Details
Stereochemistry | EPIMERIC |
Molecular Formula | C24H29O5.Na |
Molecular Weight | 420.4738 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 6 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)C(C)CC#CC)[C@@]1([H])C3=C(O2)C(CCCC([O-])=O)=CC=C3
InChI
InChIKey=YTCZZXIRLARSET-VJRSQJMHSA-M
InChI=1S/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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11790158Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26686607 | https://www.ncbi.nlm.nih.gov/pubmed/2665758 | http://www.astellas.co.id/product/view/4/5
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11790158
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26686607 | https://www.ncbi.nlm.nih.gov/pubmed/2665758 | http://www.astellas.co.id/product/view/4/5
Beraprost is a stable, orally active prostacyclin analogue. Beraprost acts by binding to prostacyclin membrane receptors ultimately inhibiting the release of Ca2+ from intracellular storage sites. This reduction in the influx of Ca2+ has been postulated to cause relaxation of the smooth muscle cells and vasodilation. Beraprost is indicated for the treatment of pulmonary hypertension and improvement of ulcers, pain & feeling of coldness associated with chronic arterial occlusion. In addition beraprost displays thyroid hormone receptor antagonistic properties.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1995 |
133.0 nM [Kd] | ||
Target ID: P43252 Gene ID: 19222.0 Gene Symbol: Ptgir Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10508233 |
16.0 nM [Ki] | ||
Target ID: CHEMBL4336 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10508233 |
110.0 nM [Ki] | ||
Target ID: CHEMBL2111462 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26686607 |
63.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DORNER Approved UseImprovement of ulcers, pain & feeling of coldness associated with chronic arterial occlusion. Primary pulmonary Hypertension. |
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Primary | DORNER Approved UseImprovement of ulcers, pain & feeling of coldness associated with chronic arterial occlusion. Primary pulmonary Hypertension. |
PubMed
Title | Date | PubMed |
---|---|---|
Clinical evaluation on combined administration of oral prostacyclin analogue beraprost and phosphodiesterase inhibitor cilostazol. | 1995 Feb |
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Effect of beraprost sodium, a stable prostacyclin analogue, on pulmonary thromboembolism in mice. | 1995 Jan 15 |
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A dose-effect study of beraprost sodium in intermittent claudication. | 1996 Jun |
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Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. | 1997 Sep |
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Prostacyclin analog prevents stress-induced expression of immediate early genes and gastric mucosal lesions in the rat stomach. | 1999 |
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Comparative effects of beraprost, a stable analogue of prostacyclin, with PGE(1), nitroglycerin and nifedipine on canine model of vasoconstrictive pulmonary hypertension. | 2001 Mar |
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Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial disease and pulmonary arterial hypertension. | 2002 |
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Adaptive HNE-Nrf2-HO-1 pathway against oxidative stress is associated with acute gastric mucosal lesions. | 2008 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.astellas.co.id/product/view/4/5
Improvement of ulcers, pain & feeling of coldness associated with chronic arterial occlusion, Adult : 120 mcg daily in 3 divided doses.
Primary pulmonary Hypertension: 60 mcg daily in 3 divided doses. Gradually increase dose if needed, up to a max of 180 mcg daily in 3-4 divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10213178
In suppressing platelet aggregation beraprost was especially potent with IC50 of 0.2-0.5 nM when platelets were activated by U46619, a thromboxane A2 analogue, or low concentrations of collagen which activates platelets through thromboxane A2 production. The IC50 values were 2-5 nM with ADP and epinephrine, which induce the formation of small aggregates independently of thromboxane A2 production.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C78568
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EU-Orphan Drug |
EU/3/01/053
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m2424
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C79991
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23663404
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31270
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15K99VDU5F
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SUB00759MIG
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CHEMBL1207745
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88475-69-8
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DD-17
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DTXSID2048585
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100000085021
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ACTIVE MOIETY
SUBSTANCE RECORD