75659-07-3

Basic information

• Product Name: DILEVALOL
• Synonyms: DILEVALOL;DILEVALOL HCL;Dilevaol;2-Hydroxy-5-[(R)-1-hydroxy-2-[[(R)-1-methyl-3-phenylpropyl]amino]ethyl]benzamide;Sch-19927;(-)-5-((1R)-1-Hydroxy-2-((1R)-1-methyl-3-phenylpropylamino)ethyl)salicylamid [iupac];(R,R)-Labetalol;2-Hydroxy-5-((1R)-1-hydroxy-2-(((1R)-1-methyl-3-phenylpropyl)amino)ethyl)benzamide
• CAS NO: 75659-07-3
• Molecular Formula: C₁₉H₂₄N₂O₃
• Molecular Weight: 328.41
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 75659-07-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 552.7°C at 760 mmHg
• Flash Point: 288.1°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 4.75E-13mmHg at 25°C
• Refractive Index: 1.609
• PKA: 8.21±0.31(Predicted)
• CAS DataBase Reference: DILEVALOL(CAS DataBase Reference)
• NIST Chemistry Reference: DILEVALOL(75659-07-3)
• EPA Substance Registry System: DILEVALOL(75659-07-3)

Safety Data

• Hazardous Substances Data: 75659-07-3(Hazardous Substances Data)

Usage

Description

Dilevalol, also known as Levadil or Dilevalon, is a "dual-mechanism" antihypertensive medication that is suitable for a wide range of patients. It is the R,R-isomer of labetalol and functions as a specific competitive antagonist at both αand β-adrenergic receptor sites. Its unique mechanism of action involves a partial beta2-agonist effect that induces vasodilation, while its beta1-antagonist component helps protect against stress-induced hemodynamic changes without affecting cardiac output.

Uses

Used in Pharmaceutical Industry:
Dilevalol is used as an antihypertensive agent for the treatment of hypertension. It helps regulate blood pressure by blocking the effects of certain stress hormones and inducing vasodilation, making it a valuable medication for managing high blood pressure in various patient populations.
Used in Cardiovascular Applications:
As a dual-mechanism antihypertensive, Dilevalol is also used in the management and treatment of cardiovascular conditions. Its ability to protect against stress-induced hemodynamic changes without altering cardiac output makes it a beneficial option for patients with heart-related issues who require blood pressure regulation.

World Health Organization (WHO)

Dilevalol, a beta-adrenoreceptor antagonist, was introduced into medicine in 1989 for the treatment of hypertension. Shortly afterwards, its use became associated with isolated cases of hepatic toxicity. Although few cases were reported, the manufacturer discontinued sales in Japan and Portugal, the only countries where the drug was marketed, and withdrew applications for registration elsewhere.

InChI:InChI=1/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)/t13-,18+/m1/s1

Upstream product

• 2344-70-9 1-phenyl-3-butanol 
• 73866-23-6 5-(2-bromoacetyl)-2-hydroxybenzamide 
• 81579-50-2 2-hydroxy-5-<acetyl>benzamide 
• 36894-69-6 labetaol 
• 81580-36-1 (R)-2-hydroxy-5-<acetyl>benzamide 
• 75615-55-3 *,R^*)>-5-<1-hydroxy-2-ethyl>-2-(phenylmethoxy)benzamide 
• 2550-26-7 4-Phenyl-2-butanone 
• 937-52-0 (R)-1-methyl-3-phenylpropylamine 
• 75659-06-2 (+)-(R)-α-methyl-N-(phenylmethyl)benzenepropanamine 
• 4187-36-4 ((R)-1-Methyl-3-phenyl-propyl)-[1-phenyl-meth-(E)-ylidene]-amine 
• 88976-53-8 *,R^*)>-α-methyl-N-(1-phenylethyl)benzenepropanamide 
• 264232-40-8 2-Hydroxy-5-[1-hydroxy-2-((R)-1-methyl-3-phenyl-propylamino)-ethyl]-benzamide 
• 127988-63-0 5-{(R)-[(1-methyl-3-phenylpropyl)amino]acetyl} salicylamide 

