Timolol

HCID 33624CAS 26839-75-8

Grundinformationen

Standard-SMILES
CC(C)(C)NC[C@H](O)COc1nsnc1N1CCOCC1
InChIKey
BLJRIMJGRPQVNF-JTQLQIEISA-N
Summenformel
C13H24N4O3S
Durchschnittliche Molmasse
316,42 g/mol
Monoisotopische Masse
316,15691163

Überblick

(S)-timolol (anhydrous) is 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. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, an anti-arrhythmia drug and an antiglaucoma drug. It is a conjugate base of a (S)-timolol(1+). It is an enantiomer of a (R)-timolol.

Namen und Bezeichner

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

Namen und Synonyme

timolol26839-75-8BetimolTimololumTimolol anhydrous(-)-3-Morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazoleS-(-)-3-(3-tert-Butylamino-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazole(S)-1-(1,1-(Dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-2-propanol5JKY92S7BR(S)-1-(tert-Butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-olCHEBI:9599Betim
Weitere Namen anzeigen
CHEBI:60787817W3C6175CHEBI:39465TimololoNyogelTiopexGlau-opt2-Propanol, 1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-, hemihydrate, (S)-

Datenbank-Bezeichner

CAS
26839-75-8
PubChem CID
33624
DTXSID
DTXSID4023674
ChEMBL
CHEMBL499
ChEBI
CHEBI:9599
UNII
5JKY92S7BR
EC Number
248-032-6
Nikkaji
J10.426D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,8
Polarare Oberfläche (TPSA)
108 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
7
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Solubilitysoluble in water
Human Drugs · 5 Einträge

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics; Antiglaucoma Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Ophthalmological preparations > Miotics and antiglaucoma medicines

Boiling Point>100
Melting Point · 2 Einträge

202-203

71.5-72.5 °C

Stability/Shelf Life · 2 Einträge

Solutions of timolol maleate are stable up to a pH of 12. In general, timolol ophthalmic solutions should be protected from light and stored in tight containers at 15-30 °C and protected from freezing. ... Timolol gel-forming ophthalmic solution should be stored at 15-25 °C. /Timolol Maleate/

Timolol maleate tablets should be stored in well closed, light resistant containers at a temperature less than 40 °C, preferably between 15-30 °C. /Timolol maleate/

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P263, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 24-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34327
Other Safety InformationIMAP assessments - 2-Propanol, 1-[(1,1-dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-, (S)-: Environment tier I assessment
FDA Requirements · 2 Einträge

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl timolol and timolol maleate, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /Timolol and timolol maleate/

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Special Reports · 2 Einträge

Fraunfelder FT; Ocular Beta-blockers and Systemic Effects. Arch Intern Med 146 (Jun): 1073-74 (1986). The physiological and metabolic systems which contribute to the systemic side effects of timolol maleate when given as ophthalmic drops were described and discussed. The specific reactions ascribed to this medication were also listed. /Timolol maleate/

Jackson CD, Fishbein L; A Toxicological Review of Beta-adrenergic Blockers. Fundam Appl Toxicol 6 (3): 395-422 (1986). The use of various beta-adrenergic blockers has become extensive as they have been found to be efficacious in the treatment of a number of cardiovascular problems including cardiac arrhythmias, angina pectoris, and hypertension. The widespread and chronic use of these drugs has generated a concern for their potential chronic toxicity. Eighteen beta-adrenergic blockers have been reviewed and the available literature pertaining to their potential carcinogenicity, mutagenicity, and teratogenicity has been summarized and compared.

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Toxikologische Informationen

Body BurdenTimolol is distributed into milk.
Interactions · 5 Einträge

When used in conjunction with topical miotics, topical dipivefrin, topical epinephrine, and/or systemically administered carbonic anhydrase inhibitors, the effect of timolol maleate in lowering intraocular pressure may be additive. This effect may be used to therapeutic advantage in the treatment of glaucoma. However, the long term efficacy of combined therapy with an adrenergic agonist (eg, dipivefrin, epinephrine) and a beta-adrenergic blocking agent remains to be clearly established. Although topical timolol used alone has little or no effect on pupil size, mydriasis resulting from concomitant therapy with topical timolol and epinephrine has been reported occasionally. /Timolol maleate/

The possibility of an additive effect on intraocular pressure and/or systemic beta-adrenergic blockade should be considered in patients who are receiving a systemic beta-adrenergic blocking agent and topical timolol concomitantly.

When topical timolol is administered concomitantly with a catecholamine depleting drug (eg, reserpine), the patient should be observed closely for possible additive effects and the production of hypotension and/or marked bradycardia, which may result in vertigo, syncope, and or postural hypotension.

