CHEBI:9599 - (S)-timolol (anhydrous)

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ChEBI Name (S)-timolol (anhydrous)
ChEBI ID CHEBI:9599
ChEBI ASCII Name (S)-timolol (anhydrous)
Definition The (S)-(−) (more active) enantiomer of timolol. A beta-adrenergic antagonist, both the hemihydrate and the maleate salt are used in the mangement of glaucoma, hypertension, angina pectoris and myocardial infarction, and for the prevention of migraine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:108531, CHEBI:108311
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Formula C13H24N4O3S
Net Charge 0
Average Mass 316.42000
Monoisotopic Mass 316.157
InChI InChI=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
InChIKey BLJRIMJGRPQVNF-JTQLQIEISA-N
SMILES CC(C)(C)NC[C@H](O)COc1nsnc1N1CCOCC1
Roles Classification
Biological Role(s): beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
Application(s): antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
antiglaucoma drug
Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
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ChEBI Ontology
Outgoing (S)-timolol (anhydrous) (CHEBI:9599) has role β-adrenergic antagonist (CHEBI:35530)
(S)-timolol (anhydrous) (CHEBI:9599) has role anti-arrhythmia drug (CHEBI:38070)
(S)-timolol (anhydrous) (CHEBI:9599) has role antiglaucoma drug (CHEBI:39456)
(S)-timolol (anhydrous) (CHEBI:9599) has role antihypertensive agent (CHEBI:35674)
(S)-timolol (anhydrous) (CHEBI:9599) is a timolol (CHEBI:39465)
(S)-timolol (anhydrous) (CHEBI:9599) is enantiomer of (R)-timolol (CHEBI:39466)
Incoming (S)-timolol hemihydrate (CHEBI:60787) has part (S)-timolol (anhydrous) (CHEBI:9599)
(S)-timolol maleate (CHEBI:9600) has part (S)-timolol (anhydrous) (CHEBI:9599)
(R)-timolol (CHEBI:39466) is enantiomer of (S)-timolol (anhydrous) (CHEBI:9599)
IUPAC Name
(2S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
Synonyms Sources
(−)-3-morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole ChemIDplus
(2S)-1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-2-propanol ChemIDplus
(S)-1-(1,1-(dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-2-propanol ChemIDplus
(S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol ChemIDplus
(S)-1-tert-Butylamino-3-(4-morpholin-4-yl-[1,2,5]thiadiazol-3-yloxy)-propan-2-ol ChEMBL
(S)-timolol ChEBI
1-(tert-butylamino)-3-[4-(1,4-oxazinan-4-yl)-1,2,5-thiadiazol-3-yloxy]-(2S)-propan-2-ol ChEMBL
S-(−)-3-(3-tert-butylamino-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazole ChemIDplus
Timolol KEGG COMPOUND
Manual Xrefs Databases
4061 DrugCentral
C07141 KEGG COMPOUND
D08600 KEGG DRUG
DB00373 DrugBank
DE1925956 Patent
DE2915955 Patent
LSM-2176 LINCS
TIM PDBeChem
Timolol Wikipedia
US3655663 Patent
US3657237 Patent
View more database links
Registry Numbers Types Sources
1084707 Reaxys Registry Number Reaxys
1084707 Beilstein Registry Number Beilstein
26839-75-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10891117 PubMed citation ChEMBL
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Last Modified
22 February 2017