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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H29O5.Na
Molecular Weight 420.4738
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ESUBERAPROST SODIUM

SMILES

[Na+].[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)[C@@H](C)CC#CC)[C@@]1([H])C3=C(O2)C(CCCC([O-])=O)=CC=C3

InChI

InChIKey=YTCZZXIRLARSET-ZTWNIFTGSA-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
Esuberaprost (314d) is an active enantiomer of beraprost, a prostacyclin analog. The pharmacologic action of esuberaprost is mediated by specifically binding to PGI2 receptors in smooth muscle cells (the blood vessel’s endothelium) and platelets. Upon binding, the compound widened blood vessels, preventing the formation of blood clots, and lowering blood pressure in the lungs. As a result, it was expected to improve the symptoms of pulmonary arterial hypertension. United Therapeutics announced it has ended its Phase 3 BEAT trial testing esuberaprost as an add-on therapy to its product Tyvaso (inhaled treprostinil) for clinically symptomatic patients with pulmonary arterial hypertension (PAH). According to a company press release, the study failed to reach its main endpoint of delaying the time to first clinical worsening events.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P43119
Gene ID: 5739.0
Gene Symbol: PTGIR
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Specific binding of the new stable epoprostenol analogue beraprost sodium to prostacyclin receptors on human and rat platelets.
1989 Apr
Pharmacokinetics and platelet antiaggregating effects of beraprost, an oral stable prostacyclin analogue, in healthy volunteers.
1993 Nov

Sample Use Guides

Phase III study: 15 μg tablets for oral, 1 or 2 tablets four times daily (QID) administration
Route of Administration: Oral
Name Type Language
ESUBERAPROST SODIUM
USAN   WHO-DD  
USAN  
Official Name English
BERAPROST SODIUM 314D
Common Name English
ESUBERAPROST SODIUM [USAN]
Common Name English
APS-314D
Code English
GP-1681
Code English
Esuberaprost sodium [WHO-DD]
Common Name English
(+)-SODIUM 4-((1R,2R,3AS,8BS)-2-HYDROXY-1-((1E,3S,4S)-3-HYDROXY-4-METHYL-OCT-1-EN-6-YN-1-YL)-2,3,3A,8B-TETRAHYDRO-1H-CYCLOPENTA(B)(1)BENZOFURAN-5-YL)BUTANOATE
Systematic Name English
BPS-314D
Code English
GP1681
Code English
APS 314D
Code English
BERAPROST SODIUM, (+)-
Common Name English
1H-CYCLOPENTA(B)BENZOFURAN-5-BUTANOIC ACID, 2,3,3A,8B-TETRAHYDRO-2-HYDROXY-1-((1E,3S,4S)-3-HYDROXY-4-METHYL-1-OCTEN-6-YN-1-YL)-, SODIUM SALT (1:1), (1R,2R,3AS,8BS)-
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 355711
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
Code System Code Type Description
CAS
152695-53-9
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY
NCI_THESAURUS
C166926
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY
USAN
AB-81
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY
PUBCHEM
71587534
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY
ChEMBL
CHEMBL3137314
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY
SMS_ID
100000177220
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID20165105
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY
FDA UNII
6C8TLD4Q9K
Created by admin on Sat Dec 16 06:34:51 GMT 2023 , Edited by admin on Sat Dec 16 06:34:51 GMT 2023
PRIMARY