Downstream Products

• 81585-06-0 *,S^*)>-5-<1-hydroxy-2-ethyl>-2-(phenylmethoxy)benzamide 
• 75615-56-4 *,R^*)>-5-<1-hydroxy-2-ethyl>-2-(phenylmethoxy)benzamide 
• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 76143-20-9 5-formyl-2-hydroxy-benzamide 
• 83167-32-2 (S,R)-labetalol 
• 83167-24-2 *)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide 
• 83167-31-1 *)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide 
• 636595-41-0 5-(2-bromoethoxymethyl)-2-hydroxybenzamide 
• 636595-52-3 2-hydroxy-5-(4-hydroxy-but-2-ynyloxymethyl)-benzamide 
• 636595-48-7 2-hydroxy-5-[2-(2-hydroxyethoxy)ethoxymethyl]benzamide 
• 636595-50-1 2-hydroxy-5-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxymethyl}-benzamide 
• 636595-81-8 5-{4-[3-(4-cyano-3-trifluoromethyl-phenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]-but-2-ynyloxymethyl}-2-hydroxy-benzamide 
• 636595-74-9 4-{3-[4-(2,2-dimethyl-4-oxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-ylmethoxy)but-2-ynyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrile 
• 636595-68-1 4-(3-{2-[2-(2,2-dimethyl-4-oxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-ylmethoxy)-ethoxy]-ethyl}-4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-2-trifluoromethyl-benzonitrile 

Relevant articles and documents

Preparation method of labetalol hydrochloride

The invention provides a preparation method of labetalol hydrochloride, and belongs to the technical field of medicines. The invention provides a preparation method. The method comprises the following steps: carrying out nucleophilic substitution reaction on 5-halogenated acetyl salicylamide serving as an initial raw material and benzylamine, and then carrying out nucleophilic substitution reaction on the obtained product and 3-halogenated butylbenzene (or carrying out amine-ester exchange reaction on the obtained product and an esterification reaction product of 3-hydroxybutylbenzene and p-toluenesulfonyl chloride); and carrying out catalytic hydrogenation reaction and salifying to obtain the labeolol hydrochloride. According to the preparation method provided by the invention, benzylamine is adopted to replace dibenzylamine, so that the raw materials are high in atom utilization rate and environment-friendly, and atom economy of green chemistry is embodied; wherein the amine-ester exchange reaction is high in selectivity, and the obtained product is directly used for the next-step reaction. The one-step method is adopted to remove the protective agent and reduce carbonyl, so that the process route is shortened; meanwhile, the preparation method is simple and convenient to operate, high in stability and controllability, high in production cost, high in yield and suitable for industrial production.

COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE

To characterize the urinary exosome miRNome, microarrays were used to identify the miRNA spectrum present within urinary exosomes from ten individuals that were previously classified for their salt sensitivity status. The present application discloses distinct patterns of selected exosomal miRNA expression that were different between salt-sensitive (SS), salt-resistant (SR), and inverse salt-sensitive (ISS) individuals. These miRNAs can be useful as biomarkers either individually or as panels comprising multiple miRNAs. The present invention provides compositions and methods for identifying, diagnosing, monitoring, and treating subjects with salt sensitivity of blood pressure. The applications discloses panels of miRNAs useful for comparing profiles, and in some cases one or more of the miRNAs in a panel can be used. The miRNAs useful for distinguishing SS and SR or ISS and SR subjects. One or more of the 45 miRNAs can be used. Some of the miRNAs have not been previously reported to be circulating. See those miRNAs with asterisks in FIG. 1 and below. The present invention encompasses the use of one or more of these markers for identifying and diagnosing SR, SS, and ISS subjects.

ANTIHYPERTENSIVE THERAPY

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.