133242-30-5

Basic information

• Product Name: Landiolol
• Synonyms: [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-2-hydroxy-3-[2-(morpholine-4-carbonylamino)ethylamino]propoxy]phenyl]propanoate;Landiolol;((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((S)-2-hydroxy-3-((2-(morpholine-4-carboxamido)ethyl)amino)propoxy)phenyl)propanoate;Benzenepropanoic acid, 4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-, [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester
• CAS NO: 133242-30-5
• Molecular Formula: C₂₅H₃₉N₃O₈
• Molecular Weight: 509.59
• EINECS: 1592732-453-0
• Mol File: 133242-30-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 727.513 °C at 760 mmHg
• Flash Point: 393.786 °C
• Appearance: /
• Density: 1.201 g/cm³
• CAS DataBase Reference: Landiolol(CAS DataBase Reference)
• NIST Chemistry Reference: Landiolol(133242-30-5)
• EPA Substance Registry System: Landiolol(133242-30-5)

Safety Data

• Hazardous Substances Data: 133242-30-5(Hazardous Substances Data)

Usage

Description

Landiolol was launched as iv infusion for the treatment of tachyarrhythmia during surgery. This structurally related derivative of esmolol can be synthesized in 3 linear steps from 3-(4-hydroxyphenyl)propionic acid by successive esterification followed by alkylation of the phenol function with (2S)-glycidyltosylate and opening of the resulting epoxide by the appropriate amine. Landiolol is an ultra short acting PI-adrenergic blocker more cardioselective (βI/β2 = 255) than esmolol (βi/β2 = 32). It showed 6-8 times greater efficiency compared to esmolol in reducing isoproterenol-induced increase in heart rate and ventricular contraction in anesthetized dogs. In clinical trials, landiolol was effective against a variety of arrhythmias with efficacy seen in patients with atrial fibrillation, proxysmal supraventricular tachycardia, ventricular tachycardia and premature complexes. Landiolol produced a doserelated pharmacokinetic behavior, has a rapid onset of action (10 min.) and is rapidly hydrolyzed to inactive acidic metabolites by esterases after iv administration. This results in an ultra-short half-life (approx. 3 min.) and p-blocade, allowing rapid termination of the drug effect by termination of infusion if side effects occur. Hypertension was the most frequent adverse event and resolved in less than 30 min. after drug withdrawal.

Originator

Ono Pharmaceutical (Japan)

Brand name

Onoact

InChI:InChI=1/C25H39N3O8.ClH/c1-25(2)35-17-22(36-25)21(14-23(30)32-3)18-4-6-20(7-5-18)34-16-19(29)15-26-8-9-27-24(31)28-10-12-33-13-11-28;/h4-7,19,21-22,26,29H,8-17H2,1-3H3,(H,27,31);1H/t19-,21?,22+;/m0./s1

Upstream product

• 69630-16-6 N-(2-aminoethyl)-4-morpholine carboxamide 
• 144256-12-2 2,2-dimethyl-1,3-dioxolan-4S-ylmethyl 3-<4-<2(S),3-epoxypropoxy>phenyl>propionate 
• 88017-03-2 2-(morpholine-4-carboxamido)ethanamino hydrochloride 
• 1398109-46-0 (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((2R)-3-chloro-2-hydroxypropoxy)phenyl)propanoate 
• 110-91-8 morpholine 
• 154467-16-0 N-(2-aminoethyl)-4-morpholine carboxamide oxalic acid 
• 144256-11-1 3-(4-hydroxyphenyl)propionic acid [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 93605-74-4 4-[(1H-imidazol-1-yl)carbonyl]morpholine 
• 501-97-3 4-hydroxyphenylpropionic acid 

Downstream Products

• 144481-98-1 Landiolol hydrochloride 
• 1253907-79-7 landiolol hydrochloride 

Relevant articles and documents

Method for preparing landiolol hydrochloride

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to an improved method for preparing landiolol and a compound shown as a formula 8. The compound shown as the formula 8 is prepared by reacting a compound shown as a formula 7 with AH (organic amine). The invention also relates to compounds of general formula 7.

Preparation method of landiolol hydrochloride

The invention provides a preparation method of landiolol hydrochloride. The preparation method utilizes cheap and easily available raw materials. A key reaction utilizes a phase transfer catalysis method so reaction time is shortened. The preparation meth

THERAPY FOR COMPLICATIONS OF DIABETES

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.