Concomitant administration of timolol with reserpine may increase the incidence of hypotension and bradycardia as compared with timolol alone, because of reserpine's catecholamine depleting activity. Timolol also is additive with and may potentiate the hypotensive actions of other hypotensive agents (e.g., hydralazine, methyldopa). This effect usually is used to therapeutic advantage, but dosage should be adjusted carefully when these drugs are used concurrently.

For more Interactions (Complete) data for TIMOLOL (8 total), please visit the HSDB record page.

Hepatotoxicity · 1 Eintrag

Mild-to-moderate elevations in serum aminotransferase levels occur in less than 2% of patients on timolol and are usually transient and asymptomatic, resolving even with continuation of therapy. Despite its wide spread use, timolol has not been convincingly linked to instances of clinically apparent liver injury. Other beta-blockers have been implicated in rare instances of acute liver injury with a latency to onset ranging from 2 to 24 weeks, a hepatocellular pattern of serum enzyme elevations and a mild, self-limiting course without evidence of hypersensitivity or autoimmune reactions.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that timolol is expected to have moderate mobility in soil(SRC). Volatilization of timolol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-17 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Timolol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-8 mm Hg(SRC), determined from a fragment constant method(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that timolol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.3X10-17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), timolol, which has an estimated vapor pressure of 1.4X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase timolol may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsTimolol administration is associated with various adverse reactions, depending on the administration method and ocular and systemic exposure level. The most common adverse reactions are listed below.
Milk ConcentrationsTimolol is distributed into milk.

Regulatorische Informationen

FDA Requirements · 2 Einträge

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl timolol and timolol maleate, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /Timolol and timolol maleate/

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 6 Einträge

S01ED01

C - Cardiovascular system

S - Sensory organs

QC - Cardiovascular system

QS - Sensory organs

S01ED01

Protein BindingThe plasma protein binding of timolol is not extensive and is estimated to be about 10%.
Pharmacodynamics · 1 Eintrag

Timolol, when administered by the ophthalmic route, rapidly reduces intraocular pressure. When administered in the tablet form, it reduces blood pressure, heart rate, and cardiac output, and decreases sympathetic activity.. This drug has a fast onset of action, usually occurring within 20 minutes of the administration of an ophthalmic dose. Timolol maleate can exert pharmacological actions for as long as 24 hours if given in the 0.5% or 0.25% doses.

Mechanism of Action · 4 Einträge

Timolol competes with adrenergic neurotransmitters for binding to beta(1)-adrenergic receptors in the heart and the beta(2)-receptors in the vascular and bronchial smooth muscle. This leads to diminished actions of catecholamines, which normally bind to adrenergic receptors and exert sympathetic effects leading to an increase in blood pressure and heart rate. Beta(1)-receptor blockade by timolol leads to a decrease in both heart rate and cardiac output during rest and exercise, and a decrease in both systolic and diastolic blood pressure. In addition to this, a reduction in reflex orthostatic hypotension may also occur. The blockade of beta(2) receptors by timolol in the blood vessels leads to a decrease in peripheral vascular resistance, reducing blood pressure. The exact mechanism by which timolol reduces ocular pressure is unknown at this time, however, it likely decreases the secretion of aqueous humor in the eye. According to one study, the reduction of aqueous humor secretion may occur through the decreased blood supply to the ciliary body resulting from interference with the active transport system or interference with prostaglandin biosynthesis.

beta-Adrenergic blocker

Following topical application to the eye, timolol maleate reduces both elevated and normal intraocular pressure in patients with or without open angle (chronic simple, noncongestive) glaucoma or ocular hypertension. Timolol reduces intraocular pressure with little or no effect on accommodation or pupillary size. In patients with elevated intraocular pressure, timolol reduces mean intraocular pressure by about 25-33%. The drug appears to be equally effective in light and dark colored eyes. ... The exact mechanism by which beta-blockers, including timolol, reduce intraocular pressure has not been clearly defined. Fluorophotometric studies suggest that reduced aqueous humor formation is the predominant effect. beta-Adrenergic blocking agents may block endogenous catecholamine stimulated increases in cyclic adenosine monophosphate concentrations within the ciliary processes and subsequent formation of aqueous humor. Timolol appears to cause little or no change in aqueous humor outflow facility. ... In some studies, timolol maleate applied topically to one eye reduced intraocular pressure in both eyes; the mechanism of this effect has not been elucidated. ... A slight decrease in the intraocular hypotensive effect may occur during the first 3 wk of timolol therapy, and tolerance may develop with prolonged use; however, the intraocular pressure lowering effect has been maintained for at least 3 yr with continuous use of the drug in some patients. /Timolol maleate/

