Treprostinil

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Cat Number

API81846197

CAS Number

81846-19-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

81846-19-7

EINECS

808-233-7

Storage

Store at 2-8°C

Synonyms

Uniprost; Rumodolin; Tyvaso; LRX-15; UT-15; treprostinilo; 15AU81; treprostinilum

Molecular Formula

C23H34O5

Molecular Weight

390.5

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

Appearance

White to yellow oily liquid or solid

Melting Point

121-123°C

Boiling Point

587.1±50.0°C (Predicted)

Relative Density

1.158±0.06 (Predicted)

General Description

Treprostinil is a synthetic prostacyclin (PGI2) analogue with a tricyclic benzindene core, structurally distinct from epoprostenol. Its chemical structure is (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-5-carboxylic acid. Treprostinil is a white to off-white powder with a molecular weight of 390.5 Da and is formulated as the sodium salt for stability.

Mechanism of Action

Treprostinil activates the prostacyclin (IP) receptor on vascular smooth muscle cells, increasing intracellular cyclic AMP, leading to potent vasodilation of the pulmonary and systemic arterial beds. This reduces pulmonary arterial pressure and vascular resistance, improving cardiac output. The drug also inhibits platelet aggregation and has antiproliferative effects on vascular smooth muscle, preventing vascular remodeling.

Application

Treprostinil is indicated for the treatment of pulmonary arterial hypertension (PAH) to improve exercise capacity and delay clinical worsening. It is used in patients with WHO functional class II-IV symptoms and is available in multiple routes, including intravenous, subcutaneous, inhaled, and oral. The drug is also used for the treatment of chronic thromboembolic pulmonary hypertension (CTEPH) and for Raynaud's phenomenon.

Oral treprostinil, the only FDA-approved oral prostacyclin for pulmonary arterial hypertension, improves exercise tolerance in treatment-naïve patients but not those on background oral therapy. Higher doses are more efficacious but complicated by side effects and dosing complexity. While its therapeutic role remains unclear, ongoing studies may clarify its position in PAH treatment.

Fig. 1 Mean concentration–time profiles of treprostinil diolamine (UT-15C): 2 and 6 mg. (Pugliese SC, Bull TM, 2016)

References

Pugliese SC, Bull TM. Clinical use of extended-release oral treprostinil in the treatment of pulmonary arterial hypertension. Integr Blood Press Control. 2016;9:1-7.

Does Treprostinil require protection from light and heat during storage?

Yes, it is sensitive to both light and heat. Light causes photodegradation and heat accelerates oxidation of the prostacyclin ring. Store in light-resistant containers at 2-8°C.

Is Treprostinil stable in solution for subcutaneous or intravenous infusion?

Formulated solutions are stable at room temperature for up to 24 hours when protected from light.

What is the recommended packaging for Treprostinil to prevent degradation?

Use amber glass vials with PTFE-lined caps, sealed under nitrogen. Store in refrigerated conditions and protect from light during handling.

How is the impurity treprostinil 15-keto (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method with UV detection, ensuring it remains within ICH limits.