Levobunolol

Levobunolol
Names
Trade namesAKBeta, Betagan, Vistagan, others
Other namesLevobunolol hydrochloride
IUPAC name
  • (S)-5-{[3-(tert-Butylamino)-2-hydroxypropyl]oxy}-3,4-dihydronaphthalen-1(2H)-one
Clinical data
Drug classBeta blocker[1]
Main usesIncreased intraocular pressure[1]
Side effectsEye redness and stinging[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • C
Routes of
use		Topical (eye drops)
Onset of action≤ 1 hour
Duration of actionUp to 16 hours
External links
AHFS/Drugs.comMonograph
MedlinePlusa686011
Legal
Legal status
Pharmacokinetics
Bioavailability7.5% (rabbit eye)
Metabolitesdihydrolevobunolol (equally active)
Elimination half-life6 hours[2]
Excretionmostly renal
Chemical and physical data
FormulaC17H25NO3
Molar mass291.391 g·mol−1
3D model (JSmol)
Melting point209 to 211 °C (408 to 412 °F) (hydrochloride)
Solubility in watersoluble (hydrochloride)
SMILES
  • O=C2c1cccc(OC[C@@H](O)CNC(C)(C)C)c1CCC2
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 checkY
  • Key:IXHBTMCLRNMKHZ-LBPRGKRZSA-N checkY

Levobunolol , sold under the brand name Betagan among others, is a medication used to treat increased intraocular pressure and open-angle glaucoma.[1] It is used as an eye drop.[1] It decreases pressure by about 25 to 40%.[1]

Common side effects include redness and stinging of the eye.[1] Other side effects may include bacterial keratitis and low blood pressure.[1] It is a non-selective beta blocker.[1]

Levobunolol was approved for medical use in the United States in 1985.[1] In the United Kingdom 30 doses cost the NHS about £10 as of 2021.[3] In the United States 5 ml costs about 12 USD.[4]

Medical use

Dosage

It is used once to twice per day.[3]

Contraindications

Like other beta blockers, levobunolol is contraindicated in patients with airway diseases such as asthma and severe chronic obstructive pulmonary disease (COPD), as well as heart problems such as sinus bradycardia, second- or third-degree atrioventricular block, sick sinus syndrome, and cardiogenic shock.[5][6] Combination with MAO-A inhibitors is also contraindicated because it could cause a dangerous rise in blood pressure.[2]

Levobunolol is not useful for the treatment of closed-angle glaucoma.[2]

Side effects

Further information: Beta blocker § Adverse effects

The most common side effect is eye irritation felt as stinging or burning, which occurs in up to a third of patients. Blepharoconjunctivitis occurs in up to 5% of patients. Rarer adverse effects include keratitis, edema and increased lacrimation.[5][6] Allergies are rare, but seem to be more common than under the related drug timolol.[2]

If the substance reaches the nasal mucosa via the tear duct, it can be absorbed into the bloodstream and cause systemic side effects. These include orthostatic hypotension (low blood pressure) and other effects on the heart and circulatory system, breathing problems in people with asthma, and skin symptoms such as itching and aggravation of psoriasis.[2]

Interactions

Even in the form of eye drops, levebunolol may cause hypotension when combined with alpha blockers, calcium channel blockers, tricyclic antidepressants, and other drugs that lower blood pressure. It can also cause severe hypertension (high blood pressure) when combined with sympathomimetic drugs or MAO-A inhibitors, bradycardia (low heart rate) when combined with antiarrhythmics or mefloquine, and hypoglycemia (low blood sugar) when combined with antidiabetic drugs such as insulin.[2]

Pharmacology

Dihydrolevobunolol, the metabolite, which has equal activity to levobunolol[2]

Mechanism of action

Levobunolol is a non-cardioselective beta blocker, that is, it blocks beta-1 receptors as well as beta-2 receptors. The latter type dominates in the ciliary body, where it controls aqueous humour production. Blocking this type of receptor reduces aqueous humour production, lowering intraocular pressure. The substance has no relevant membrane stabilizing effect or intrinsic sympathomimetic activity. Like other beta blockers, and unlike the anti-glaucoma medication pilocarpine, levobunolol has no effect on accommodation and pupil size.[5][7]

Pharmacokinetics

The substance quickly penetrates the cornea and reaches the aqueous humour. It is reduced to dihydrolevobunolol, which is equally active, in the eye's tissues. The drug starts to lower intraocular pressure within an hour, reaches its maximum effect after two to six hours, and remains effective for up to 16 hours. It has an elimination half-life of six hours and is mainly excreted via the kidney.[2][5]

Chemistry

Levobunolol is the pure L-enantiomer of bunolol and has more than 60 times the pharmacological activity of D-bunolol.[5] It is used as the hydrochloride, which melts at 209 to 211 °C (408 to 412 °F) and is soluble in water and methanol and slightly soluble in ethanol.[2]

References

  1. 1 2 3 4 5 6 7 8 9 10 "Levobunolol Monograph for Professionals". Drugs.com. Archived from the original on 25 January 2021. Retrieved 21 November 2021.
  2. 1 2 3 4 5 6 7 8 9 Dinnendahl, V; Fricke, U, eds. (2011). Arzneistoff-Profile (in German). Vol. 6 (25 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.{{cite book}}: CS1 maint: unrecognized language (link)
  3. 1 2 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 1225. ISBN 978-0857114105.
  4. ↑ "Levobunolol Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 14 October 2016. Retrieved 21 November 2021.
  5. 1 2 3 4 5 Haberfeld, H (ed.). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.{{cite book}}: CS1 maint: unrecognized language (link)
  6. 1 2 FDA Professional Drug Information on levobunolol.
  7. ↑ Mutschler, Ernst (2012). Arzneimittelwirkungen (in German) (10 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 781. ISBN 978-3-8047-2898-1.{{cite book}}: CS1 maint: unrecognized language (link)
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