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{{Drugbox
| verifiedrevid = 457286138
| IUPAC_name = (''S'')-1-(''tert''-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
| image = Timolol Structural Formulae.png
| image2 =Timolol ball-and-stick.png
<!--Clinical data-->
| tradename = Timoptic
| Drugs.com = {{drugs.com|monograph|timolol-eent}}
| MedlinePlus = a602022
| pregnancy_AU = C
| pregnancy_US = C
| legal_status = Rx-only
| routes_of_administration = oral, [[human eye|Ophthalmic]]
<!--Pharmacokinetic data-->
| bioavailability = 60%
| metabolism = [[Liver|Hepatic]]: 80%
| elimination_half-life = 2.5-5 hours
| excretion = [[Kidney|Renal]]
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 26839-75-8
| ATC_prefix = C07
| ATC_suffix = AA06
| ATC_supplemental = {{ATC|S01|ED01}}
| PubChem = 33624
| IUPHAR_ligand = 565
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00373
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 31013
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5JKY92S7BR
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08600
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9599
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 499
<!--Chemical data-->
| C=13 | H=24 | N=4 | O=3 | S=1
| molecular_weight = 316.421 g/mol
| smiles = O[C@H](COc1nsnc1N2CCOCC2)CNC(C)(C)C
| InChI = 1/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
| InChIKey = BLJRIMJGRPQVNF-JTQLQIEIBV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BLJRIMJGRPQVNF-JTQLQIEISA-N
}}
__NOTOC__
__NOTOC__
{{Timolol}}
{{Timolol}}
Line 8: Line 62:


==Overview==
==Overview==
'''Timolol maleate'''  is a non-selective [[beta blocker|beta-adrenergic receptor antagonist]] indicated for treating [[glaucoma]], [[myocardial infarction|heart attacks]] and [[hypertension]].


==Category==
==Category==
Line 31: Line 87:


==Mechanism of Action==
==Mechanism of Action==
==Uses==
In its oral form ('''Blocadren'''), it is used:
* to treat [[hypertension|high blood pressure]]
* to prevent [[myocardial infarction|heart attack]]s
* to prevent [[migraine]] headaches<ref name="MarcusBain2009">{{cite book|author1=Dawn A. Marcus|author2=Philip A. Bain|title=Effective Migraine Treatment in Pregnant and Lactating Women: A Practical Guide|url=http://books.google.com/books?id=Z5YWpjj89NEC&pg=PA141|accessdate=14 November 2010|date=27 February 2009|publisher=シュプリンガー・ジャパン株式会社|isbn=978-1-60327-438-8|pages=141–}}</ref>
In its [[human eye|ophthalmic]] form (brand names '''Timoptol''' in Italy; '''Timoptic'''), 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 [[Intraocular pressure|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.
==Side effects==
The most serious possible side effects include cardiac [[arrhythmia]]s and severe [[bronchospasm]]s. Timolol can also lead to [[Syncope (medicine)|fainting]], [[congestive heart failure]], [[clinical depression|depression]], [[confusion]], worsening of [[Raynaud's syndrome]] and [[impotence]].
==Usual dosage==
*Children and Adults: Ophthalmic: Initial: 0.25% solution, instill 1 drop twice daily; increase to 0.5% solution if response not adequate; decrease to 1 drop/day if *controlled; do not exceed 2 drops twice daily of 0.5% solution Adults: Oral:
*Hypertension: Initial: 10&nbsp;mg twice daily, increase gradually every 14 days, usual dosage: 20–40&nbsp;mg/day in 2 divided doses; maximum: 60&nbsp;mg/day
*Prevention of myocardial infarction: 10&nbsp;mg twice daily initiated within 1–6 weeks after infarction
*Migraine headache: Initial: 10&nbsp;mg twice daily, increase to maximum of 30&nbsp;mg/day
==Formulations==
*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&nbsp;mg, 10&nbsp;mg, 20&nbsp;mg
For ophthalmic use, timolol is also available combined with other medications:
*[[Combigan]] - timolol and [[brimonidine]]
*IOTIM-B - timolol and brimonidine
*[[Cosopt]] - timolol maleate and [[Dorzolamide|dorzolamide hydrochloride]]
*[[Alcon#Glaucoma|DuoTrav]] - timolol and [[travoprost]]
*XOalacom (Pfizer) - timolol and latanoprost
==Brand names==
*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''''' )<ref>http://www.jfda.jo/</ref>
* IOTIM is No. 1 prescribed brand in INDIA from FDC LIMITED.
==Chemical synthesis==
[[File:Timolol 2.png|500px]]


==References==
==References==
{{Reflist|2}}


{{Reflist|2}}
{{Beta blockers}}
{{Antiglaucoma preparations and miotics}}


[[Category:Beta blockers]]
[[Category:Morpholines]]
[[Category:World Health Organization essential medicines]]
[[Category:Thiadiazoles]]
[[Category:Alcohols]]
[[Category:Ethers]]
[[Category:Cardiovascular Drugs]]
[[Category:Cardiovascular Drugs]]
[[Category:Antimigraine Drugs]]
[[Category:Antimigraine Drugs]]
[[Category:Drugs]]
[[Category:Drugs]]

Revision as of 20:07, 7 February 2014

Timolol (tablet)
Clinical data
Trade namesTimoptic
AHFS/Drugs.comMonograph
MedlinePlusa602022
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
Routes of
administration		oral, Ophthalmic
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability60%
MetabolismHepatic: 80%
Elimination half-life2.5-5 hours
ExcretionRenal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC13H24N4O3S
Molar mass316.421 g/mol
3D model (JSmol)
  (verify)
Timolol
TIMOLOL MALEATE® FDA Package Insert
Indications and Usage
Dosage and Administration
Contraindications
Warnings and Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Overdosage
Description
Clinical Pharmacology
How Supplied/Storage and Handling
Labels and Packages
Clinical Trials on Timolol
ClinicalTrials.gov

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

For patient information about Timolol Tablet, click here

Synonyms / Brand Names:

Overview

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

Category

FDA Package Insert

Indications and Usage | Dosage and Administration | Dosage Forms and Strengths | Contraindications | Warnings and Precautions | Adverse Reactions | Drug Interactions | Use in Specific Populations | Overdosage | Description | Clinical Pharmacology | Nonclinical Toxicology | Clinical Studies | How Supplied/Storage and Handling | Patient Counseling Information | Labels and Packages

Mechanism of Action

Uses

In its oral form (Blocadren), it is used:

In its ophthalmic form (brand names Timoptol in Italy; Timoptic), 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.

Side effects

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.

Usual dosage

  • Children and Adults: Ophthalmic: Initial: 0.25% solution, instill 1 drop twice daily; increase to 0.5% solution if response not adequate; decrease to 1 drop/day if *controlled; do not exceed 2 drops twice daily of 0.5% solution Adults: Oral:
  • Hypertension: Initial: 10 mg twice daily, increase gradually every 14 days, usual dosage: 20–40 mg/day in 2 divided doses; maximum: 60 mg/day
  • Prevention of myocardial infarction: 10 mg twice daily initiated within 1–6 weeks after infarction
  • Migraine headache: Initial: 10 mg twice daily, increase to maximum of 30 mg/day

Formulations

  • 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

  • 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 )[2]
  • IOTIM is No. 1 prescribed brand in INDIA from FDC LIMITED.

Chemical synthesis

File:Timolol 2.png

References

  1. ↑ 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.
  2. ↑ http://www.jfda.jo/

Template:Antiglaucoma preparations and miotics

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