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63659-18-7

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63659-18-7 Usage

Chemical Properties

White Crystalline Solid

Originator

Kerlone,Carriere,France,1983

Uses

Different sources of media describe the Uses of 63659-18-7 differently. You can refer to the following data:
1. Cardioselective 1-adrenergic blocker. An antihypertensive; antiglaucoma
2. Cardioselective β1-adrenergic blocker. An antihypertensive; antiglaucoma.

Definition

ChEBI: A propanolamine that is 3-aminopropane-1,2-diol in which the hydrogen of the primary hydoxy is substituted by a 4-[2-(cyclopropylmethoxy)ethyl]phenyl group and one of the hydrogens attached to the amino group is substituted by isopropyl. It is a selective beta1-receptor blocker and is used in the treatment of glaucoma as well as hypertension, arrhythmias, and coronary heart disease. It is also used to reduce non-fatal cardiac events in patients with heart failure.

Manufacturing Process

(1) 1 g of sodium hydroxide pellets (0.025 mol) is added to a suspension of 3.8 g of 4-[2-(cyclopropylmethoxy)-ethyl]-phenol in 30 ml of water. When the solution becomes homogenous, 2.3 ml of epichlorohydrin are added and the mixture is stirred for 8 hours. It is then extracted with ether and the extract is washed with water, dried over sodium sulfate and evaporated to dryness. The compound is purified by passing it over a silica column. 2.4 g of 1-[4-[2- (cyclopropylmethoxy)ethyl]-phenoxy]-2,3-epoxy-propane are thus obtained. (2) 4.9 g of the preceding compound (0.02 mol) are condensed with 25 ml of isopropylamine by contact for 8 hours at ambient temperature and then by heating for 48 hours at the reflux temperature. After evaporation to dryness, the compound obtained is crystallized from petroleum ether. 5 g (yield 80%) of 2-[[4-(2-cyclopropylmethoxy)-ethyl]-phenoxy]-3-isopropylaminopropan-2-ol are thus obtained, melting point 70° to 72°C. The hydrochloride is prepared by dissolving the base in the minimum amount of acetone and adding a solution of hydrochloric acid in ether until the pH is acid. The hydrochloride which has precipitated is filtered off and is recrystallized twice from acetone, melting point 116°C.

Brand name

Betoptic (Alcon); Kerlone (Sanofi Aventis).

Therapeutic Function

Beta-adrenergic blocker

Biological Activity

betaxolol is a cardioselective beta-adrenergic receptor blocking agent. betaxolol (5 mg/kg via i.p. injection) was administered at 24 and then 44 h following the final chronic cocaine administration. animals treated with betaxolol during cocaine withdrawal

Veterinary Drugs and Treatments

Betaxolol HCl is a specific Beta1 adrenergic blocking agent which reduces aqueous humor production by decreasing cyclic-AMP synthesis in the ciliary body. This drug is a suitable substitute for timolol and because of its specific Beta1 activity, might be a first choice Beta blocking agent for patients with concurrent respiratory disease. Either levobunolol HCl or betaxolol HCl would be the first choice Beta blocking agent in a feline patient with glaucoma and asthma, although a topical carbonic anhydrates inhibitor should be considered before a Beta blocking agent in this situation. Betaxolol and the other Beta blockers should be used with caution in patients with cardiac disease.

Metabolism

Absorption of an oral dose of betaxolol (Kerlone, Betoptic) is almost complete. The drug is subject to a slight first-pass effect such that the absolute bioavailability of the drug is about 90%.Approximately 50% of administered betaxolol binds to plasma proteins, and its plasma half-life is about 20 hours; it is suitable for dosing once per day.The primary route of elimination is by liver metabolism, with only 15% of unchanged drug being excreted.

Check Digit Verification of cas no

The CAS Registry Mumber 63659-18-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,3,6,5 and 9 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 63659-18:
(7*6)+(6*3)+(5*6)+(4*5)+(3*9)+(2*1)+(1*8)=147
147 % 10 = 7
So 63659-18-7 is a valid CAS Registry Number.
InChI:InChI=1/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3

63659-18-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name betaxolol

1.2 Other means of identification

Product number -
Other names Betaxolol [INN:BAN]