Timolol maleate has pharmacologic actions similar to those of other beta-adrenergic blocking agents. The principal physiologic action of timolol is to competitively block beta-adrenergic receptors within the myocardium (beta1-receptors) and within bronchial and vascular smooth muscle (beta2-receptors). Unlike atenolol and metoprolol, timolol is not a beta1-selective adrenergic blocking agent; timolol is a nonselective beta-adrenergic blocking agent, inhibiting both beta1- and beta2-adrenergic receptors. Timolol also does not exhibit the intrinsic sympathomimetic activity seen with pindolol or the membrane stabilizing activity possessed by propranolol or pindolol. ... By inhibiting myocardial beta1-adrenergic receptors, timolol produces negative chronotropic and inotropic activity. The negative chronotropic action of timolol on the sinoatrial node results in a decrease in the rate of sinoatrial node discharge and an increase in recovery time, thereby decreasing resting and exercise stimulated heart rate and reflex orthostatic tachycardia by as much as 30%. High doses of the drug may produce sinus arrest, especially in patients with SA node disease (eg, sick sinus syndrome). Timolol also slows conduction in the atrioventricular node. Timolol usually produces a slight reduction in cardiac output, probably secondary to its effect on heart rate. The decrease in myocardial contractility and heart rate produced by timolol leads to a reduction in myocardial oxygen consumption which accounts for the effectiveness of the drug in chronic stable angina pectoris. ... Timolol suppresses plasma renin activity and suppresses the renin aldosterone-angiotensin system. The renin lowering effect of beta-adrenergic blocking agents may lead to a minimal reduction in glomerular filtration rate and occasionally may reduce renal blood flow; however, other mechanisms (eg, decreased cardiac output, unopposed alpha-mediated renal vasoconstriction) also probably contribute to these effects. Because of the suppression of aldosterone production, beta-adrenergic blocking agents usually produce no measurable increases in plasma volume or sodium and water retention. ... The precise mechanism of timolol's hypotensive effect has not been determined. Timolol may transiently increase peripheral vascular resistance at rest and with exercise, but peripheral vascular resistance usually returns to baseline with continued administration of the drug. It has been postulated that beta-adrenergic blocking agents reduce blood pressure by blocking peripheral (especially cardiac) adrenergic receptors (decreasing cardiac output), by decreasing sympathetic outflow from the CNS, and/or by suppressing renin release. /Timolol maleate/

Biological Half-Life · 2 Einträge

Timolol half-life was measured at 2.9 ± 0.3 h hours in a clinical study of healthy volunteers.

Plasma half-life 3-5 hr

Metabolism/Metabolites · 4 Einträge

Timolol is metabolized in the liver by the cytochrome P450 2D6 enzyme, with minor contributions from CYP2C19. 15-20% of a dose undergoes first-pass metabolism. Despite its relatively low first pass metabolism, timolol is 90% metabolized. Four metabolites of timolol have been identified, with a hydroxy metabolite being the most predominant.

It is metabolized extensively by the liver, and only a small amount of unchanged drug appears in the urine.

The metabolism of timolol maleate to its ring cleavage ethanolamine and glycine products was studied in 108 patients with essential hypertension who received 10 mg oftimolol maleate, administered as a single oral dose. The metabolism of timolol maleate was determined to be partly under monogenic control of the debrisoquine-type. The mean plasmatimolol maleate concentration in poor metabolizers of debrisoquine were double that of extensiv metabolizers. /Timolol maleate/

Timolol has known human metabolites that include 4-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,5-thiadiazol-3-yl]morpholin-2-ol.

Verwendung und Herstellung

Uses · 2 Einträge

MEDICATION

Use (kg; approx.) in Germany (2009): >250

Formulations/Preparations · 5 Einträge

Tablets, 5, 10, and 20 mg. Ophthalmic solution, 0.25% and 0.5%. /Timolol maleate/

Ophthalmic Solution, 0.25% (of timolol), Timoptic (with benzalkonium chloride), Merck; Timoptic in Ocudose (preservative-free), Merck; 0.5% (of timolol), Timoptic (with benzalkonium chloride), Merck; Timoptic in Ocudose (preservative- free), Merck. /Timolol maleate/

Oral Tablets, 5 mg Biocardren, Merck; 10 mg, Biocardren (scored), Merck; 20 mg, Biocardren (scored), Merck. /Timolol maleate/

Oral Tablets, 10 mg with Hydrochlorothiazide 25, Timolide, Merck. /Timolol maleate combinations/

For more Formulations/Preparations (Complete) data for TIMOLOL (6 total), please visit the HSDB record page.

Use ClassificationPharmaceuticals
General Manufacturing Information2-Propanol, 1-[(1,1-dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-, (2S)-: INACTIVE

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