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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 of ESUBERAPROST

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

PubMed

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
Record UNII
1JSN1I7582
Record Status Validated (UNII)
Record Version