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:63659-18-7 SDS

63659-18-7Synthetic route

isopropylamine
75-31-0

isopropylamine

1-[2-(cyclopropyl-methoxy)-ethyl]-4-(2,3-epoxypropoxy)-benzene
63659-17-6

1-[2-(cyclopropyl-methoxy)-ethyl]-4-(2,3-epoxypropoxy)-benzene

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
for 24h; Ambient temperature;90%
for 48h; Heating; Yield given;
In water at 0 - 35℃;
RS 1-{4-[2-(allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-ol
884340-61-8

RS 1-{4-[2-(allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-ol

diiodomethane
75-11-6

diiodomethane

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
With diethylzinc In toluene at 0℃; for 16h;84%
2-Phenyl-3-isopropyl-5-[[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]methyl]oxazolidine

2-Phenyl-3-isopropyl-5-[[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]methyl]oxazolidine

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol74%
4-[2-(cyclopropylmethoxy)-ethyl]-phenol
63659-16-5

4-[2-(cyclopropylmethoxy)-ethyl]-phenol

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / H2O / 12 h / Ambient temperature
2: 48 h / Heating
View Scheme
1-benzyloxy-4-(2-cyclopropylmethoxyethyl)benzene
63659-15-4

1-benzyloxy-4-(2-cyclopropylmethoxyethyl)benzene

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / H2 / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr
2: NaOH / H2O / 12 h / Ambient temperature
3: 48 h / Heating
View Scheme
2-(4-benzyloxyphenyl)ethanol
61439-59-6

2-(4-benzyloxyphenyl)ethanol

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) NaH / 1.) DMF, 2.) DMF, 60 deg, 18 h
2: 84 percent / H2 / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr
3: NaOH / H2O / 12 h / Ambient temperature
4: 48 h / Heating
View Scheme
2-<4-(phenylmethoxy)phenyl>acetic acid ethyl ester
56441-69-1

2-<4-(phenylmethoxy)phenyl>acetic acid ethyl ester

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 86 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature
2: 1.) NaH / 1.) DMF, 2.) DMF, 60 deg, 18 h
3: 84 percent / H2 / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr
4: NaOH / H2O / 12 h / Ambient temperature
5: 48 h / Heating
View Scheme
betaxolol Hydrochloride
63659-19-8

betaxolol Hydrochloride

betaxolol
63659-18-7

betaxolol

Conditions
ConditionsYield
With Dowex Marathon 11 chloride form In water
betaxolol
63659-18-7

betaxolol

acetic anhydride
108-24-7

acetic anhydride

1-(N-acetyl-N-isopropyl)amino-3-<4-(2-cyclopropylmethoxy)ethyl>phenoxyprop-2-yl acetate
169613-96-1

1-(N-acetyl-N-isopropyl)amino-3-<4-(2-cyclopropylmethoxy)ethyl>phenoxyprop-2-yl acetate

Conditions
ConditionsYield
With pyridine for 24h; Ambient temperature;100%
With pyridine; triethylamine at 20℃;
betaxolol
63659-18-7

betaxolol

acetic anhydride
108-24-7

acetic anhydride

A

N-{(R)-3-[4-(2-Cyclopropylmethoxy-ethyl)-phenoxy]-2-hydroxy-propyl}-N-isopropyl-acetamide

N-{(R)-3-[4-(2-Cyclopropylmethoxy-ethyl)-phenoxy]-2-hydroxy-propyl}-N-isopropyl-acetamide

B

Acetic acid (S)-2-(acetyl-isopropyl-amino)-1-[4-(2-cyclopropylmethoxy-ethyl)-phenoxymethyl]-ethyl ester
169613-97-2

Acetic acid (S)-2-(acetyl-isopropyl-amino)-1-[4-(2-cyclopropylmethoxy-ethyl)-phenoxymethyl]-ethyl ester

Conditions
ConditionsYield
With pyridine for 24h; Ambient temperature; Yield given. Yields of byproduct given;
betaxolol
63659-18-7

betaxolol

cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

cyclopropanecarboxylic acid 2-[4-(2-cyclopropylmethoxy-ethyl)-phenoxy]-1-(isopropylamino-methyl)-ethyl ester

cyclopropanecarboxylic acid 2-[4-(2-cyclopropylmethoxy-ethyl)-phenoxy]-1-(isopropylamino-methyl)-ethyl ester

