	[9]
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⏷ Show the Full List of 16 DDI Information of This Drug

References

1	Levobunolol FDA Label
2	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: 570).
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Binding of beta-adrenoceptor antagonists to rat and rabbit lung: special reference to levobunolol. Arzneimittelforschung. 1984;34(5):579-84.
6	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.
7	Henry M, Kay MM, Viccellio P "Cardiogenic shock associated with calcium-channel and beta blockers: reversal with intravenous calcium chloride." Am J Emerg Med 3 (1985): 334-6. [PMID: 2860911]
8	Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
9	Harrah MD, Way WL, Katzung BG "The interaction of d-tubocurarine with antiarrhythmic drugs." Anesthesiology 33 (1970): 406-10. [PMID: 5512329]
10	Canadian Pharmacists Association.
11	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
12	Cerner Multum, Inc. "Australian Product Information.".
13	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
14	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
15	Dean S, Kendall MJ, Potter S, Thompson MH, Jackson DA "Nadolol in combination with indapamide and xipamide in resistant hypertensives." Eur J Clin Pharmacol 28 (1985): 29-33. [PMID: 3987783]
16	Chrysant SG "Experience with terazosin administered in combination with other antihypertensive agents." Am J Med 80 (1986): 55-61. [PMID: 2872808]