88430-50-6 Usage
Uses
Platelet aggregation inhibitor; stable analog of Prostacyclin. Antithrombotic; vasodilator (peripheral).
Mechanism of action
Beraprost is a chemically stable, oral form of prostacyclin that is readily absorbed from GI
tract. Like natural prostacyclin, beraprost dilates blood vessels, prevents platelet aggregation, and prevents
proliferation of smooth muscle cells surrounding blood vessels. It may be an important treatment for early stage PVD
and for early stage pulmonary hypertension. Intermittent oral doses of beraprost, however, do not seem to provide the
consistent blood levels
necessary to treat the advanced stages of pulmonary hypertension.
Clinical Use
Beraprost is an oral formulation of a prostacyclin analog for the treatment of early stage pulmonary hypertension as
well as early stage PVD.
Side effects
Adverse
effects include headache, flushing, jaw pain, and diarrhea.
Enzyme inhibitor
This orally active epoprostenol analogue (FW = 398.50 g/mol; CAS 88475-
69-8; Soluble to 25 mM in DMSO), also named TRA-418 and 2,3,3a,8b-
tetrahydro-2-hydroxy-1- (3-hydroxy-4-methyl-1-octen-6-yn-1-yl) -1H-
cyclopenta[b]benzofuran-5-butanoic acid, is a potent agonist for the
Prostacyclin Receptor, a member of the G-protein coupled receptor family.
Prostacyclin, the major product of cyclooxygenase in macrovascular
endothelium, elicits a potent vasodilation and inhibition of platelet
aggregation through binding to this receptor. Beraprost potently inhibits
ADP-induced platelet aggregation (pIC50 = 8.26) and P-selectin expression
in vitro (pIC50 = 8.56). It also increases vasodilation and reduces pulmonary
hypertension in vivo. TRA-418 inhibited platelet GPIIb/IIIa activation as
well as induction of P-selectin expression by adenosine 5'-diphosphate,
Thrombin Receptor Agonist Peptide 1-6 (Ser-Phe-Leu-Leu-Arg-Asn-NH2),
and U-46619 in the presence of epinephrine. TRA-418 also inhibits
platelet aggregation induced by those platelet-stimulants in Ca2+-chelating
anticoagulant, citrate and in nonchelating anticoagulant, d-phenylalanyl-l-
prolyl-l-arginyl-chloromethyl ketone (PPACK). The TP-receptor antagonist
SQ-29548 inhibited only U-46619+epinephrine-induced GPIIb/IIIa
activation, P-selectin expression, and platelet aggregation. The IP-receptor
agonist beraprost sodium inhibited platelet activation. Beraprost also
inhibited platelet aggregation induced by platelet stimulants we tested in
citrate and in PPACK. The GPIIb/IIIa inhibitor abciximab blocked
GPIIb/IIIa activation and platelet aggregation. However, abciximab showed
slight inhibitory effects on P-selectin expression. TRA-418 is more
advantageous as an antiplatelet agent than TP-receptor antagonists or IP-
receptor agonists separately used. TRA-418 showed a different inhibitory
profile from abciximab in the effects on P-selectin expression.
Check Digit Verification of cas no
The CAS Registry Mumber 88430-50-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,8,4,3 and 0 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 88430-50:
(7*8)+(6*8)+(5*4)+(4*3)+(3*0)+(2*5)+(1*0)=146
146 % 10 = 6
So 88430-50-6 is a valid CAS Registry Number.
InChI:InChI=1/C24H30O5/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)/b13-12+/t15?,17-,19+,20+,21-,23-/m0/s1
88430-50-6Relevant articles and documents
Preparation method of beraprost sodium
-
, (2021/10/05)
The invention discloses a preparation method of a beraprost sodium intermediate. According to the preparation method, the synthesis route is shortened, the reaction condition is mild, and the operation is simple and convenient; the raw materials are cheap and easy to obtain, use of highly toxic and polluting reagents is avoided, and the cost is reduced; the product yield is obviously improved, and the method is suitable for industrial production.
Beraprost-314d crystals and methods for preparation thereof
-
Page/Page column 8, (2020/03/18)
The present invention provides crystalline Forms II and III of Beraprost-314d, and processes for the preparation thereof.
Synthetic method of beraprost
-
Paragraph 0059-0063; 0074-0076; 0077-0078; 0084, (2020/05/30)
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.
