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13655-52-2

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13655-52-2 Usage

Description

Occupational cases of contact dermatitis caused by exposure to alprenolol have been reported within the pharmaceutical industry.

Originator

Aptol,Globopharm,Switz.

Uses

Antiadrenergic (β-receptor).

Definition

ChEBI: A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.

Manufacturing Process

A solution of 24.6 g of o-allyl-epoxypropoxybenzene dissolved in 250 ml of absolute ethanol saturated with ammonia was placed in an autoclave and heated on a steam-bath for 2 hours. The alcohol was then removed by distillation and the residue was redissolved in a mixture of methanol and ethylacetate. Hydrogen chloride gas was introduced into the solution. The hydrochloride salt was then precipitated by the addition of ether to yield 11.4 g of product. Five grams of the amine-hydrochloride thus formed were dissolved in 50 ml of methanol and 9 ml of acetone. The resulting solution was cooled to about 0°C. At this temperature 5 g of sodium borohydride were added over a period of 1 hour. Another 2.2 ml of acetone and 0.8 g of sodium borohydride were added and the solution was kept at room temperature for 1 hour, after which 150 ml of water were added to the solution. The solution was then extracted with three 100-ml portions of ether which were combined, dried over potassium carbonate, and evaporated. The free base was then recrystallized from petrol ether (boiling range 40-60°C) to yield 2.7 g of material having a melting point of 57°C. The corresponding hydrochloride was prepared by dissolving 2 g of the product, prepared above, in 20 ml of acetone, and adding to the resulting solution acetone saturated with hydrogen chloride until the pH was reduced to about 3. The precipitated hydrochloride salt was then recrystallized from acetone.

Therapeutic Function

Beta-adrenergic blocker

Contact allergens

Occupational cases of contact dermatitis due to this betablocker were reported in the pharmaceutical industry

Check Digit Verification of cas no

The CAS Registry Mumber 13655-52-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,5 and 5 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 13655-52:
(7*1)+(6*3)+(5*6)+(4*5)+(3*5)+(2*5)+(1*2)=102
102 % 10 = 2
So 13655-52-2 is a valid CAS Registry Number.
InChI:InChI=1/C15H23NO2.ClH/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3;/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3;1H

13655-52-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name alprenolol

1.2 Other means of identification

Product number -
Other names Alpheprol

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:13655-52-2 SDS

13655-52-2Related news

Combined pharmacokinetic and pharmacodynamic studies on Alprenolol (cas 13655-52-2) and 4-hydroxy-Alprenolol (cas 13655-52-2) in man09/27/2019

The effects of orally (100 mg) and intravenously (10 mg) administered alprenolol on the heart rate of 4 exercising healthy volunteers were correlated with the plasma concentrations of alprenolol and its metabolite 4-OH-alprenolol. The metabolite was recovered in plasma after both routes of alpre...detailed

Gel formulations containing catanionic vesicles composed of Alprenolol (cas 13655-52-2) and SDS: Effects of drug release and skin penetration on aggregate structure09/25/2019

To fully utilize the extended contact time of gel formulations a novel formulation with drug containing catanionic aggregates offering prolonged drug release and skin penetration were investigated. This study aimed to further explore the drug release process from catanionic vesicles in gels.Cata...detailed

Nasal absorption of Alprenolol (cas 13655-52-2) and metoprolol09/10/2019

In order to determine the importance of hydrophobicity in nasal drug absorption, we studied the bioavailability of the β-adrenoceptor blocking drugs, alprenolol and metoprolol, in volunteers, after nasal administration. The results were related to the oral and sublingual administration. The int...detailed

Enantioselective determination of Alprenolol (cas 13655-52-2) in human plasma by liquid chromatography with tandem mass spectrometry using cellobiohydrolase chiral stationary phases09/09/2019

A fast, sensitive, and enantioselective LC–MS/MS bioanalytical method was developed and validated for the direct determination of individual alprenolol enantiomers in human plasma using cellobiohydrolase (CBH) chiral stationary phases (CSP) along with supported liquid extraction (SLE) procedure...detailed

Electrophoretic behavior of Alprenolol (cas 13655-52-2) in mixed solvent electrolyte systems09/08/2019

The electrophoretic mobilities of alprenolol have been determined in a mixed solvent background electrolyte system containing sodium acetate (40 mM)+acetic acid (40 mM) as buffering agent and different volume fractions of water, methanol and ethanol using capillary electrophoresis. The mobility ...detailed

Enantioselective biodegradation of pharmaceuticals, Alprenolol (cas 13655-52-2) and propranolol, by an activated sludge inoculum09/07/2019

Biodegradation of chiral pharmaceuticals in the environment can be enantioselective. Thus quantification of enantiomeric fractions during the biodegradation process is crucial for assessing the fate of chiral pollutants. This work presents the biodegradation of alprenolol and propranolol using a...detailed

Labeling of Alprenolol (cas 13655-52-2) with fluorescent aryl iodide as a reagent based on Mizoroki–Heck coupling reaction09/06/2019

