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

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

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

Supplier Information	ChemicalBook:CB3266706, eMolecules:1933616, ZINC000000002176

Download	Molfile XML SDF

more structures >>

Wikipedia	License
Timolol is a beta blocker medication used either by mouth or as eye drops. As eye drops it is used to treat increased pressure inside the eye such as in ocular hypertension and glaucoma. By mouth it is used for high blood pressure, chest pain due to insufficient blood flow to the heart, to prevent further complications after a heart attack, and to prevent migraines. Common side effects with the drops is irritation of the eye. Common side effects by mouth include tiredness, slow heart beat, itchiness, and shortness of breath. Other side effects include masking the symptoms of low blood sugar in those with diabetes. Use is not recommended in those with asthma, uncompensated heart failure, or chronic obstructive pulmonary disease (COPD). It is unclear if use during pregnancy is safe for the fetus. Timolol is a non-selective beta blocker. Timolol was patented in 1968, and came into medical use in 1978. It is on the World Health Organization's List of Essential Medicines. Timolol is available as a generic medication. In 2022, it was the 155th most commonly prescribed medication in the United States, with more than 3 million prescriptions.
Read full article at Wikipedia

Formula

C13H24N4O3S

Net Charge

Average Mass

316.42000

Monoisotopic Mass

316.15691

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.

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 conjugate base of (S)-timolol(1+) (CHEBI:188157) (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) (S)-timolol(1+) (CHEBI:188157) is conjugate acid of (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

Citations

Last Modified

22 February 2017