88475-69-8

Basic information

• Product Name: Beraprost sodium
• Synonyms: beraprostsodium;ML 1129;PROCYLIN;TRK 100;BERAPROST SODIUM SALT;2,3,3A-8B-TETRAHYDRO-2-HYDROXY-1-(3-HYDROXY-4-METHYL-1-OCTEN-6-YNYL)-1H-CYCLOPENTA[B]BENZOFURAN-5-BUTANOIC ACID, SODIUM SALT;1H-Cyclopenta[b]benzofuran-5-butanoic acid, 2,3,3a,8b-tetrahydro-2-hydroxy-1-(3-hydroxy-4-methyl-1-octen-6-ynyl)-, monosodium salt;Dorner
• CAS NO: 88475-69-8
• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 420.47
• Product Categories: Prostaglandins;Prostaglandin;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 88475-69-8.mol

Chemical Properties

• Melting Point: 204-206°C
• Boiling Point: 572.1 °C at 760 mmHg
• Flash Point: 193.1 °C
• Appearance: white solid
• Vapor Pressure: 6.32E-14mmHg at 25°C
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• CAS DataBase Reference: Beraprost sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Beraprost sodium(88475-69-8)
• EPA Substance Registry System: Beraprost sodium(88475-69-8)

Safety Data

• Hazardous Substances Data: 88475-69-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Beraprost sodium is used as an antithrombotic agent for the treatment of peripheral vascular diseases such as Raynaud's syndrome and Buerger's disease. Its application is due to its ability to inhibit platelet aggregation and improve clinical endpoints in diseases responsive to prostacyclin.
Used in Cardiovascular Applications:
Beraprost sodium is used as a therapeutic agent for primary pulmonary hypertension, improving the survival and pulmonary hemodynamics of patients. It is administered orally in doses of 20-100 μg, given 1 to 3 times per day, to achieve the desired clinical effects.
Used in Research and Development:
Beraprost sodium is used as a research compound for studying the effects of prostacyclin analogs on platelet aggregation and their potential applications in various cardiovascular and vascular diseases. Its chemical properties as a white solid make it suitable for formulation and administration in pharmaceutical products.

Originator

Toray (Japan)

Biochem/physiol Actions

Beraprost sodium is used as a therapeutic agent for chronic artery obstructions or primary pulmonary hypertension. In individuals with coronary artery disease, beraprost sodium helps to reduce oxidative stress and developed forearm endothelium dependent vasodilation.

InChI:InChI=1/C24H30O5.Na/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28;/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28);/q;+1/p-1/b13-12+;/t15?,17-,19+,20+,21-,23-;/m0./s1

Upstream product

• 88277-23-0 4-((1R,2R,3aS,8bS)-2-Acetoxy-1-formyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester 
• 70073-58-4 dimethyl (2-oxo-3-methylhept-5-ynyl)-phosphonate 
• 474070-68-3 C₁₇H₂₀O₅ 
• 88295-11-8 4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester 
• 88277-19-4 methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate 

Relevant articles and documents

Synthetic method of beraprost

The invention relates to a synthetic method of beraprost. The synthetic method comprises the following steps: with an intermediate I as an initial raw material, carrying out selective primary alcoholoxidation and a Witting reaction to obtain an intermediate V; carrying out reduction and column chromatography purification on the intermediate V to obtain an intermediate IV; and hydrolyzing the intermediate IV to obtain beraprost. According to the synthetic method disclosed by the invention, two hydroxyl groups of the intermediate I are selectively oxidized, so a hydroxyl protection reagent is prevented from being used; in the oxidation step, ultralow-temperature (-60 to -80 DEG C) reactions and use of a reagent DCC with relatively high toxicity are avoided; in the reduction step, diisobutylaluminum hydride is prevented from being used; process operation units are greatly reduced, reaction steps are shortened, emission of three wastes is reduced, and the reactions are more efficient andenvironment-friendlier; and the main peak content of the prepared beraprost reaches 99.0% or above, and total process yield reaches 26% or above. The invention provides the synthetic method which ismore beneficial for industrial production.

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.

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.

Method for treating resistant hypertension

A method is provided for lowering blood pressure in a patient having clinically diagnosed resistant hypertension. The method comprises administering darusentan to the patient adjunctively with a baseline antihypertensive regimen that comprises administration of at least one diuretic and at least two antihypertensive drugs selected from at least two of (a) ACE inhibitors and angiotensin II receptor blockers, (b) beta-adrenergic receptor blockers and (c) calcium channel blockers. The darusentan is orally administered at a dose and frequency effective, in combination with the baseline regimen, 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.

USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS

The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula