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]
Therapeutic Class
Sympatholytics
Affected Organisms
Humans and other mammals
ATC Code
S01ED03: Levobunolol
S01ED: Beta blocking agents
S01E: ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
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) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
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
CHEMBL1201237
CAS Number
47141-42-4
UNII
G6317AOI7K
DrugBank ID
DB01210
TTD ID
D00IUG
INTEDE ID
DR0933
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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 Antagonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) 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]
⏷ 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]