Epoprostenol

Base Information

• Chemical Name: Epoprostenol
• CAS No.: 35121-78-9
• Deprecated CAS: 63748-50-5,63859-31-4
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• UNII: DCR9Z582X0
• DSSTox Substance ID: DTXSID5022988
• Nikkaji Number: J17.550A
• Wikipedia: Prostacyclin
• Wikidata: Q412050
• NCI Thesaurus Code: C61748
• RXCUI: 8814
• Pharos Ligand ID: QFY18N3QPJ2R
• Metabolomics Workbench ID: 2446
• ChEMBL ID: CHEMBL1139
• Mol file: 35121-78-9.mol

Synonyms:Epoprostanol;Epoprostenol;Epoprostenol Sodium;Epoprostenol Sodium Salt, (5Z,9alpha,11alpha,13E,15S)-Isomer;Flolan;Prostacyclin;Prostaglandin I(2);Prostaglandin I2;Veletri

Chemical Property of Epoprostenol

Chemical Property:

• Vapor Pressure: 1.86E-13mmHg at 25°C
• Refractive Index: 1.611
• Boiling Point: 530.2°Cat760mmHg
• PKA: 4.70±0.10(Predicted)
• Flash Point: 182.1°C
• PSA: 89.82000
• Density: 1.221g/cm³
• LogP: 2.07380
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 485

Purity/Quality:

98%,99%, ^*data from raw suppliers

Epoprostenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC2C1CC(=CCCCC(=O)O)O2)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O)O
• Recent ClinicalTrials: VentaProst in Subjects With COVID-19 Requiring Mechanical Ventilation
• Recent EU Clinical Trials: Combined drug Approach to Prevent Ischemia-reperfusion injury during Transplantation of Livers (CAPITL): a first-in-men study
• Recent NIPH Clinical Trials: ACT-385781A extension study for PAH pediatric patients
• Uses: Inhibitor (platelet). [Names previously used: Prostacyclin, PGI2, Prostagland in I2, Prostaglandin X, PGX].
• Therapeutic Function: Platelet aggregation inhibitor, Antimetastatic

Technology Process of Epoprostenol

There total 6 articles about Epoprostenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

[3aR-[3aα,4α(E),5β,6aα]]-1-(6,6-Difluorohexahydro-2,5-dihydroxy-2H-cyclopenta[b]furan-4-yl)-1-octen-3-one + trimethyl orthoformate (149-73-5) → Epoprostenol (35121-78-9)

Guidance literature:

With hydrogenchloride; sodium borohydrid; In methanol; CeCl₃; water; acetonitrile;

Reference yield:

5,6-didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGF2α methyl ester (59926-53-3) → Epoprostenol (35121-78-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Hg(II) trifluoroacetate, N(C₂H₅)3, 2) NaBH₄, NaOMe / 1) THF, -78 deg C, 1 h, 2) THF - MeOH, -78 deg C, 1 h

2: 74 percent / tetrabutylammoniumfluoride / tetrahydrofuran / 15 h / 15 °C

3: alkaline hydrolysis

With sodium tetrahydroborate; Hg(II) trifluoroacetate; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86399-6

Reference yield:

11,15-O-bis(tert-butyldimethylsilyl)PGI2 methyl ester (78824-82-5) → Epoprostenol (35121-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / tetrabutylammoniumfluoride / tetrahydrofuran / 15 h / 15 °C

2: alkaline hydrolysis

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86399-6

upstream raw materials:

PGI₂ methyl ester

5,6-didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGF_2α methyl ester

11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester

trimethyl orthoformate

Downstream raw materials:

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-6-oxo-heptanoic acid

Refernces

• 1、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.
• 2、 -. "Method for treating resistant hypertension". . . Retrieved 2008/06/13.