Treprostinil sodiumProduct ingredient for Treprostinil
- Name
- Treprostinil sodium
- Drug Entry
- Treprostinil
Treprostinil is a stable tricyclic analogue of prostacyclin3 that promotes the vasodilation of pulmonary and systemic arterial vascular beds and the inhibition of platelet aggregation.5,6,7 It reduces symptoms in patients with pulmonary arterial hypertension (PAH) and pulmonary hypertension associated with interstitial lung disease.5,6 The first agent approved for the treatment of PAH was epoprostenol, a synthetic prostacyclin that significantly increases patients' quality of life. However, the use of epoprostenol is limited due to its short half-life (3-5 min) and instability at room temperature.3,4 The use of more stable alternatives such as treprostinil provides patients with PAH with more treatment options.
Treprostinil was approved by the FDA in 2002 for the treatment of pulmonary arterial hypertension.6 It is available in the following routes of administration: subcutaneous, intravenous, inhaled and oral. The first generic form of treprostinil became available in 2019.4
- Accession Number
- DBSALT002321
- Structure
Structure for Treprostinil sodium (DBSALT002321)
- Synonyms
- Not Available
- UNII
- 7JZ75N2NT6
- CAS Number
- 289480-64-4
- Weight
- Average: 412.502
Monoisotopic: 412.22256844 - Chemical Formula
- C23H33NaO5
- InChI Key
- IQKAWAUTOKVMLE-ZSESPEEFSA-M
- InChI
- InChI=1S/C23H34O5.Na/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25;/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27);/q;+1/p-1/t16-,17-,18+,19-,21+;/m0./s1
- IUPAC Name
- sodium 2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetate
- SMILES
- [Na+].CCCCC[C@H](O)CC[C@H]1[C@H](O)C[C@@H]2CC3=C(OCC([O-])=O)C=CC=C3C[C@H]12
- External Links
- ChemSpider
- 5293352
- ChEBI
- 50863
- Wikipedia
- Treprostinil
- Predicted Properties
Property Value Source Water Solubility 0.006 mg/mL ALOGPS logP 3.92 ALOGPS logP 4 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.76 Chemaxon pKa (Strongest Basic) -1.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 89.82 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 118.84 m3·mol-1 Chemaxon Polarizability 44.92 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon