QuickView for Timolol (compound)

Summary
General Info

PubChem

PubChem Compound 33624

Name:	Timolol
PubChem Compound ID:	33624
Description:	A beta-adrenergic antagonist similar in action to PROPRANOLOL. The levo-isomer is the more active. Timolol has been proposed as an antihypertensive, antiarrhythmic, antiangina, and antiglaucoma agent. It is also used in the treatment of MIGRAINE DISORDERS and tremor.
Molecular formula:	C₁₃H₂₄N₄O₃S
Molecular weight:	316.421 g/mol
Synonyms:	Lopac-T-6394; NCGC00016798-01; Istalol; SPBio_003075; 194288-09-0; Prestwick0_000948; (S)-1-(1,1-(Dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-2-propanol; Prestwick1_000948; 2-Propanol, 1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-, (2S)-; 26921-17-5. show more » Lopac-T-6394; NCGC00016798-01; Istalol; SPBio_003075; 194288-09-0; Prestwick0_000948; (S)-1-(1,1-(Dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-2-propanol; Prestwick1_000948; 2-Propanol, 1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-, (2S)-; 26921-17-5; (-)-3-Morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole; Timololum [INN-Latin]; (S)-1-(tert-Butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol; EINECS 248-032-6; Timolol; 131628-37-0; Tocris-0649; Timopic; 26839-75-8; NCGC00022033-02; S-(-)-3-(3-tert-Butylamino-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazole; NCGC00016038-01; CAS-26921-17-5; HSDB 6533; C07141; Blocadren show less «

DrugBank

Identification

Name:	Timolol
Name (isomeric):	DB00373
Drug Type:	small molecule
Description:	A beta-adrenergic antagonist similar in action to PROPRANOLOL. The levo-isomer is the more active. Timolol has been proposed as an antihypertensive, antiarrhythmic, antiangina, and antiglaucoma agent. It is also used in the treatment of MIGRAINE DISORDERS and tremor.
Synonyms:	Timololum [INN-Latin]; Timolol maleate
Brand:	Apo-Timop, Timoptic OcuDose, Novo-Timol, Timoptol, Apo-Timol, Timoptic-XE, Timopic, Tim-AK, Nu-Timolol, Blocadren, Timoptic, Betimol, Tenopt, Temserin, Timacor, Timacar, Aquanil, Betim, Istalol, Phoxal-timolol, Timoptic in Ocudose, Proflax
Brand name mixture:	Timpilo 2(Pilocarpine Hydrochloride + Timolol Maleate), Combigan(Brimonidine Tartrate + Timolol Maleate), Xalacom(Latanoprost + Timolol Maleate), Cosopt(Dorzolamide Hydrochloride + Timolol Maleate), Timolide Tab(Hydrochlorothiazide + Timolol Maleate), Timpilo 4(Pilocarpine Hydrochloride + Timolol Maleate)
Category:	Adrenergic beta-Antagonists, Anti-Arrhythmia Agents, Antihypertensive Agents
CAS number:	26839-75-8

Pharmacology

Indication:	In its oral form it is used to treat high blood pressure and prevent heart attacks, and occasionally to prevent migraine headaches. In its opthalmic form it is used to treat open-angle and occasionally secondary glaucoma.
Pharmacology:	Similar to propranolol and nadolol, timolol is a non-selective, beta-adrenergic receptor antagonist. Timolol does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity, but does possess a relatively high degree of lipid solubility. Timolol, when applied topically to the eye... show more » Similar to propranolol and nadolol, timolol is a non-selective, beta-adrenergic receptor antagonist. Timolol does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity, but does possess a relatively high degree of lipid solubility. Timolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage. show less «
Mechanism of Action:	Like propranolol and nadolol, timolol competes with adrenergic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascular smooth muscle and beta(2)-receptors in the bronchial and vascular smooth muscle. Beta(1)-receptor blockade results in a decrease in resting and exercise heart rate and cardiac ... show more » Like propranolol and nadolol, timolol competes with adrenergic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascular smooth muscle and beta(2)-receptors in the bronchial and vascular smooth muscle. Beta(1)-receptor blockade results in a decrease in resting and exercise heart rate and cardiac output, a decrease in both systolic and diastolic blood pressure, and, possibly, a reduction in reflex orthostatic hypotension. Beta(2)-blockade results in an increase in peripheral vascular resistance. The exact mechanism whereby timolol reduces ocular pressure is still not known. The most likely action is by decreasing the secretion of aqueous humor. show less «
Absorption:	Bioavailability is about 60%
Protein binding:	~10%
Biotransformation:	Primarily hepatic (80%) via the cytochrome P450 2D6 isoenzyme.
Route of elimination:	Timolol and its metabolites are primarily excreted in the urine.
Half Life:	2.5-5 hours
Toxicity:	LD₅₀=1190 mg/kg (oral, mice), LD₅₀=900 mg/kg (oral, rat). Symptoms of overdose include drowsiness, vertigo, headache, and atriventricular block.
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Glycodiazine	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Methyldopa	Possible hypertensive crisis
Cimetidine	Cimetidine may increase the serum concentration of timolol by decreasing its metabolism.
Ketoprofen	The NSAID, Ketoprofen, may antagonize the antihypertensive effect of Timolol.
Lidocaine	The beta-blocker, timolol, may increase the effect and toxicity of lidocaine.

