Timolol

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Timolol
Clinical data
Trade namesTimoptic, others[1]
AHFS/Drugs.comMaleate Monograph
eent Monograph
MedlinePlusa684029
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, topical (eye drop)
Drug classBeta blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60%
MetabolismLiver (80%, mainly CYP2D6[4])
Onset of action15–30 min[3]
Elimination half-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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
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 a beta blocker medication used either by mouth or as eye drops.[3][5] As eye drops it is used to treat increased pressure inside the eye such as in ocular hypertension and glaucoma.[3] By mouth it is used for high blood pressure, chest pain due to insufficient blood flow to the heart, to prevent further complications after a heart attack, and to prevent migraines.[5]

Common side effects with the drops is irritation of the eye.[3] Common side effects by mouth include tiredness, slow heart beat, itchiness, and shortness of breath.[5] Other side effects include masking the symptoms of low blood sugar in those with diabetes.[3] Use is not recommended in those with asthma, uncompensated heart failure, or chronic obstructive pulmonary disease (COPD).[3] It is unclear if use during pregnancy is safe for the fetus.[6] Timolol is a non-selective beta blocker.[3]

Timolol was patented in 1968, and came into medical use in 1978.[7] It is on the World Health Organization's List of Essential Medicines.[8] Timolol is available as a generic 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

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By mouth

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

The combination of timolol and the alpha-1 blocker prazosin has sedative effects.[13]

Eye drops

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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 first beta blocker approved for topical use in treatment of glaucoma in the United States (1978).[15] When used by itself, it depresses intraocular 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 than propranolol. 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 with pilocarpine, carbonic anhydrase inhibitors[19] or prostaglandin analogs.[20]

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

On the skin

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

Available forms

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

For ophthalmic use, timolol is also available combined:

Contraindications

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

Side effects

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The most serious possible side effects include cardiac arrhythmias and severe bronchospasms.[23] Timolol can also lead to fainting, congestive heart failure, depression, confusion, worsening of Raynaud's syndrome and impotence.[23]

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

Chemistry

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

Society and culture

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Brand names

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

References

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