(S)-Timolol (CHEM016910)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:47:21 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016910
Identification
Common Name(S)-Timolol
ClassSmall Molecule
DescriptionTimolol is a nonselective beta-adrenergic antagonist given in an eye drop solution to reduce intraocular pressure, or pressure in the eyes. It is also used in tablet form as a drug to treat hypertension. Timolol was first approved by the FDA in 1978. This drug is marketed by several manufacturers and is an effective agent for the management of conditions such as open-angle glaucoma and hypertension.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-3-Morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazoleChEBI
(2S)-1-((1,1-Dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-2-propanolChEBI
(S)-1-(1,1-(Dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-2-propanolChEBI
(S)-1-(Tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-olChEBI
(S)-1-Tert-butylamino-3-(4-morpholin-4-yl-[1,2,5]thiadiazol-3-yloxy)-propan-2-olChEBI
(S)-TimololChEBI
1-(Tert-butylamino)-3-[4-(1,4-oxazinan-4-yl)-1,2,5-thiadiazol-3-yloxy]-(2S)-propan-2-olChEBI
S-(-)-3-(3-Tert-butylamino-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazoleChEBI
BetimolKegg
TimololChEBI
(S)-1-((1,1-Dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadazol-3-yl)oxy)-2-propanolMeSH
TimacarMeSH
OptimolMeSH
Timolol hemihydrateMeSH
BlocadrenMeSH
Timolol maleate, (1:1) saltMeSH
TimopticMeSH
TimoptolMeSH
Hemihydrate, timololMeSH
Timolol maleateMeSH
Chemical FormulaC13H24N4O3S
Average Molecular Mass316.420 g/mol
Monoisotopic Mass316.157 g/mol
CAS Registry Number26839-75-8
IUPAC Name(2S)-1-(tert-butylamino)-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}propan-2-ol
Traditional Name(2S)-1-(tert-butylamino)-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}propan-2-ol
SMILES[H][C@](O)(CNC(C)(C)C)COC1=NSN=C1N1CCOCC1
InChI IdentifierInChI=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
InChI KeyBLJRIMJGRPQVNF-JTQLQIEISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Alkyl aryl ether
  • Morpholine
  • Oxazinane
  • Imidolactam
  • Azole
  • Heteroaromatic compound
  • Thiadiazole
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Oxacycle
  • Ether
  • Secondary aliphatic amine
  • Dialkyl ether
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP1.44ALOGPS
logP1.34ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.08ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity83.92 m³·mol⁻¹ChemAxon
Polarizability33.86 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0009000000-d71d621ed511e13fd0fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02t9-0069000000-b1978af1db9940bfb5e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01vx-4390000000-df83be04a7e7c18de424Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9410000000-c9b47edd2cfab49a0aefSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9300000000-617e94c43fe73fa575e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03di-0090000000-da0c1e25ae5110879b00Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-02t9-0379000000-8b822b96645d698d2c82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2449000000-658bdda5490ee521a38aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9572000000-eeff2781c39c4d9bc9acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-9200000000-04646f3c9b1ea6bed03dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2938000000-2af43376de55b5ef3669Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-3921000000-57cfb128498f5b8c8aefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5900000000-7a92e177cc451b3d3eccSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00373
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTimolol
Chemspider IDNot Available
ChEBI ID9599
PubChem Compound IDNot Available
Kegg Compound IDC07141
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10891117
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11300874
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11728183
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11784135
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14971904
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15027870
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15857133
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1635066
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=2002467
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=2579237
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=2872332
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2892933
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2903243
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6094812
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6109024
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=6113285
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=6126588
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=6134834
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=8568799
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=9288160