Levobunolol (CHEM022260)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:25:58 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022260
Identification
Common NameLevobunolol
ClassSmall Molecule
DescriptionA nonselective beta-adrenoceptor antagonist used in the treatment of glaucoma.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-BunololChEBI
(S)-5-(3-((1,1-Dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenoneChEBI
LevobunololumChEBI
Akorn brand OF levobunolol hydrochlorideHMDB
Allergan brand OF levobunolol hydrochlorideHMDB
Apotex brand OF levobunolol hydrochlorideHMDB
Levobunolol hydrochlorideHMDB
Novo-levobunololHMDB
UltracortenolHMDB
VistaganHMDB
Ratio levobunololHMDB
Apo-levobunololHMDB
PMS LevobunololHMDB
PMSLevobunololHMDB
Pharm allergan brand OF levobunolol hydrochlorideHMDB
Pharmascience brand OF levobunolol hydrochlorideHMDB
AKBetaHMDB
Novopharm brand OF levobunolol hydrochlorideHMDB
Pharm-allergan brand OF levobunolol hydrochlorideHMDB
Ratiopharm brand OF levobunolol hydrochlorideHMDB
Ratio-levobunololHMDB
Apo levobunololHMDB
ApoLevobunololHMDB
BetaganHMDB
Ciba vision brand OF levobunolol hydrochlorideHMDB
Novo levobunololHMDB
NovoLevobunololHMDB
PMS-LevobunololHMDB
Chemical FormulaC17H25NO3
Average Molecular Mass291.385 g/mol
Monoisotopic Mass291.183 g/mol
CAS Registry Number47141-42-4
IUPAC Name5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one
Traditional Nameakβ
SMILESCC(C)(C)NC[C@H](O)COC1=CC=CC2=C1CCCC2=O
InChI IdentifierInChI=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
InChI KeyIXHBTMCLRNMKHZ-LBPRGKRZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassNot Available
Direct ParentTetralins
Alternative Parents
Substituents
  • Tetralin
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • 1,2-aminoalcohol
  • Ketone
  • Secondary alcohol
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.06ALOGPS
logP2.18ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.28 m³·mol⁻¹ChemAxon
Polarizability33.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08gi-9540000000-243680d4a0d98a06ee5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-08mu-9423000000-24d9e3e549ee0f3caefcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1290000000-a27d598a50efb04fd09eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9470000000-fade873eb3e9b9280e3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9400000000-9c86007a0342c84063d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-1690000000-01bd12a64aa5a1ac1b0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f14eecc41eae40c5ae10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-bd973c4edbfdfc4ff33cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-528baf592ca874e0be73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022l-3490000000-47baa556e9ab27cc0b6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9400000000-0bc68579194e5bf27651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-23bba37d597734cfc791Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-1910000000-29bcb195f7a66d163c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-0900000000-698fee7bcd270c336dabSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01210
HMDB IDHMDB0015341
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLevobunolol
Chemspider ID36089
ChEBI ID6438
PubChem Compound ID39468
Kegg Compound IDC07914
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63.
2. Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61.
3. Novack GD: Levobunolol for the long-term treatment of glaucoma. Gen Pharmacol. 1986;17(4):373-7.
4. Leung M, Grunwald JE: Short-term effects of topical levobunolol on the human retinal circulation. Eye (Lond). 1997;11 ( Pt 3):371-6.
5. Ogasawara H, Yoshida A, Fujio N, Konno S, Ishiko S: [Effect of topical levobunolol on retinal, optic nerve head, and choroidal circulation in normal volunteers]. Nippon Ganka Gakkai Zasshi. 1999 Jul;103(7):544-50.
6. Ishibashi T, Yokoi N, Kinoshita S: Comparison of the effects of topical levobunolol and timolol solution on the human ocular surface. Cornea. 2003 Nov;22(8):709-15.
7. Dong Y, Ishikawa H, Wu Y, Yoshitomi T: Vasodilatory mechanism of levobunolol on vascular smooth muscle cells. Exp Eye Res. 2007 Jun;84(6):1039-46. Epub 2007 Jan 27.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19626454
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20960417
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21368570
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23390358
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2873545
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2881799
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=3019819
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=3050679
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=3058836
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=3062528
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=3067745
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=3513594
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=3881032
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=3912600