Glycodiazine	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Methyldopa	Possible hypertensive crisis
Cimetidine	Cimetidine may increase the serum concentration of timolol by decreasing its metabolism.
Ketoprofen	The NSAID, Ketoprofen, may antagonize the antihypertensive effect of Timolol.
Lidocaine	The beta-blocker, timolol, may increase the effect and toxicity of lidocaine.
Procaterol	Antagonism
Diflunisal	The NSAID, Diflunisal, may antagonize the antihypertensive effect of Timolol.
Diltiazem	Additive effects of decreased heart rate and contractility may occur. Increased risk of heart block.
Ketorolac	The NSAID, Ketorolac, may antagonize the antihypertensive effect of Timolol.
Terbinafine	Terbinafine may reduce the metabolism and clearance of Timolol. Consider alternate therapy or monitor for therapeutic/adverse effects of Amytriptyline if Timolol is initiated, discontinued or dose changed.
Salmeterol	Antagonism
Etodolac	The NSAID, Etodolac, may antagonize the antihypertensive effect of Timolol.
Fenoterol	Antagonism
Chlorpropamide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Pipobroman	Antagonism
Orciprenaline	Antagonism
Insulin Glargine	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Naproxen	The NSAID, Naproxen, may antagonize the antihypertensive effect of Timolol.
Gliclazide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Isoproterenol	Antagonism
Pirbuterol	Antagonism
Repaglinide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Prazosin	Risk of hypotension at the beginning of therapy
Lumiracoxib	The NSAID, Lumiracoxib, may antagonize the antihypertensive effect of Timolol.
Piroxicam	Risk of inhibition of renal prostaglandins
Indomethacin	Risk of inhibition of renal prostaglandins
Verapamil	Additive effects of decreased heart rate and contractility may occur. Increased risk of heart block.
insulin inhaled	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Ergonovine	Ischemia with risk of gangrene
Ergotamine	Ischemia with risk of gangrene
Epinephrine	Hypertension, then bradycardia
Oxtriphylline	Antagonism of action and increased effect of theophylline
Terazosin	Increased risk of hypotension. Initiate concomitant therapy cautiously.
Clonidine	Increased hypertension when clonidine stopped
Tiaprofenic acid	The NSAID, Tiaprofenic acid, may antagonize the antihypertensive effect of Timolol.
Glisoxepide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Oxaprozin	The NSAID, Oxaprozin, may antagonize the antihypertensive effect of Timolol.
Disopyramide	The beta-blocker, timolol, may increase the toxicity of disopyramide.
Meloxicam	The NSAID, Meloxicam, may antagonize the antihypertensive effect of Timolol.
Insulin	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Acetohexamide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Dyphylline	Antagonism of action and increased effect of theophylline
Terbutaline	Antagonism
Celecoxib	The NSAID, Celecoxib, may antagonize the antihypertensive effect of Timolol.
Methysergide	Ischemia with risk of gangrene
Treprostinil	Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Salbutamol	Antagonism
Diclofenac	The NSAID, Diclofenac, may antagonize the antihypertensive effect of Timolol.
Meclofenamic acid	The NSAID, Meclofenamate, may antagonize the antihypertensive effect of Timolol.
Tolmetin	The NSAID, Tolmetin, may antagonize the antihypertensive effect of Timolol.
Formoterol	Antagonism
Dihydroergotamine	Ischemia with risk of gangrene
Dihydroergotoxine	Ischemia with risk of gangrene
Sulindac	The NSAID, Sulindac, may antagonize the antihypertensive effect of Timolol.
Tolbutamide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Tolazamide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Aminophylline	Antagonism of action and increased effect of theophylline
Theophylline	Antagonism of action and increased effect of theophylline
Nabumetone	The NSAID, Nabumetone, may antagonize the antihypertensive effect of Timolol.
Glipizide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Fenoprofen	The NSAID, Fenoprofen, may antagonize the antihypertensive effect of Timolol.
Glyburide	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Flurbiprofen	The NSAID, Flurbiprofen, may antagonize the antihypertensive effect of Timolol.

show less «

Targets

Beta-1 adrenergic receptor

Beta-2 adrenergic receptor

Lysozyme

Enzymes

Cytochrome P450 2D6

Cytochrome P450 2C19

Transporters

Multidrug resistance protein 1