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Timolol

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Timolol
Clinical data
Trade namesTimoptic, others[1]
AHFS/Drugs.comMaleateMonograph
eentMonograph
MedlinePlusa684029
License data
Pregnancy
category
Routes of
administration
By mouth,topical (eye drop)
Drug classBeta blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60%
MetabolismLiver (80%, mainlyCYP2D6[4])
Onset of action15–30 min[3]
Eliminationhalf-life2.5–5 hours
Duration of action24 hours[3]
ExcretionKidney
Identifiers
  • (S)-1-(tert-Butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.043.651Edit this at Wikidata
Chemical and physical data
FormulaC13H24N4O3S
Molar mass316.42 g·mol−1
3D model (JSmol)
  • CC(C)(C)NCC(O)COc1nsnc1N1CCOCC1
  • InChI=1S/C13H24N4O3S/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17/h10,14,18H,4-9H2,1-3H3/t10-/m0/s1 checkY
  • Key:BLJRIMJGRPQVNF-JTQLQIEISA-N checkY
  (verify)

Timolol is abeta blocker medication used eitherby mouth or aseye drops.[3][5] As eye drops it is used to treat increasedpressure inside the eye such as inocular hypertension andglaucoma.[3] By mouth it is used forhigh blood pressure,chest pain due to insufficient blood flow to the heart, to prevent further complications after aheart attack, and to preventmigraines.[5]

Common side effects with the drops is irritation of the eye.[3] Common side effects by mouth include tiredness,slow heart beat, itchiness, andshortness of breath.[5] Other side effects include masking the symptoms of low blood sugar in those withdiabetes.[3] Use is not recommended in those withasthma, uncompensatedheart failure, orchronic obstructive pulmonary disease (COPD).[3] It is unclear if use during pregnancy is safe for the fetus.[6] Timolol is anon-selective beta blocker.[3]

Timolol was patented in 1968, and came into medical use in 1978.[7] It is on theWorld Health Organization's List of Essential Medicines.[8] Timolol is available as ageneric medication.[3][9] In 2023, it was the 173rd most commonly prescribed medication in the United States, with more than 2 million prescriptions.[10][11]

Medical uses

[edit]

By mouth

[edit]

In its by mouth or oral form, it is used:

The combination of timolol and thealpha-1 blockerprazosin hassedative effects.[13]

Eye drops

[edit]

In its eye drop form it is used to treat open-angle and, occasionally,secondary glaucoma.[3][14] The mechanism of action of timolol is probably the reduction of the formation of aqueous humor[3] in the ciliary body in the eye. It was the firstbeta blocker approved for topical use in treatment of glaucoma in the United States (1978).[15] When used by itself, it depressesintraocular pressure (IOP) 18–34% below baseline within first few treatments. However, there are short-term escape and long-term drift effects in some people. That is, tolerance develops. It may reduce the extent of the daytime IOP curve up to 50%. The IOP is higher during sleep. Efficacy of timolol in lowering IOP during the sleep period may be limited.[16][17][18] It is a 5–10× more potent beta blocker thanpropranolol. Timolol is light-sensitive; it is usually preserved with 0.01%benzalkonium chloride (BAC), but also comes BAC-free. It can also be used in combination withpilocarpine,carbonic anhydrase inhibitors[19] orprostaglandin analogs.[20]

ACochrane review compared the effect of timolol versusbrimonidine in slowing the progression of open angle glaucoma in adults but found insufficient evidence to come to conclusions.[21]

On the skin

[edit]

In its gel form it is used on the skin to treatinfantile hemangiomas.[22]

Available forms

[edit]

It is available in tablet and liquid formulations.[23][24]

For ophthalmic use, timolol is also available combined:

Contraindications

[edit]

The medication should not be taken by individuals with:[23]

Side effects

[edit]

The most serious possible side effects include cardiacarrhythmias and severebronchospasms.[23] Timolol can also lead tofainting,congestive heart failure,depression,confusion, worsening ofRaynaud's syndrome andimpotence.[23]

Side effects when given in the eye include: burning sensation, eye redness, superficial punctate keratopathy, corneal numbness.[24][14]

Chemistry

[edit]

The experimentallog P of timolol is 1.8 and its predicted log P ranges from 0.68 to 1.8.[26][27][28]

Society and culture

[edit]

Brand names

[edit]

Timolol is sold under manybrand names worldwide.[1] Timolol eye drops are sold under the brand names Timoptic and Istalol among others.[29][30]

