Timolol

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Timolol
Timolol Structural Formulae.png
Timolol ball-and-stick.png
Systematic (IUPAC) name
(S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
Clinical data
Trade names Timoptic
AHFS/Drugs.com monograph
MedlinePlus a602022
Pregnancy cat. C (AU) C (US)
Legal status Prescription only
Routes oral, Ophthalmic
Pharmacokinetic data
Bioavailability 60%
Metabolism Hepatic: 80%
Half-life 2.5-5 hours
Excretion Renal
Identifiers
CAS number 26839-75-8 YesY
ATC code C07AA06 S01ED01
PubChem CID 33624
IUPHAR ligand 565
DrugBank DB00373
ChemSpider 31013 YesY
UNII 5JKY92S7BR YesY
KEGG D08600 YesY
ChEBI CHEBI:9599 YesY
ChEMBL CHEMBL499 YesY
Chemical data
Formula C13H24N4O3S 
Mol. mass 316.421 g/mol
 YesY (what is this?)  (verify)

Timolol maleate is a non-selective beta-adrenergic receptor antagonist indicated for treating glaucoma, heart attacks and hypertension.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.[1]

Medical uses[edit]

In its oral form, it is used:

In its ophthalmic form it is used to treat open-angle and occasionally secondary glaucoma by reducing aqueous humour production through blockage of the beta receptors on the ciliary epithelium. The pharmacological mechanism by which it actually does this is still unknown. First beta-blocker approved for topical use in treatment of glaucoma in the USA (1978). With monotherapy, depresses IOP 18-34% below baseline within first few treatments. However, there are short-term escape and long-term drift effects in some patients. That is, tolerance develops. May reduce extent of diurnal IOP curve up to 50%. IOP higher during sleep. 5-10x more potent beta-blocker than propranolol. Light sensitive; preserved with 0.01% benzalkonium Cl (and also comes BAC free). Can also be used in adjunctive therapy with pilocarpine or CAIs.

The 20 January 2014, issue of the Medical Journal of Australia (MJA) reported on topical timolol being successfully used to treat chronic leg ulcers in 92-year-old patient. <1>

A Cochrane Systematic Review compared the effect of timolol versus brimonidine in slowing the progression of open angle glaucoma in adult participants.[3]

Side effects[edit]

The most serious possible side effects include cardiac arrhythmias and severe bronchospasms. Timolol can also lead to fainting, congestive heart failure, depression, confusion, worsening of Raynaud's syndrome and impotence.

Formulations[edit]

  • Gel-forming solution, ophthalmic, as maleate (Timoptic-XE): 0.25% (2.5 mL, 5 mL); 0.5% (2.5 mL, 5 mL)
  • Solution, ophthalmic, as hemihydrate (Betimol): 0.25% (5 mL, 10 mL, 15 mL); 0.5% (5 mL, 10 mL, 15 mL) [contains benzalkonium chloride]
  • Solution, ophthalmic, as maleate: 0.25% (5 mL, 10 mL, 15 mL); 0.5% (5 mL, 10 mL, 15 mL) [contains benzalkonium chloride]
  • Timoptic: 0.25% (5 mL, 10 mL); 0.5% (5 mL, 10 mL) [contains benzalkonium chloride]
  • Solution, ophthalmic, as maleate [preservative free] (Timoptic OcuDose): 0.25% (0.2 mL);0.5% (0.2 mL) [single use]
  • Tablet, as maleate (Blocadren): 5 mg, 10 mg, 20 mg

For ophthalmic use, timolol is also available combined with other medications:

Brand names[edit]

  • In Canada: Apo-Timol, Apo-Timop, Gen-Timolol, Nu-Timolol, Phoxal-timolol, PMS-Timolol, Tim-AK, Timoptic, Timoptic-XE.
  • In the United States: Betimol, Blocadren, Istalol, Timoptic, Timoptic-XE, Timoptic OcuDose.
  • In Jordan:Apimol ( By API )[4]
  • IOTIM is No. 1 prescribed brand in INDIA from FDC LIMITED .

Chemical synthesis[edit]

Timolol synthesis.[5]

References[edit]

  1. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  2. ^ Dawn A. Marcus; Philip A. Bain (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. Retrieved 14 November 2010. 
  3. ^ Sena DF, Lindsley K (2013). "Neuroprotection for treatment of glaucoma in adults". Cochrane Database Syst Rev 2: CD006539. doi:10.1002/14651858.CD006539.pub3. PMID 20166085. 
  4. ^ http://www.jfda.jo/
  5. ^ doi:10.1021/jo00881a011
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External links[edit]