ChemicalBook > CAS DataBase List > (S)-Timolol maleate

(S)-Timolol maleate

Product Name
(S)-Timolol maleate
CAS No.
26921-17-5
Chemical Name
(S)-Timolol maleate
Synonyms
TIMOLOL MALEATE;Timolol maleate CRS;TimoL;timoptic;2-Propanol, 1-(1,1-dimethylethyl)amino-3-4-(4-morpholinyl)-1,2,5-thiadiazol-3-yloxy-, (2S)-, (2Z)-2-butenedioate (1:1) (salt);mk950;Betim;betime;Tenopt;WP 934
CBNumber
CB3711352
Molecular Formula
C17H28N4O7S
Formula Weight
432.49
MOL File
26921-17-5.mol
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(S)-Timolol maleate Property

Melting point:
202-203 °C(lit.)
alpha 
24405 -12.0° (c = 5 in 1N HCl); D25 -4.2°
storage temp. 
2-8°C
solubility 
H2O: soluble
form 
powder
color 
white to off-white
optical activity
[α]25/D -5.4°, c = 4.9 in 1 M HCl(lit.)
Merck 
14,9444
InChIKey
WLRMANUAADYWEA-NWASOUNVSA-N
CAS DataBase Reference
26921-17-5(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-63-36/37/38
Safety Statements 
36-37/39-26
WGK Germany 
3
RTECS 
UA8475000
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T6394
Product name
Timolol maleate salt
Purity
≥98% (TLC), powder
Packaging
1g
Price
$535
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2593
Product name
Timolol Maleate
Packaging
500MG
Price
$213
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1046
Product name
Timolol maleate
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
500MG
Price
$223
Updated
2024/03/01
Sigma-Aldrich
Product number
1667406
Product name
Timolol maleate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Cayman Chemical
Product number
13974
Product name
Timolol (maleate)
Purity
≥95%
Packaging
25mg
Price
$32
Updated
2024/03/01
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(S)-Timolol maleate Chemical Properties,Usage,Production

Description

Timolol is a non-selective β-adrenergic receptor antagonist with log Kd values of -8.27, -9.86, and -6.8 for binding to human β1-, β2-, and β3-adrenoceptors, respectively. It has been reported that only the (S) enantiomer contributes to the β-blocking effects of racemic timolol, but the weakly active (R) isomer maintains a beneficial effect on intraocular pressure without the undesirable side-effect of bronchial constriction caused by non-selective action of (S)-timolol on β1 and β2 receptors. Timolol has been use alone and in fixed combinations with either prostaglandin analogs or carbonic anhydrase inhibitors to reduce intraocular pressure in research models of ocular hypertension and glaucoma.

Chemical Properties

White Solid

Originator

Blocadren,MSD,UK,1974

Uses

betaadrenergic blocker

Uses

Antihypertensive; antiarrhythmic (class II); antianginal; antiglaucoma agent.

Uses

Anti hypertensive, Anti-glaucoma

Definition

ChEBI: The maleic acid salt of the active (S)-enantiomer of timolol, comprising equimolar amounts of (S)-timolol and maleic acid.