References

[edit]
  1. ^ab"Timolol".Drugs.com.Archived from the original on 7 March 2016. Retrieved28 December 2016.
  2. ^"Product monograph brand safety updates".Health Canada. February 2024. Retrieved24 March 2024.
  3. ^abcdefghijk"Timolol eent". The American Society of Health-System Pharmacists.Archived from the original on 28 December 2016. Retrieved8 December 2016.
  4. ^Volotinen M, Turpeinen M, Tolonen A, Uusitalo J, Mäenpää J, Pelkonen O (July 2007). "Timolol metabolism in human liver microsomes is mediated principally by CYP2D6".Drug Metabolism and Disposition.35 (7):1135–1141.doi:10.1124/dmd.106.012906.PMID 17431033.S2CID 794764.
  5. ^abc"Timolol Maleate". The American Society of Health-System Pharmacists.Archived from the original on 28 December 2016. Retrieved8 December 2016.
  6. ^"Timolol ophthalmic Use During Pregnancy". The American Society of Health-System Pharmacists.Archived from the original on 28 December 2016. Retrieved28 December 2016.
  7. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery. John Wiley & Sons. p. 460.ISBN 978-3-527-60749-5.Archived from the original on 28 December 2016.
  8. ^The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva:World Health Organization. 2023.hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  9. ^"Competitive Generic Therapy Approvals".U.S.Food and Drug Administration (FDA). 29 June 2023. Archived fromthe original on 29 June 2023. Retrieved29 June 2023.
  10. ^"Top 300 of 2023".ClinCalc.Archived from the original on 12 August 2025. Retrieved12 August 2025.
  11. ^"Timolol Drug Usage Statistics, United States, 2013 - 2023".ClinCalc. Retrieved19 August 2025.
  12. ^Marcus DA, Bain PA (27 February 2009).Effective Migraine Treatment in Pregnant and Lactating Women: A Practical Guide. シュプリンガー・ジャパン株式会社. pp. 141–.ISBN 978-1-60327-438-8.Archived from the original on 5 November 2017. Retrieved14 November 2010.
  13. ^Atkin T, Comai S,Gobbi G (April 2018)."Drugs for Insomnia beyond Benzodiazepines: Pharmacology, Clinical Applications, and Discovery".Pharmacol Rev.70 (2):197–245.doi:10.1124/pr.117.014381.PMID 29487083.S2CID 3578916.
  14. ^ab"Timolol Ophthalmic".MedlinePlus. 15 April 2017. Retrieved31 December 2019.
  15. ^Sambhara D, Aref AA (January 2014)."Glaucoma management: relative value and place in therapy of available drug treatments".Therapeutic Advances in Chronic Disease.5 (1):30–43.doi:10.1177/2040622313511286.PMC 3871276.PMID 24381726.
  16. ^Liu JH, Kripke DF, Weinreb RN (September 2004). "Comparison of the nighttime effects of once-daily timolol and latanoprost on intraocular pressure".American Journal of Ophthalmology.138 (3):389–95.doi:10.1016/j.ajo.2004.04.022.PMID 15364220.
  17. ^Liu JH, Medeiros FA, Slight JR, Weinreb RN (March 2009). "Comparing diurnal and nocturnal effects of brinzolamide and timolol on intraocular pressure in patients receiving latanoprost monotherapy".Ophthalmology.116 (3):449–54.doi:10.1016/j.ophtha.2008.09.054.PMID 19157559.
  18. ^Liu JH, Slight JR, Vittitow JL, Scassellati Sforzolini B, Weinreb RN (September 2016)."Efficacy of Latanoprostene Bunod 0.024% Compared With Timolol 0.5% in Lowering Intraocular Pressure Over 24 Hours".American Journal of Ophthalmology.169:249–257.doi:10.1016/j.ajo.2016.04.019.PMID 27457257.
  19. ^Strohmaier K, Snyder E, Adamsons I (July 1998). "A multicenter study comparing dorzolamide and pilocarpine as adjunctive therapy to timolol: patient preference and impact on daily life".Journal of the American Optometric Association.69 (7):441–51.PMID 9697378.
  20. ^"Ganfort 0.3 mg/ml + 5 mg/ml eye drops, solution - Summary of Product Characteristics (SmPC)".(emc). 20 February 2020. Retrieved1 March 2020.
  21. ^Sena DF, Lindsley K (January 2017)."Neuroprotection for treatment of glaucoma in adults".The Cochrane Database of Systematic Reviews.1 (1) CD006539.doi:10.1002/14651858.CD006539.pub4.PMC 5370094.PMID 28122126.
  22. ^Novoa M, Baselga E, Beltran S, Giraldo L, Shahbaz A, Pardo-Hernandez H, et al. (April 2018)."Interventions for infantile haemangiomas of the skin".The Cochrane Database of Systematic Reviews.2018 (4) CD006545.doi:10.1002/14651858.CD006545.pub3.PMC 6513200.PMID 29667726.
  23. ^abcd"Timolol Maleate tablet".DailyMed. 17 August 2006. Retrieved1 December 2019.
  24. ^ab"Betimol- timolol solution".DailyMed. 18 March 2010. Retrieved1 December 2019.
  25. ^"Package leaflet: Information for the user Timolol"(PDF).hpra.ie. Archived fromthe original(PDF) on 16 August 2018. Retrieved15 August 2018.
  26. ^"Timolol | C13H24N4O3S | CID 33624 - PubChem".pubchem.ncbi.nlm.nih.gov. Retrieved2 August 2025.
  27. ^"(−)-S-Timolol".ChemSpider. 10 June 2024. Retrieved10 July 2025.
  28. ^"Timolol: Uses, Interactions, Mechanism of Action".DrugBank Online. 31 December 1994. Retrieved10 July 2025.
  29. ^"Generic Istalol Availability".Drugs.com. Retrieved20 June 2019.
  30. ^"Istalol".Drugs.com. 1 August 2018. Retrieved19 July 2019.

External links

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