Treprostinil diolamineProduct ingredient for Treprostinil

Name
Treprostinil diolamine
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
DBSALT001333
Structure
Synonyms
Not Available
UNII
H1FKG90039
CAS Number
830354-48-8
Weight
Average: 495.657
Monoisotopic: 495.319602793
Chemical Formula
C27H45NO7
InChI Key
RHWRWEUCEXUUAV-ZSESPEEFSA-N
InChI
InChI=1S/C23H34O5.C4H11NO2/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;6-3-1-5-2-4-7/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27);5-7H,1-4H2/t16-,17-,18+,19-,21+;/m0./s1
IUPAC Name
2-[(2-hydroxyethyl)amino]ethan-1-ol; 2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid
SMILES
OCCNCCO.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
ChemSpider
9354549
ChEMBL
CHEMBL2107815
Predicted Properties
PropertyValueSource
Water Solubility0.00731 mg/mLALOGPS
logP3.53ALOGPS
logP4Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.76Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.99 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity108 m3·mol-1Chemaxon
Polarizability45.43 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon