Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:57 UTC |
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HMDB ID | HMDB0015341 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Levobunolol |
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Description | Levobunolol is only found in individuals that have used or taken this drug. It is a nonselective beta-adrenoceptor antagonist used in the treatment of glaucoma. [PubChem]Levobunolol's mechanism of action in reducing IOP is not clearly defined, but is believed to be due to a reduction of the production of aqueous humor via blockage of endogenous catecholamine-stimulated increases in cyclic adenosine monophosphate (AMP) concentrations within the ciliary processes. |
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Structure | CC(C)(C)NC[C@H](O)COC1=CC=CC2=C1CCCC2=O 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 |
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Synonyms | Value | Source |
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(-)-Bunolol | ChEBI | (S)-5-(3-((1,1-Dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenone | ChEBI | Levobunololum | ChEBI | Akorn brand OF levobunolol hydrochloride | HMDB | Allergan brand OF levobunolol hydrochloride | HMDB | Apotex brand OF levobunolol hydrochloride | HMDB | Levobunolol hydrochloride | HMDB | Novo-levobunolol | HMDB | Ultracortenol | HMDB | Vistagan | HMDB | Ratio levobunolol | HMDB | Apo-levobunolol | HMDB | PMS Levobunolol | HMDB | PMSLevobunolol | HMDB | Pharm allergan brand OF levobunolol hydrochloride | HMDB | Pharmascience brand OF levobunolol hydrochloride | HMDB | AKBeta | HMDB | Novopharm brand OF levobunolol hydrochloride | HMDB | Pharm-allergan brand OF levobunolol hydrochloride | HMDB | Ratiopharm brand OF levobunolol hydrochloride | HMDB | Ratio-levobunolol | HMDB | Apo levobunolol | HMDB | ApoLevobunolol | HMDB | Betagan | HMDB | Ciba vision brand OF levobunolol hydrochloride | HMDB | Novo levobunolol | HMDB | NovoLevobunolol | HMDB | PMS-Levobunolol | HMDB |
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Chemical Formula | C17H25NO3 |
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Average Molecular Weight | 291.3853 |
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Monoisotopic Molecular Weight | 291.183443671 |
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IUPAC Name | 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one |
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Traditional Name | akβ |
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CAS Registry Number | 47141-42-4 |
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SMILES | CC(C)(C)NC[C@H](O)COC1=CC=CC2=C1CCCC2=O |
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InChI Identifier | 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 |
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InChI Key | IXHBTMCLRNMKHZ-LBPRGKRZSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Tetralins |
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Sub Class | Not Available |
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Direct Parent | Tetralins |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 209 - 211 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.25 g/L | Not Available | LogP | 2.1 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Levobunolol,1TMS,isomer #1 | CC(C)(C)NC[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C | 2336.5 | Semi standard non polar | 33892256 | Levobunolol,1TMS,isomer #2 | CC(C)(C)N(C[C@H](O)COC1=CC=CC2=C1CCCC2=O)[Si](C)(C)C | 2513.2 | Semi standard non polar | 33892256 | Levobunolol,2TMS,isomer #1 | CC(C)(C)N(C[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C)[Si](C)(C)C | 2568.3 | Semi standard non polar | 33892256 | Levobunolol,2TMS,isomer #1 | CC(C)(C)N(C[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C)[Si](C)(C)C | 2694.0 | Standard non polar | 33892256 | Levobunolol,2TMS,isomer #1 | CC(C)(C)N(C[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C)[Si](C)(C)C | 2890.1 | Standard polar | 33892256 | Levobunolol,1TBDMS,isomer #1 | CC(C)(C)NC[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C(C)(C)C | 2565.7 | Semi standard non polar | 33892256 | Levobunolol,1TBDMS,isomer #2 | CC(C)(C)N(C[C@H](O)COC1=CC=CC2=C1CCCC2=O)[Si](C)(C)C(C)(C)C | 2798.8 | Semi standard non polar | 33892256 | Levobunolol,2TBDMS,isomer #1 | CC(C)(C)N(C[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3054.8 | Semi standard non polar | 33892256 | Levobunolol,2TBDMS,isomer #1 | CC(C)(C)N(C[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3140.8 | Standard non polar | 33892256 | Levobunolol,2TBDMS,isomer #1 | CC(C)(C)N(C[C@@H](COC1=CC=CC2=C1CCCC2=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3039.3 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Levobunolol GC-MS (Non-derivatized) - 70eV, Positive | splash10-08gi-9540000000-243680d4a0d98a06ee5e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Levobunolol GC-MS (1 TMS) - 70eV, Positive | splash10-08mu-9423000000-24d9e3e549ee0f3caefc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Levobunolol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 10V, Positive-QTOF | splash10-0006-1290000000-a27d598a50efb04fd09e | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 20V, Positive-QTOF | splash10-000i-9470000000-fade873eb3e9b9280e3f | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 40V, Positive-QTOF | splash10-0079-9400000000-9c86007a0342c84063d9 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 10V, Negative-QTOF | splash10-01ox-1690000000-01bd12a64aa5a1ac1b0c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 20V, Negative-QTOF | splash10-03di-0900000000-f14eecc41eae40c5ae10 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 40V, Negative-QTOF | splash10-03di-3900000000-bd973c4edbfdfc4ff33c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 10V, Positive-QTOF | splash10-0006-0090000000-528baf592ca874e0be73 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 20V, Positive-QTOF | splash10-022l-3490000000-47baa556e9ab27cc0b6b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 40V, Positive-QTOF | splash10-0a4i-9400000000-0bc68579194e5bf27651 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 10V, Negative-QTOF | splash10-0006-0290000000-23bba37d597734cfc791 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 20V, Negative-QTOF | splash10-03dl-1910000000-29bcb195f7a66d163c96 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Levobunolol 40V, Negative-QTOF | splash10-01oy-0900000000-698fee7bcd270c336dab | 2021-10-11 | Wishart Lab | View Spectrum |
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General References | - Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [PubMed:2891463 ]
- Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61. [PubMed:2892662 ]
- Novack GD: Levobunolol for the long-term treatment of glaucoma. Gen Pharmacol. 1986;17(4):373-7. [PubMed:3019819 ]
- Leung M, Grunwald JE: Short-term effects of topical levobunolol on the human retinal circulation. Eye (Lond). 1997;11 ( Pt 3):371-6. [PubMed:9373479 ]
- 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. [PubMed:10443129 ]
- 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. [PubMed:14576520 ]
- 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. [PubMed:17459374 ]
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