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Treprostinil is a stable analog of prostacyclin (sc-201231). Treprostinil is used clinically for the treatment of primary pulmonary hypertension (PPH). PPH is characterized by increasing pulmonary arterial and vascular resistance, and the cause is unknown. The structural modifications in treprostinil compared to prostacyclin increase the plasma half-life from 2 minutes to 34 and 85 minutes for intravenous and subcutaneous infusion of the drug, respectively. In addition to treprostinils direct vasodilatory effects, it also inhibits inflammatory cytokine (TNFα, IL-1β, IL-6, GM-CF) production by human alveolar macrophages in the sub-micromolar range by preventing NF-κB translocation to the nucleus.
Treprostinil is a potent prostacyclin (PGI2) analog (EC50 values are 0.6, 1.9 and 6.2 nM at DP1, IP and EP2 receptors respectively). Causes vasodilation of human pulmonary arteries and inhibits NFκB nuclear translocation in human alveolar macrophages in vitro.
Treprostinil is rapidly absorbed from the subcutaneous site of infusion, with an almost 100% bioavailability and a mean half-life of 85 minutes (34 minutes for the IV infusion). The IV solution must be diluted with normal saline or sterile water before starting the infusion. Unlike epoprostenol, treprostinil is stable at room temperature for up to 5 years, with vasodilation action lasting from 4 to 6 hours, compared with the short, 2- to 3-minute action for epoprostenol. Because of its long life in the body, it can be administered under the skin with a microinfusion subcutaneous infusion pump rather than into the bloodstream and, thus, without hospitalization, as contrasted with the central IV infusion of epoprostenol.
Formal Name
2-
CAS Number
81846-19-7
Synonyms
Molecular Formula
C23H34O5
Formula Weight
390.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
λmax
206, 218, 277 nm
SMILES
O=C(O)COC1=C(C[C@](C[C@@H](O)[C@@H]2CC[C@@H](O)CCCCC)([H])[C@]2([H])C3)C3=CC=C1
InChi Code
InChI=1S/C23H34O5/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)/t16-,17-,18+,19-,21+/m0/s1
InChi Key
PAJMKGZZBBTTOY-ZFORQUDYSA-N
Storage
-20°C
Shipping
Room Temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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