TIMOLOL

(S)-1-[(1,1-dimethylethyl)amino]-3-{[4-morpholinyl)-1,2,5-thiadiazol-3yl]oxy}-2-propanol.

(S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol

Timolol maleate

The structural formula

UV - spectrum

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)
Wavenumber (cm -1 )

Mass Spectrum

Spectrum (for the base)
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

SEE FULL CHAPTER AT

http://books.google.co.in/books?id=tQiZCwMb2jAC&pg=PA641&source=gbs_toc_r&cad=4#v=onepage&q&f=false

OR CLICK

Chapter 15 Timolol Maleate

Profiles of Drug Substances, Excipients and Related ...
books.google.com › Science › Chemistry › Organic



Front Cover. Klaus Florey. Academic Press, Sep 4, 1987 - Science - 770 pages ... Chapter 15 Timolol Maleate. 641. 

http://www.google.com/patents/US5231095

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.

Timolol

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

 doi:10.1021/jo00881a011.

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