Conditions
ConditionsYield
Acylation;
betaxolol
63659-18-7

betaxolol

betaxolol Hydrochloride
63659-19-8

betaxolol Hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In acetone at 10 - 15℃; pH=2.0;
betaxolol
63659-18-7

betaxolol

(S)-betaxolol hydrochloride

(S)-betaxolol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine; triethylamine / 20 °C
2: Rhodotorula mucilaginosa DQ832198 / 12 h / 28 °C / pH 6 / Microbiological reaction; phosphate-citric acid buffer
3: sodium hydroxide / methanol / 20 °C
4: hydrogenchloride / water / 20 °C
View Scheme
betaxolol
63659-18-7

betaxolol

(-)-Betaxolol
93221-48-8

(-)-Betaxolol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine; triethylamine / 20 °C
2: Rhodotorula mucilaginosa DQ832198 / 12 h / 28 °C / pH 6 / Microbiological reaction; phosphate-citric acid buffer
3: sodium hydroxide / methanol / 20 °C
View Scheme
betaxolol
63659-18-7

betaxolol

Acetic acid (S)-2-(acetyl-isopropyl-amino)-1-[4-(2-cyclopropylmethoxy-ethyl)-phenoxymethyl]-ethyl ester
169613-97-2

Acetic acid (S)-2-(acetyl-isopropyl-amino)-1-[4-(2-cyclopropylmethoxy-ethyl)-phenoxymethyl]-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine; triethylamine / 20 °C
2: Rhodotorula mucilaginosa DQ832198 / 12 h / 28 °C / pH 6 / Microbiological reaction; phosphate-citric acid buffer
View Scheme
betaxolol
63659-18-7

betaxolol

A

(+)-Betaxolol
91878-53-4

(+)-Betaxolol

B

(-)-Betaxolol
93221-48-8

(-)-Betaxolol

Conditions
ConditionsYield
With diethylamine In acetonitrile Reagent/catalyst; Resolution of racemate;

63659-18-7Relevant articles and documents

The solid-state structure of the β-blocker metoprolol: a combined experimental and in silico investigation

Rossi, Patrizia,Paoli, Paola,Chelazzi, Laura,Conti, Luca,Bencini, Andrea

, p. 87 - 96 (2019/01/24)

Metoprolol {systematic name: (RS)-1-isopropylamino-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol}, C15H25NO3, is a cardioselective β1-adrenergic blocking agent that shares part of its molecular skeleton with a large number of other β-blockers. Results from its solid-state characterization by single-crystal and variable-temperature powder X-ray diffraction and differential scanning calorimetry are presented. Its molecular and crystal arrangements have been further investigated by molecular modelling, by a Cambridge Structural Database (CSD) survey and by Hirshfeld surface analysis. In the crystal, the side arm bearing the isopropyl group, which is common to other β-blockers, adopts an all-trans conformation, which is the most stable arrangement from modelling data. The crystal packing of metoprolol is dominated by an O—H…N/N…H—O pair of hydrogen bonds (as also confirmed by a Hirshfeld surface analysis), which gives rise to chains containing alternating R and S metoprolol molecules extending along the b axis, supplemented by a weaker O…H—N/N—H…O pair of interactions. In addition, within the same stack of molecules, a C—H…O contact, partially oriented along the b and c axes, links homochiral molecules. Amongst the solid-state structures of molecules structurally related to metoprolol deposited in the CSD, the β-blocker drug betaxolol shows the closest analogy in terms of three-dimensional arrangement and interactions. Notwithstanding their close similarity, the crystal lattices of the two drugs respond differently on increasing temperature: metoprolol expands anisotropically, while for betaxolol, an isotropic thermal expansion is observed.

THERAPY FOR COMPLICATIONS OF DIABETES

-

, (2009/07/02)

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.

FLUORESCENCE BASED DETECTION OF SUBSTANCES

-

, (2009/09/28)

A method for the fluorescent detection of a substance, the method comprising providing particles comprising a metal or a metal oxide core, wherein one or more optionally fluorescently tagged antibodies or human specific peptide nucleic acid (PNA) oligomers for binding to a substance is/are bound, directly or indirectly, to the surface of the metal or metal oxide; contacting a substrate, which may or may not have the substance on its surface, with the particles for a time sufficient to allow the antibody/PNA oligomer to bind with the substance; removing those particles which have not bound to the substrate; if the antibodies or PNA oligomers are not fluorescently tagged, contacting the substrate with one or more fluorophores that selectively bind with the antibody and/or substance, then optionally washing the substrate to remove unbound fluorophores; and illuminating the substrate with appropriate radiation to show the fluorophores on the substrate.

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