ESUBERAPROST

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H30O5
Molecular Weight	398.492
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[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=CTPOHARTNNSRSR-NOQAJONNSA-N

InChI=1S/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

HIDE SMILES / InChI

Molecular Formula	C24H30O5
Molecular Weight	398.492
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800040766 | https://pulmonaryhypertensionnews.com/2019/04/11/united-therapeutics-ends-clinical-development-of-esuberaprost-as-add-on-therapy-for-pah/

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostacyclin receptor 9 Target ID: P43119 Gene ID: 5739.0 Gene Symbol: PTGIR Target Organism: Homo sapiens (Human) Sources: https://www.covance.com/content/dam/covance/assetLibrary/posters/PatelACCP16-BPS-314d-MR-Warfarin.pdf	Binding Agent 1064

PubMed

Title	Date	PubMed
Specific binding of the new stable epoprostenol analogue beraprost sodium to prostacyclin receptors on human and rat platelets.	1989 Apr	2665758
Pharmacokinetics and platelet antiaggregating effects of beraprost, an oral stable prostacyclin analogue, in healthy volunteers.	1993 Nov	7506323

Sample Use Guides

In Vivo Use Guide

Phase III study: 15 μg tablets for oral, 1 or 2 tablets four times daily (QID) administration

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:40:54 GMT 2023` Edited by `admin` on `Sat Dec 16 06:40:54 GMT 2023`
Record UNII	1JSN1I7582
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESUBERAPROST

Official 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-YNYL)-, (1R,2R,3AS,8BS)-

Common Name

English

(+)-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)BUTANOIC ACID

Systematic Name

English

Esuberaprost [WHO-DD]

Common Name

English

esuberaprost [INN]

Common Name

English

BERAPROST, (+)-

Common Name

English

APS-314D FREE ACID

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL3137314