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Prestwick3_000847

Prestwick3_000847

Synopsis, Chemistry

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SOLUTION/DROPS;OPHTHALMIC - 0.5%, SOLUTION/DROPS;OPHTHALMIC - 0.25% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

SOLUTION/DROPS;OPHTHALMIC - 0.5%
SOLUTION/DROPS;OPHTHALMIC - 0.25% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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Also known as: 47141-42-4, Levobunololum, (-)-bunolol, Levobunololum [inn-latin], Levobunolol (inn), Levobunolol hydrochloride

Molecular Formula

C₁₇H₂₅NO₃

Molecular Weight

291.4 g/mol

InChI Key

IXHBTMCLRNMKHZ-LBPRGKRZSA-N

FDA UNII

G6317AOI7K

The L-Isomer of bunolol.

Levobunolol is a beta-Adrenergic Blocker. The mechanism of action of levobunolol is as an Adrenergic beta-Antagonist.

1 2D Structure

Prestwick3_000847

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

IXHBTMCLRNMKHZ-LBPRGKRZSA-N

2.1.4 Canonical SMILES

CC(C)(C)NCC(COC1=CC=CC2=C1CCCC2=O)O

2.1.5 Isomeric SMILES

CC(C)(C)NC[C@@H](COC1=CC=CC2=C1CCCC2=O)O

2.2 Other Identifiers

2.2.1 UNII

G6317AOI7K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Akbeta

2. Apo Levobunolol

3. Apo-levobunolol

4. Apolevobunolol

5. Betagan

6. Levobunolol Hydrochloride

7. Novo Levobunolol

8. Novo-levobunolol

9. Novolevobunolol

10. Pms Levobunolol

11. Pms-levobunolol

12. Pmslevobunolol

13. Ratio Levobunolol

14. Ratio-levobunolol

15. Ultracortenol

16. Vistagan

17. W 7000a

18. W-7000a

19. W7000a

2.3.2 Depositor-Supplied Synonyms

1. 47141-42-4

2. Levobunololum

3. (-)-bunolol

4. Levobunololum [inn-latin]

5. Levobunolol (inn)

6. Levobunolol Hydrochloride

7. (s)-5-(3-(tert-butylamino)-2-hydroxypropoxy)-3,4-dihydronaphthalen-1(2h)-one

8. Bunolol, (s)-

9. Bunolol, (-)-

10. 5-[(2s)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2h-naphthalen-1-one

11. Chebi:6438

12. G6317aoi7k

13. Levobunolol [inn]

14. Levobunolol [inn:ban]

15. (s)-5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2h)-naphthalenone

16. L-bunolol

17. Ccris 4375

18. Ncgc00016801-01

19. Cas-27912-14-7

20. Liquifilm

21. Unii-g6317aoi7k

22. (-)-levobunolol Hydrochloride

23. Beta-site

24. Ak-beta

25. W-6421a

26. Brn 1887243

27. Levobunolol [mi]

28. Prestwick0_000847

29. Prestwick1_000847

30. Prestwick2_000847

31. Prestwick3_000847

32. Levobunolol [vandf]

33. 1(2h)-naphthalenone, 5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-, (s)-

34. 5-[(2s)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydronaphthalen-1(2h)-one

35. Schembl24095

36. Bspbio_000833

37. Gtpl570

38. Levobunolol [who-dd]

39. Spbio_002754

40. Bpbio1_000917

41. Chembl1201237

42. Dtxsid1043833

43. Hy-b1035a

44. Zinc3830339

45. Db01210

46. Ncgc00016801-02

47. Ncgc00016801-03

48. Cas-47141-41-3

49. Cs-0013643

50. C07914

51. D08115

52. Q408556

53. Brd-k31812033-003-03-7

54. (-)-(s)-5-(3-(tert-butylamino)-2-hydroxypropoxy)-3,4-dihydro-1(2h)-naphthalenone

55. 5-[(2s)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₅NO₃
Molecular Weight	291.4 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	291.18344366 g/mol
Monoisotopic Mass	291.18344366 g/mol
Topological Polar Surface Area	58.6 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	350
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Akbeta
PubMed Health	Levobunolol (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	BETAGAN (levobunolol hydrochloride ophthalmic solution, USP) sterile is a noncardioselective beta-adrenoceptor blocking agent for ophthalmic use. The solution is colorless to slightly light yellow in appearance with an osmolality range of 250-360 m...
Active Ingredient	Levobunolol hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 0.25%
Market Status	Prescription
Company	Akorn

2 of 4
Drug Name	Betagan
Active Ingredient	Levobunolol hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 0.25%
Market Status	Prescription
Company	Allergan

3 of 4
Drug Name	Akbeta
PubMed Health	Levobunolol (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	BETAGAN (levobunolol hydrochloride ophthalmic solution, USP) sterile is a noncardioselective beta-adrenoceptor blocking agent for ophthalmic use. The solution is colorless to slightly light yellow in appearance with an osmolality range of 250-360 m...
Active Ingredient	Levobunolol hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 0.25%
Market Status	Prescription
Company	Akorn

4 of 4
Drug Name	Betagan
Active Ingredient	Levobunolol hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 0.25%
Market Status	Prescription
Company	Allergan

4.2 Drug Indication

For lowering intraocular pressure (IOP) and may be used in patients with chronic open-angle glaucoma or ocular hypertension.

FDA Label

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Sympatholytics

Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here. (See all compounds classified as Sympatholytics.)

Adrenergic beta-Antagonists

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety. (See all compounds classified as Adrenergic beta-Antagonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

LEVOBUNOLOL

5.3.2 FDA UNII

G6317AOI7K

5.3.3 Pharmacological Classes

beta-Adrenergic Blocker [EPC]; Adrenergic beta-Antagonists [MoA]

5.4 ATC Code

S01ED03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01ED - Beta blocking agents

S01ED03 - Levobunolol

5.5 Absorption, Distribution and Excretion

Absorption

80%

5.6 Metabolism/Metabolites

Hepatic

5.7 Biological Half-Life

20 hours

5.8 Mechanism of Action

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.