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(S)-Timolol maleate

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Name

(S)-Timolol maleate

EINECS 248-111-5
CAS No. 26921-17-5 Density N/A
PSA 182.58000 LogP 0.67020
Solubility N/A Melting Point 202-203 °C(lit.)
Formula C13H24N4O3S.C4H4O4 Boiling Point 487.2 °C at 760 mmHg
Molecular Weight 432.498 Flash Point 248.5 °C
Transport Information N/A Appearance N/A
Safety 26-36/37/39 Risk Codes 22-63
Molecular Structure Molecular Structure of 26921-17-5 ((S)-Timolol maleate) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Istalol;MK 950;Timololum [INN-Latin];Timacor;Timoptol;Optimol;(S)-1-(tert-Butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol;2-Propanol, 1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-, (2S)-;Betime;Blocadren;Timoptic (TN);(2S)-1-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]-3-(tert-butylamino)propan-2-ol;

Article Data 3

(S)-Timolol maleate Synthetic route

26839-75-8

timolol

110-16-7

maleic acid

26921-17-5

timolol maleate

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 1h;
In tetrahydrofuran
26839-75-8

timolol

110-16-7

maleic acid

A

26921-17-5

timolol maleate

B

timolol maleate

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 1h; Title compound not separated from byproducts;

(S)-Timolol maleate Specification

The (S)-Timolol maleate, with the CAS registry number 26921-17-5, has the IUPAC name of (Z)-but-2-enedioic acid;(2S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol. Being a kind of white to off-white powder, it is usually used as the β1-adrenergic blocker, with the product categories including Active Pharmaceutical Ingredients; Adrenoceptor.It is 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.

The physical properties of (S)-Timolol maleate are as follows:
(1)ACD/LogP: 0.20; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.72; (4)ACD/LogD (pH 7.4): -1.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 88.19; (13)Flash Point: 248.5 °C; (14)Enthalpy of Vaporization: 79.32 kJ/mol; (15)Boiling Point: 487.2 °C at 760 mmHg; (16)Vapour Pressure: 2.62E-10 mmHg at 25°C; (17)Exact Mass: 432.16787; (18)MonoIsotopic Mass: 432.16787; (19)Topological Polar Surface Area: 183; (20)Heavy Atom Count: 29; (21)Complexity: 429.

Safety information of (S)-Timolol maleate:
When you are dealing with this chemical, you should be much more cautious. For one thing, it is irritant to eyes, respiratory system and skin, which may also cause inflammation to the skin or other mucous membranes. For another thing, it is harmful which may cause damage to health and it may have possible risk of harm to the unborn child. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(C)(C)NCC(COC1=NSN=C1N2CCOCC2)O.C(=CC(=O)O)C(=O)O
(2)Isomeric SMILES: CC(C)(C)NC[C@@H](COC1=NSN=C1N2CCOCC2)O.C(=C\C(=O)O)\C(=O)O
(3)InChI: 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
(4)InChIKey: WLRMANUAADYWEA-NWASOUNVSA-N 

Below are the toxicity information of (S)-Timolol maleate:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo ocular 39mg/kg/87W-I (39mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Archives of Internal Medicine. Vol. 143, Pg. 1627, 1983.
 
mouse LD50 intraperitoneal 300mg/kg (300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Yakkyoku. Pharmacy. Vol. 32, Pg. 1393, 1981.
mouse LD50 oral 1137mg/kg (1137mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1204, 1981.
mouse LD50 subcutaneous 805mg/kg (805mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1204, 1981.
rat LD50 intraperitoneal 381mg/kg (381mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakkyoku. Pharmacy. Vol. 32, Pg. 1393, 1981.
rat LD50 oral 1028mg/kg (1028mg/kg)   Drugs in Japan Vol. 6, Pg. 464, 1982.
rat LD50 subcutaneous 881mg/kg (881mg/kg)   Drugs in Japan Vol. 6, Pg. 464, 1982.
women LDLo ocular 5ug/kg (0.005mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI
Journal of Family Practice. Vol. 32, Pg. 97, 1991.

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