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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
Structure of BERAPROST SODIUM

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

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C24H29O5
Molecular Weight 397.4841
Charge -1
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 5 / 6
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 133.0 nM [Kd]
Prostacyclin receptor
9
Target ID: P43252
Gene ID: 19222.0
Gene Symbol: Ptgir
Target Organism: Mus musculus (Mouse)
Agonist
2678
 16.0 nM [Ki]
Agonist
2678
 110.0 nM [Ki]
Antagonist
2778
 63.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
DORNER

Approved Use

Improvement of ulcers, pain & feeling of coldness associated with chronic arterial occlusion. Primary pulmonary Hypertension.
Primary
Approved
8429
DORNER

Approved Use

Improvement of ulcers, pain & feeling of coldness associated with chronic arterial occlusion. Primary pulmonary Hypertension.
PubMed

PubMed

TitleDatePubMed
Protective effect of beraprost sodium, a new chemically stable prostacyclin analogue, against the deterioration of baroreceptor reflex following transient global cerebral ischaemia in dogs.
1990 Jan
Clinical evaluation on combined administration of oral prostacyclin analogue beraprost and phosphodiesterase inhibitor cilostazol.
1995 Feb
Effect of beraprost sodium, a stable prostacyclin analogue, on pulmonary thromboembolism in mice.
1995 Jan 15
A dose-effect study of beraprost sodium in intermittent claudication.
1996 Jun
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
1997 Sep
Prostacyclin analog prevents stress-induced expression of immediate early genes and gastric mucosal lesions in the rat stomach.
1999
Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial disease and pulmonary arterial hypertension.
2002
Amelioration by beraprost sodium, a prostacyclin analogue, of established renal dysfunction in rat glomerulonephritis model.
2002 Aug 2
Beraprost sodium-induced hypotension in two patients after cardiac surgery.
2006 Mar
Efficacy of oral sildenafil in a beraprost-treated patient with severe pulmonary hypertension secondary to type I glycogen storage disease.
2009 Oct
Patents

Patents

20130165400
6
WO/2004/034959A2
2
WO/2015/020153A1
2
WO/2017/027706A1
2

Sample Use Guides

In Vivo Use Guide
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:40:46 UTC 2023
Edited
by admin
on Fri Dec 15 15:40:46 UTC 2023
Record UNII
15K99VDU5F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BERAPROST SODIUM
JAN   MART.   USAN   WHO-DD  
USAN  
Official Name English
Beraprost sodium [WHO-DD]
Common Name English
PROCYLIN
Brand Name English
BERAPROST SODIUM [USAN]
Common Name English
TRK-100
Code English
SODIUM (±)-(1R,2R,3AS,8BS)-2,3,3A,8B-TETRAHYDRO-2-HYDROXY-1-((E)-(3S,4RS)-3-HYDROXY-4-METHYL-1-OCTEN-6-YNYL)-1H-CYCLOPENTA(B)BENZOFURAN-5-BUTYRATE
Common Name English
2,3,3A,8B-TETRAHYDRO-2-HYDROXY-1((E)-(3S)-3-HYDROXY-4-METHYL-1-OCTEN-6-YNYL)-1H-CYCLOPENTA(B)BENZOFURAN-5-BUTYRIC ACID SODIUM SALT
Common Name English
BERAPROST SODIUM SALT
MI  
Common Name English
TRK-100STP
Code English
BERAPROST SODIUM SALT [MI]
Common Name English
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
Common Name English
BERAPROST SODIUM [JAN]
Common Name English
MDL-201129
Code English
ML-1129
Code English
BERAPROST SODIUM [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
EU-Orphan Drug EU/3/01/053
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
Code System Code Type Description
MERCK INDEX
m2424
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C79991
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
PUBCHEM
23663404
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
CHEBI
31270
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
FDA UNII
15K99VDU5F
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
EVMPD
SUB00759MIG
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL1207745
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
CAS
88475-69-8
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
USAN
DD-17
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID2048585
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
SMS_ID
100000085021
Created by admin on Fri Dec 15 15:40:46 UTC 2023 , Edited by admin on Fri Dec 15 15:40:46 UTC 2023
PRIMARY
Related Record Type Details
Structure of BERAPROST
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BERAPROST
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