Timolol

Base Information

• Chemical Name: Timolol
• CAS No.: 26839-75-8
• Deprecated CAS: 131628-37-0,194288-09-0
• Molecular Formula: C13H24N4O3S
• Molecular Weight: 316.425
• European Community (EC) Number: 248-032-6
• UNII: 5JKY92S7BR
• DSSTox Substance ID: DTXSID4023674
• Nikkaji Number: J10.426D
• Wikipedia: Timolol
• Wikidata: Q413994
• NCI Thesaurus Code: C90802
• RXCUI: 1546004
• Pharos Ligand ID: 952J8AXNZB3W
• Metabolomics Workbench ID: 50028
• ChEMBL ID: CHEMBL499
• Mol file: 26839-75-8.mol

Synonyms:(S)-1-((1,1-Dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadazol-3-yl)oxy)-2-propanol;2-Propanol, 1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-, (S)-;Blocadren;L 714,465;L-714,465;L714,465;MK 950;MK-950;MK950;Optimol;Timacar;Timolol;Timolol Hemihydrate;Timolol Maleate;Timolol Maleate, (1:1) Salt;Timoptic;Timoptol

Chemical Property of Timolol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.62E-10mmHg at 25°C
• Melting Point: 71.5 - 72.5oC
• Refractive Index: 1.548
• Boiling Point: 487.2 °C at 760 mmHg
• PKA: pKa ～9.2(H2O t = 25.0) (Uncertain)
• Flash Point: 248.5 °C
• PSA: 107.98000
• Density: 1.224 g/cm³
• LogP: 0.95840
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 316.15691181
• Heavy Atom Count: 21
• Complexity: 310

Purity/Quality:

99% ^*data from raw suppliers

(S)-Timolol-d9Maleate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CC(C)(C)NCC(COC1=NSN=C1N2CCOCC2)O
• Isomeric SMILES: CC(C)(C)NC[C@@H](COC1=NSN=C1N2CCOCC2)O
• Recent ClinicalTrials: PRO-122 Versus Concomitant Therapy in Subjects With Uncontrolled Primary Open-angle Glaucoma (PRO-122LATAM)
• Recent EU Clinical Trials: The influence of Timolol Nasal Spray on Epistaxis in Hereditary Hemorrhagic Telangiectasia (HHT)
• Recent NIPH Clinical Trials: Long term treatment study of 0.02% STN1013900 ophthalmic solution alone or in combination with either 0.005% Latanoprost ophthalmic solution, or 0.5%Timolol ophthalmic solution in subjects with open angle glaucoma or ocular hypertension
• Uses: Timolol is a nonselective β-adrenoblocker that prevents action of catecholamines. When used locally in the form of eye drops, intraocular pressure decreases. It is used for chronic open-angle glaucoma as well as closed-angle glaucoma. Betimol(Sanofi Winthrop). Timolol is a β-adrenergic blocker most commonly used to treat raised blood pressure; used to treat angina (pain from inadequate oxygen supply to the heart muscle); treatment of so me disturbances of heart rhythm; used to prevent migraine headaches; drops treat some types of glaucoma (raised pressure within the eye).
• Therapeutic Function: Antiarrhythmic, Antiglaucoma

Technology Process of Timolol

There total 20 articles about Timolol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

→ timolol (26839-75-8,47148-57-2)

Guidance literature:

Reference yield: 90.0%

(S)-5-((4-morpholino-1,2,5-thiadiazol-3-yloxy)-methyl)-3-tert-butyloxazolidin-2-one (56526-15-9) → timolol (26839-75-8,47148-57-2)

Guidance literature:

With sodium hydroxide; In methanol; for 8h;

DOI:10.1016/j.tet.2007.01.057

Reference yield: 85.0%

timolol maleate (26921-17-5) → timolol (26839-75-8,47148-57-2)

Guidance literature:

With sodium hydroxide; In water; at 0 - 5 ℃; for 0.25h;

upstream raw materials:

3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole

tert-butyl({[(2S)-oxiran-2-yl]methyl})amine

3-Morpholino-4-chloro-1,2,5-thiadiazole

((2Ξ,5S)-3-tert-butyl-2-phenyl-oxazolidin-5-yl)-methanol

Downstream raw materials:

timolol maleate

1-(tert-butylamino)-3-(4-morpholino-1,2,5-thiadiazol-3-yloxy)propan-2-yl 4-(3-thioxo-3H-1,2-dithiol-4-yl)benzoate

C₂₀H₃₈N₄O₆S

3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole

Refernces

• 1、 Narina, Srinivasarao V.,Sudalai, Arumugam. "Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines". . p. 3026 - 3030. Retrieved 2007.
• 2、 Bredikhina,Pashagin,Savel'ev,Bredikhin. "New approach to nonracemic 1-alkylamino-3-aryloxypropan-2-ols belonging to β-blockers via cyclic sulfites". . p. 436 - 439. Retrieved 2001.
• 3、 -. "DRUGS AND COMPOSITIONS FOR THE TREATMENT OF OCULAR DISORDERS". Page/Page column 279. . Retrieved 2018/10/19.
• 4、 Ali, Imran,Saleem, Kishwar,Gaitonde, Vinay D.,Aboul-Enein, Hassan Y.,Hussain, Iqbal. "Chiral separations of some β-adrenergic agonists and antagonists on AmyCoat column by HPLC". experimental part. p. 24 - 28. Retrieved 2010/09/14.