A novel fluorescent labeling method for alprenolol was developed based on Mizoroki–Heck coupling reaction. We designed and synthesized fluorescent aryl iodide, 4-(4,5-diphenyl-1H-imidazol-2-yl)iodobenzene (DIBI) as a labeling reagent. DIBI has a lophine skeleton carrying an iodide atom acting a...detailed

Quantification of Alprenolol (cas 13655-52-2) and propranolol in human plasma using a two-dimensional liquid chromatography (2D-LC)09/05/2019

A new two-dimensional liquid chromatography (2D-LC) method using a column switching valve, with a restricted-access media (RAM) column in the first dimension was developed and validated for the quantification of two β-blockers in human plasma. Several parameters, such as sample collection, mobi...detailed

13655-52-2Relevant articles and documents

-

Simon et al.

, (1974)

-

Continuous flow upgrading of glycerol toward oxiranes and active pharmaceutical ingredients thereof

Morodo, Romain,Gérardy, Romaric,Petit, Guillaume,Monbaliu, Jean-Christophe M.

, p. 4422 - 4433 (2019/08/21)

A robust continuous flow procedure for the transformation of bio-based glycerol into high value-added oxiranes (epichlorohydrin and glycidol) is presented. The flow procedure features a central hydrochlorination/dechlorination sequence and provides economically and environmentally favorable conditions involving an organocatalyst and aqueous solutions of hydrochloric acid and sodium hydroxide. Pimelic acid (10 mol%) shows an exceptional catalytic activity (>99% conversion of glycerol, a high selectivity toward 1,3-dichloro-2-propanol and 81% cumulated yield toward intermediate chlorohydrins) for the hydrochlorination of glycerol (140 °C) with 36 wt% aqueous HCl. These conditions are validated on a sample of crude bio-based glycerol. The dechlorination step is effective (quantitative conversion based on glycerol) with concentrated aqueous sodium hydroxide (20 °C) and can be directly concatenated to the hydrochlorination step, hence providing a ca. 2:3 separable mixture of glycidol and epichlorohydrin (74% cumulated yield). An in-line membrane separation unit is included downstream, providing usable streams of epichlorohydrin (in MTBE, with an optional concentrator) and glycidol (in water). The scalability of the dechlorination step is then assessed in a commercial pilot-scale continuous flow reactor. Next, bio-based epichlorohydrin is further utilized for the continuous flow preparation of β-amino alcohol active pharmaceutical ingredients including propranolol (hypertension, WHO essential), naftopidil (prostatic hyperplasia) and alprenolol (angina pectoris) within a concatenable two-step procedure using a FDA class 3 solvent (DMSO). This work provides the first example of direct upgrading of bio-based glycerol into high value-added pharmaceuticals under continuous flow conditions.

Asymmetric hydrolytic kinetic resolution with recyclable polymeric Co(iii)-salen complexes: A practical strategy in the preparation of (S)-metoprolol, (S)-toliprolol and (S)-alprenolol: Computational rationale for enantioselectivity

Roy, Tamal,Barik, Sunirmal,Kumar, Manish,Kureshy, Rukhsana I.,Ganguly, Bishwajit,Khan, Noor-Ul H.,Abdi, Sayed H. R.,Bajaj, Hari C.

, p. 3899 - 3908 (2015/02/19)

A series of chiral polymeric Co(iii)-salen complexes based on a number of achiral and chiral linkers were synthesized and their catalytic performances were assessed in the asymmetric hydrolytic kinetic resolution of terminal epoxides. The effects of the linker were judiciously studied and it was found that in the case of the chiral BINOL-based polymeric salen complex 1, there was an enrichment in catalyst reactivity and enantioselectivity of the unreacted epoxide, particularly in the case of short as well as long chain aliphatic epoxides. Good isolated yields of the unreacted epoxide (up to 46% compared to 50% theoretical yield) along with high enantioselectivity (up to 99%) were obtained in most cases using catalyst 1. Further studies showed that catalyst 1 could retain its catalytic activity for six cycles under the present reaction conditions without any significant loss in activity or enantioselectivity. To show the practical applicability of the above synthesized catalyst we have synthesised some potent chiral β-blockers in moderate yield and high enantioselectivity using complex 1. The DFT (M06-L/6-31+G??//ONIOM(B3LYP/6-31G?:STO-3G)) calculations revealed that the chiral BINOL linker influences the enantioselectivity achieved with Co(iii)-salen complexes. Further, the transition state calculations show that the R-BINOL linker with the (S,S)-Co(iii)-salen complex is energetically preferred over the corresponding S-BINOL linker with the (S,S)-Co(iii)-salen complex for the HKR of 1,2-epoxyhexane. The role of non-covalent C-H?π interactions and steric effects has been discussed to control the HKR reaction of 1,2-epoxyhexane.

ANTIHYPERTENSIVE THERAPY

-

, (2009/09/08)

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

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