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Merck

T6394

Timolol maleate salt

≥98% (TLC), β-adrenoceptor antagonist, powder

Synonym(s):

S-(−)-1-(t-Butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]-2-propanol maleate salt, Timolol hydrogen maleate

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About This Item

Empirical Formula (Hill Notation):
C13H24N4O3S · C4H4O4
CAS Number:
26921-17-5
Molecular Weight:
432.49
NACRES:
NA.77
PubChem Substance ID:
24277810
UNSPSC Code:
12352200
EC Number:
248-111-5
MDL number:
MFCD00058356
Assay:
≥98% (TLC)
Form:
powder
Quality level:
200

Key Documents

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Product Name

Timolol maleate salt, ≥98% (TLC), powder

InChI key

WLRMANUAADYWEA-NWASOUNVSA-N

InChI

1S/C13H24N4O3S.C4H4O4/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17;5-3(6)1-2-4(7)8/h10,14,18H,4-9H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t10-;/m0./s1

SMILES string

[H]\C(=C(/[H])C(O)=O)C(O)=O.CC(C)(C)NC[C@H](O)COc1nsnc1N2CCOCC2

assay

≥98% (TLC)

form

powder

optical activity

[α]25/D -5.4°, c = 4.9 in 1 M HCl(lit.)

color

white to off-white

mp

202-203 °C (lit.)

solubility

H2O: soluble, ethanol: soluble

ε (extinction coefficient)

8,700 at 294 nm at 1 M

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

Quality Level

200

Gene Information

human ... ADRB1(153), ADRB2(154), ADRB3(155)

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Application

Timolol maleate has been used as an adrenergic β-blocker for evaluating cardiovascular functions in mice5. It has also been used for evaluating the uptake of 86Rb+ in rat cardiomyocytes6.

Biochem/physiol Actions

Timolol maleate is a class II anti-arrhythmic agent that functions as a non-selective β-adrenoceptor antagonist, a vasodilator and an anti-glaucoma agent. Studies have reported that timolol maleate can be used for the treatment of infantile hemangioma (IH)7.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Timolol maleate is soluble in ethanol and water.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

hcodes

H302,H361

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SLBC3834V
073H0074
061K1290
045H1255
045H1254

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Verena Prokosch et al.
PloS one, 8(2), e49730-e49730 (2013-03-08)
Optic nerve atrophy caused by abnormal intraocular pressure (IOP) remains the most common cause of irreversible loss of vision worldwide. The aim of this study was to determine whether topically applied IOP-lowering eye drugs affect retinal ganglion cells (RGCs) and
G C Chiou et al.
Journal of ocular pharmacology, 8(3), 183-190 (1992-01-01)
An ocular hypertensive rabbit eye model was used to study the effect of L- and D-timolol on retinal and choroidal blood flow. Ocular hypertension was induced artificially by raising the intraocular pressure to 40 mmHg which reduced the ocular blood
Ajith Chakkittakandiyil et al.
Pediatric dermatology, 29(1), 28-31 (2011-12-14)
Therapeutic options for superficial infantile hemangiomas (IH) are limited. Recently, timolol maleate gel, a topical nonselective beta-blocker, has been reported as a potentially effective treatment for superficial IH. This study is an extension of a previously published pilot study designed
Hyun Jung Jung et al.
Journal of controlled release : official journal of the Controlled Release Society, 165(1), 82-89 (2012-11-06)
Glaucoma is the second major cause of blindness in the world after cataract. Glaucoma management through eye drops that reduce the intraocular pressure (IOP) has major deficiencies including low patient compliance and low bioavailability. Extended wear contact lenses that deliver
M Gallarate et al.
International journal of pharmaceutics, 440(2), 126-134 (2012-10-20)
After an initial screening of ingredients and production methods, nanoemulsions for ocular administration of timolol containing the drug as maleate (TM) or as ion-pair with AOT (TM/AOT) were prepared. The physico-chemical characterization of nanoemulsions, regarding mean diameter, pH, zeta potential
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