(S)-1-[(1,1-dimethylethyl)amino]-3-{[4-morpholinyl)-1,2,5-thiadiazol-3yl]oxy}-2-propanol.
Timolol maleate
The structural formula
UV - spectrum
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| Conditions : Concentration - 3 mg / 100 ml | ||||
| Solvent designation schedule | Methanol  | Water  | 0.1 M HCl  | 0.1M NaOH  |
|---|---|---|---|---|
| The absorption maximum | 299 nm | - | 295 nm | 296 nm |
 | 210 | - | 197 | 206 |
| ε | 9070 | - | 8540 | 8920 |
IR - spectrum
| Wavelength (μm) |
|---|
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| Wavenumber (cm -1 ) |
Mass Spectrum
| Spectrum (for the base) | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|
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| The 10 largest peaks: | ||||||||||
| Peak | 30 | 41 | 56 | 57 | 70 | 74 | 86 | 114 | 128 | 130 |
| Meaning | 376 | 85 | 107 | 168 | 72 | 144 | 999 | 102 | 83 | 214 |
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The crystal structure for S-timolol hemihydrate (single crystals from water-methylene chloride) was measured with a Enraf-Nonius CAD-4 diffractometer using graphite-monochromatized MoK.sub.α (0.71073 Å) and ω-2θ method at 21° C. The cell parameters and orientation matrix were determined from 18 reflections (6<θ<10°). The measuring rate (° min-1) was 0.87-16.5, width (θ) 0.5+0.344tan θ and area (θ) 2-25. The following crystal data were obtained: spaced group monoclinic, C2 (No. 5); a=23.435(3) Å, b=6.384(8) Å, c=11.591(1) Å, α=90.00, β=103.081(1), γ=90.00, V=1687(3) Å, Z=2, d=1.281 gcm-3.
The results obtained with a NMR spectrometer support the above obtained X-ray diffraction results (Instrument Bruker AC 250/Aspect 3000). 1 H-NMR (solvent CDCl3) δ (ppm): 1.09 (s, 9H), 2.0 (b, appr. 2.5H), 2.57 (d+d, 1H; 12.0 and 8.0 Hz), 2.80 (d+d, 1H; 12.0 and 4.0 Hz), 3.52 (m, 4H), 3.79 (m, 4H), 3.91 (m, 1H), 4.36 (d+d, 1H; 11.1 and 5.8 Hz), 4.47 (d+d, 1H; 11.1 and 4.1 Hz).
13 C NMR (solvent CDCl3) 6 (ppm): 28.91 (g), 50.24 (s), 44.33 (t), 66.10 (d), 72.76 (t), 153.66 (s), 149.78 (s), 47.78 (t), 66.33 (t).
S-timol hemihydrate has also been analyzed thermogravimetrically (Perkin Elmer, TGS-2 thermogravimetric analyzer and attached differential scanning DSC 4 calorimeter). The TG graph indicates splitting off of the hydrate water at about 50° C., the DSC gives a melting point of 53.3° C.
Markku Per alampi, “S-timolol hemihydrate composition and method of preparation therefor.” U.S. Patent US5574035, issued October, 1986.
US5574035
Patents
US 6174524, US 5231095
Links
- UV and IR Spectra. H.-W. Dibbern, RM Muller, E. Wirbitzki, 2002 ECV
- NIST / EPA / NIH Mass Spectral Library 2008
- Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman.Academic Press, 2000.
- Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.
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| 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  |
| ATC code | C07AA06 S01ED01 |
| PubChem | CID 33624 |
| IUPHAR ligand | 565 |
| DrugBank | DB00373 |
| ChemSpider | 31013 |
| UNII | 5JKY92S7BR |
| KEGG | D08600 |
| ChEBI | CHEBI:9599 |
| ChEMBL | CHEMBL499 |
| Chemical data | |
| Formula | C13H24N4O3S |
| Mol. mass | 316.421 g/mol |
SYNTHESIS
AZERBAIJAN
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sindh, pakistan,INSTITUTE OF CHEMISTRY UNIVERSITY OF SINDH JAMSHORO
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jAMSHORO
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INSTITUTE OF CHEMISTRY UNIVERSITY OF SINDH JAMSHOROjAMSHOROFood Festival organized by Institute of English Language and Literature UoS , Jamshoro.
