Treprostinil

Base Information

• Chemical Name: Treprostinil
• CAS No.: 81846-19-7
• Molecular Formula: C23H34O5
• Molecular Weight: 390.52
• European Community (EC) Number: 695-793-9,808-233-7
• UNII: RUM6K67ESG
• DSSTox Substance ID: DTXSID901021654
• Nikkaji Number: J430.982K
• Wikipedia: Treprostinil
• Wikidata: Q3495231
• NCI Thesaurus Code: C61983
• RXCUI: 343048
• Pharos Ligand ID: 466RVG5KZ99Y
• Metabolomics Workbench ID: 42742
• ChEMBL ID: CHEMBL1237119
• Mol file: 81846-19-7.mol

Synonyms:((1R,2R,3AS,9AS)-2-hydroxy-1-((3S)-3-hydroxyoctyl)-2,3,3A,4,9,9A-hexahydro-1H-cylopent(b)naphthalen-5-yl)oxy)acetate;Orenitram;Remodulin;trepostinil sodium;treprostinil;treprostinil diethanolamine;treprostinil diolamin;treprostinil diolamine;treprostinil sodium;UT-15;UT-15C

Chemical Property of Treprostinil

Chemical Property:

• Vapor Pressure: 1.25E-14mmHg at 25°C
• Melting Point: 121-123°
• Refractive Index: 1.553
• Boiling Point: 587.1 °C at 760 mmHg
• PKA: 3.19±0.10(Predicted)
• Flash Point: 199.3 °C
• PSA: 89.82000
• Density: 1.158 g/cm³
• LogP: 2.24850
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 390.24062418
• Heavy Atom Count: 28
• Complexity: 495

Purity/Quality:

99% ^*data from raw suppliers

Treprostinil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CCC1C(CC2C1CC3=C(C2)C(=CC=C3)OCC(=O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](CC[C@H]1[C@@H](C[C@H]2[C@@H]1CC3=C(C2)C(=CC=C3)OCC(=O)O)O)O
• Recent ClinicalTrials: Safety and Efficacy of Treprostinil in Ischemia and Reperfusion Injury in Adult Orthotopic Liver Transplantation
• Recent EU Clinical Trials: A Randomized, Double-blind, Placebo-controlled, Multinational, Phase 3 Study of the Efficacy and Safety of Inhaled Treprostinil in Subjects with Idiopathic Pulmonary Fibrosis (TETON-2)
• Recent NIPH Clinical Trials: MD-711 Phase 2/3 Study in PAH
• Uses: Synthetic analog of Prostacyclin (P839060). Antihypertensive. Treprostinil, marketed under the trade name Remodulin is a medication used to treat pulmonary arterial hypertension (PAH).
• Clinical Use: Treprostinil is a synthetic, stable form of prostacyclin for the treatment for advanced pulmonary hypertension with NYHA class III or IV symptoms as well as for late-stage peripheral vascular disease (PVD). Its sodium salt injectable form is administered either as a continuous subcutaneous infusion directly into the skin or, if the subcutaneous infusion is not tolerated, as a continuous IV infusion without an implanted catheter.

Technology Process of Treprostinil

There total 149 articles about Treprostinil 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: 100.0%

2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester (81845-98-9) → treprostinil (81846-19-7)

Guidance literature:

With sodium hydroxide; In ethanol; water;

Reference yield: 98.0%

2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester (1355990-07-6) → treprostinil (81846-19-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;

Reference yield: 97.0%

2-hydroxy-N-(2-hydroxyethyl)-N-methylethanaminium 2-(((1R,2R,3aS,9aS)-2-hydroxy-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yl)oxy)acetate → treprostinil (81846-19-7)

Guidance literature:

With hydrogenchloride; In Isopropyl acetate; water; at 20 ℃;

upstream raw materials:

2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile

3-methoxybenzyl alcohol

(2-allyl-3-methoxyphenyl)methanol

3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol

Downstream raw materials:

2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester

C₃₇H₅₇NO₇S

2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester

Refernces

• 1、 García-Lacuna, Jorge,Domínguez, Gema,Blanco-Urgoiti, Jaime,Pérez-Castells, Javier. "Synthesis of treprostinil: Key claisen rearrangement and catalytic pauson-khand reactions in continuous flow". . p. 9489 - 9501. Retrieved 2019/11/14.
• 2、 -. "Synthesis method of treprostinil". . . Retrieved 2018/03/28.