Manufacturing Process

Step A: Preparation of 3-tert-Butylamino-2-Oxopropanol - To an aqueous solution of tert-butylamine (1 mol) at ambient temperature, there is added slowly and with vigorous stirring 2 mols bromoacetol. The reaction mixture is allowed to stand at ambient temperature for about 5 hours whereupon it is made basic by the addition of sodium hydroxide.
The reaction mixture then is extracted with ether, the excess amine is removed from the ethereal solution under reduced pressure and the ether then removed by evaporation to give 3-tert-butylamino-2-oxopropanol. Step B: A solution of the 3-tert-butylamino-2-oxopropanol in a mixture of pyridine hydrochloride and pyridine is treated with p-toluenesulfonylchloride. The mixture is stirred for 1/2 hour at 25° to 30°C and then poured into cold water. The solution is treated with potassium carbonate and the pyridine evaporated in vacuo at a temperature between 55° and 60°C. The aqueous residue is treated with potassium carbonate and the mixture extracted with methylene chloride. Evaporation of the dried extract provides 1- toluenesulfonyloxy-2-oxo-3-tert-butylaminopropane.
Step C: Preparation of 3-Morpholino-4-(3-tert-Butylamino-2-Oxopropoxy)- 1,2,5-Thiadiazole - The 1-toluenesulfonyloxy-2-oxo-3-tert-butylaminopropane, prepared as described in Step B, (11 mols) is added to 0.80 N methanolic sodium methoxide (15 ml) at 0°C. The mixture is stirred for 15 minutes at 0° to 5°C, treated with 3-morpholino-4-hydroxy-1,2,5-thiadiazole (4.29 grams) and then refluxed for 16 hours. The solvent is evaporated in vacuo and the residue is treated with excess potassium carbonate to provide 3-morpholino- 4-(3-butylamino-2-oxopropoxy)-1,2,5-thiadiazole.
Step D: Chemical Reduction Preparation of 3-Morpholino-4-(3-tert_x0002_Butylamino-2-Hydroxypropoxy)-1,2,5-Thiadiazole - The 3-morpholino-4-(3- tert-butylamino-2-oxopropoxy)-1,2,5-thiadiazole (0.01 mol) is dissolved in isopropanol (10 ml). To the solution is added sodium borohydride in portions until the initial evolution of heat and gas subsides. The excess sodium borohydride is destroyed by addition of concentrated hydrochloric acid until the mixture remains acidic. The precipitate of sodium chloride is removed, ether is added, and the solution is concentrated to crystallization. The solid material is removed by filtration and dried thus providing 3-morpholino-4-(3- tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole, MP 161° to 163°C (as hydrochloride).
Alternative Step D: Reduction with a Reductate - Sucrose (1 kg) is dissolved in water (9 liters) in a 20-liter bottle equipped with a gas trap. Baker's yeast (Saccharomyces cerevisiae, 1 kg) is made into a paste with water (1 liter) and added to the sucrose solution with stirring. After lively evolution of gas begins (within 1 to 3 hours), 3-morpholino-4-(3-tert-butylamino-2-oxopropoxy)- 1,2,5-thiadiazole hydrogen maleate [1.35 mols, prepared by reaction of the 3- morpholino-4-(3-tert-butylamino-2-oxopropoxy)-1,2,5-thiadiazole with an equimolar quantity of maleic acid in tetrahydrofuran]. The mixture is allowed to stand until fermentation subsides, after which the bottle is kept in a 32°C incubator until all fermentation has ended (in approximately 1 to 3 days). The yeast is filtered off with addition of diatomaceous earth and the filtrate is evaporated to dryness to give S-3-morpholino-4β-tert-butylamino-2- hydroxypropoxy)-1,2,5-thiadiazole, MP 195° to 198°C (as hydrogen maleate), according to US Patent 3,619,370.
Step E: The base may be converted to the maleate by maleic acid

Therapeutic Function

Antiarrhythmic, Antiglaucoma

Biological Activity

β 1 -adrenergic blocker.

Clinical Use

Beta-adrenoceptor blocker:
Hypertension
Angina
Glaucoma
Migraine prophylaxis

Veterinary Drugs and Treatments

Timolol maleate is used primarily to prevent the development of primary glaucoma in the contralateral eye of a dog which has developed primary glaucoma in one eye. It only reduces intraocular pressure 3 – 10 mmHg and, therefore is of minimal usefulness in patients requiring treatment of primary acute congestive glaucoma. Timolol’s mechanism of action: decreases cyclic-AMP synthesis in non-pigmented ciliary epithelium resulting in decreased aqueous humor production. It may also cause slight miosis in dogs and cats. Timolol maleate is rarely used alone but is combined with dorzolamide solution (Cosopt?). Caution is advised with use of Beta blocking agents in cats with concurrent asthma. As timolol maleate is now available in generic form, it is the primary Beta blocker agent now used.

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: NSAIDs antagonise hypotensive effect.
Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; increased risk of myocardial depression and bradycardia with flecainide.
Antidepressants: enhanced hypotensive effect with MAOIs.
Antihypertensives: enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin.
Antimalarials: increased risk of bradycardia with mefloquine.
Antipsychotics: enhanced hypotensive effect with phenothiazines.
Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil.
Cytotoxics: possible increased risk of bradycardia with crizotinib.
Diuretics: enhanced hypotensive effect.
Fingolimod: possibly increased risk of bradycardia.
Moxisylyte: possible severe postural hypotension.
Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine; also response to adrenaline may be reduced.

Metabolism

Timolol undergoes significant hepatic metabolism, but first pass metabolism is low. The metabolites are excreted in the urine with some unchanged timolol.

(S)-Timolol maleate Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-Timolol maleate Suppliers

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View Lastest Price from (S)-Timolol maleate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Timolol maleate 26921-17-5
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98%-102% USP
Supply Ability
50kgs
Release date
2021-09-29
Baoji Guokang Healthchem co.,ltd
Product
(S)-Timolol maleate 26921-17-5
Price
US $206.30-1439.20/KG
Min. Order
100g
Purity
99%
Supply Ability
800kg
Release date
2021-06-03
Hebei Zhanyao Biotechnology Co. Ltd
Product
(S)-Timolol maleate 26921-17-5
Price
US $10.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
20 Tons
Release date
2021-11-11

26921-17-5, (S)-Timolol maleateRelated Search:


  • 2-Propanol, 1-(1,1-dimethylethyl)amino-3-4-(4-morpholinyl)-1,2,5-thiadiazol-3-yloxy-, (2S)-, (2Z)-2-butenedioate (1:1) (salt)
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  • Timolol maleateQ: What is Timolol maleate Q: What is the CAS Number of Timolol maleate Q: What is the storage condition of Timolol maleate Q: What are the applications of Timolol maleate