5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one

• ChemBase ID: 1080
• Molecular Formular: C17H25NO3
• Molecular Mass: 291.3853
• Monoisotopic Mass: 291.18344367
• SMILES: O(c1c2CCCC(=O)c2ccc1)C[C@@H](O)CNC(C)(C)C
• Canonical SMILES: O[C@H](COc1cccc2c1CCCC2=O)CNC(C)(C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one
• IUPAC Traditional name: levobunolol
• Brand Name: Akbeta; Betagan
• Synonyms: Levobunolol HCl; Levobunololum [INN-Latin]; Levobunolol

Database IDs

• CAS Number: 47141-42-4
• PubChem SID: 160964543; 46507518
• PubChem CID: 39468

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.085866
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.009857
• LogD (pH = 7.4): -0.036677748
• Log P: 2.1826746
• Molar Refractivity: 83.2824 cm^3
• Polarizability: 32.726128 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.06
• LOG S: -3.07
• Solubility (Water): 2.51e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.1

DETAILS

DrugBank - DB01210

• Drug Groups: approved
• Description: A nonselective beta-adrenoceptor antagonist used in the treatment of glaucoma. [PubChem]
• Indication: For lowering intraocular pressure (IOP) and may be used in patients with chronic open-angle glaucoma or ocular hypertension.
• Pharmacology: Levobunolol is an ophthalmic beta-blocker, equally effective at β(1)- and β(2)-receptor sites. Levobunolol reduces both elevated and normal IOP in patients with or without glaucoma. In patients with elevated IOP, levobunolol reduces mean IOP by approximately 25-40% from baseline. As the drug is a nonselective &beta-adrenergic blocking agent, it can produce both systemic pulmonary and cardiovascular effects following topical application to the eye. These effects include adverse pulmonary effects (eg. bronchoconstriction, increased airway resistance), and a decrease in blood pressure and heart rate.
• Toxicity: Bradycardia, hypotension, bronchospasm, and acute cardiac failure, LD₅₀=700 mg/kg (orally in rat).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 80%
• Half Life: 20 hours
• References: 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] ; 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] ; Leung M, Grunwald JE: Short-term effects of topical levobunolol on the human retinal circulation. Eye. 1997;11 ( Pt 3):371-6. [Pubmed] ; 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] ; 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] ; Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [Pubmed] ; Novack GD: Levobunolol for the long-term treatment of glaucoma. Gen Pharmacol. 1986;17(4):373-7. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• 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
• 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
• Leung M, Grunwald JE: Short-term effects of topical levobunolol on the human retinal circulation. Eye. 1997;11 ( Pt 3):371-6. Pubmed
• 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
• 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
• Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. Pubmed
• Novack GD: Levobunolol for the long-term treatment of glaucoma. Gen Pharmacol. 1986;17(4):373-7. Pubmed