Beraprost sodium CAS 88475-69-8

Introduction：Basic information about Beraprost sodium CAS 88475-69-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Beraprost sodium 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: 88475-69-8
• MF: C24H29NaO5
• MW: 420.47
• Product Categories: Prostaglandin;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Prostaglandins
• Mol File: 88475-69-8.mol

Beraprost sodium Chemical Properties

• Melting point: 204-206°C
• storage temp.: -20°C
• solubility: DMF:77.0(Max Conc. mg/mL);183.12(Max Conc. mM) Ethanol:20.0(Max Conc. mg/mL);47.56(Max Conc. mM) PBS (pH 7.2):19.0(Max Conc. mg/mL);45.19(Max Conc. mM)
• form: powder
• color: white to beige
• Water Solubility: H2O: 20mg/mL, clear
• InChIKey: YTCZZXIRLARSET-LIIFYGAANA-M
• SMILES: [C@H]12[C@H](C[C@@H](O)[C@@H]1/C=C/[C@@H](O)C(C)CC#CC)OC1C(=CC=CC2=1)CCCC([O-])=O.[Na+] |&1:0,1,3,5,8,r|
• CAS DataBase Reference: 88475-69-8(CAS DataBase Reference)

Safety Information

• WGK Germany: WGK 3
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Beraprost sodium Usage And Synthesis

Description

Beraprost sodium is a new, orally active antithrombotic epoprostenol analog introduced as a treatment for peripheral vascular disease, including Raynaud's syndrome andBuerger's disease. The antiplatelet activity may be due to its elevation of cyclic AMPin platelets which is achieved by activating adenylate cyclase in the platelet membrane,followed by the inhibition ofCa⁺⁺- influx and thromboxane A2 formation.

Description

Beraprost is an analog of prostacyclin in which the unstable enol-ether has been replaced by a benzofuran ether function. This modification increases the plasma half-life from 30 seconds to several hours, and permits the compound to be taken orally. Doses of 20-100 μg in humans, given 1 to 3 times per day, have been demonstrated to improve clinical end points in diseases responsive to prostacyclin. Oral beraprost therapy improved the survival and pulmonary hemodynamics of patients with primary pulmonary hypertension. Beraprost inhibits platelet aggregation in healthy subjects and in diabetic patients at similar doses.

Chemical Properties

White Solid

Originator

Toray (Japan)

Uses

Platelet aggregation inhibitor; stable analog of Prostacyclin. Antithrombotic; vasodilator (peripheral).

Definition

ChEBI: Beraprost sodium is the organic sodium salt of beraprost. It is used in the treatment of chronic arterial occlusive disease and primary pulmonary hypertension in Japan. It has a role as an antihypertensive agent, a platelet aggregation inhibitor, a prostaglandin receptor agonist, a vasodilator agent and an anti-inflammatory agent. It contains a beraprost(1-).

Brand name

Dorner; Dorner;Procylin

General Description

Beraprost sodium is an orally active prostacyclin analog.

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.

Side effects

Disease-related events had similar incidence in patients receiving beraprost and those receiving placebo. Drug-related adverse events like headache, flushing, jaw pain, and diarrhea were more common in patients treated with beraprost sodium and occurred mostly during the six-week titration period. The incidence was markedly reduced in the maintenance period. Six patients (9%) in the beraprost sodium group and two (3%) in the placebo group withdrew prematurely from the study because of adverse events. No clinically adverse changes in hematologic or biochemical variables were seen in the beraprost sodium group.

References

[1] NORITOSHI NAGAYA MD  Masaaki U M, PHD  Toru S M  Yoshiaki Okano MD, PHD  Shingo K M, et al. Effect of orally active prostacyclin analogue on survival of outpatients with primary pulmonary hypertension[J]. Journal of the American College of Cardiology, 1999, 34 4: Pages 1188-1192. DOI: 10.1016/s0735-1097(99)00312-5
[2] P. NONY. Platelet-aggregation inhibition and hemodynamic effects of beraprost sodium, a new oral prostacyclin derivative: a study in healthy male subjects.[J]. Canadian journal of physiology and pharmacology, 1996, 74 8 1: 887-893. DOI: 10.1139/y96-088
[3] H KATO. Effect of beraprost sodium, a stable prostaglandin I2 analogue, on platelet aggregation in diabetes mellitus.[J]. International journal of clinical pharmacology research, 1996, 16 4-5: 99-102.
[4] SHAFIQUE AHMAD. Ameliorative Effect of Beraprost Sodium on Celecoxib Induced Cardiotoxicity in Rats.[J]. Iranian Journal of Pharmaceutical Research, 2018, 17 1: 155-163.