A potent, stable prostacyclin analog
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Treprostinil

Item No. 10162

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(1R,2R,3aS,9aS)-2,3,4,9,9a-hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]oxy]-acetic acid
CAS Number
81846-19-7
Synonyms
  • BW 15AU
  • LRX 15
  • Rumodolin
  • U-62840
  • Uniprost
Molecular Formula
C23H34O5
Formula Weight
390.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $107

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    5 mg

    $477

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    10 mg

    $845

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    Product Description

    Primary pulmonary hypertension (PPH) is a condition of unknown cause that is characterized by increasing pulmonary arterial and vascular resistance. Treprostinil is a stable analog of prostacyclin (Item No. 18220) that is used clinically for the treatment of PPH under the trade name Remodulin™. 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.1 In addition to treprostinil’s 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.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Olschewski, H., Rose, F., Schermuly, R., et al. Prostacyclin and its analogues in the treatment of pulmonary hypertension. Pharmacol. Ther. 102(2), 139-153 (2004).

    2. Raychauduri, B., Malur, A., Bonfield, T.L., et al. The prostacyclin analogue treprostinil blocks NFκB nuclear translocation in human alveolar macrophages. The Journal of Biological Chemisty 277(36), 33344-33348 (2002).

    Product Citations

    Fuchikami, C., Murakami, K., Tajima, K., et al. A comparison of vasodilation mode among selexipag (NS-304; [2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide]), its active metabolite MRE-269 and various prostacyclin receptor agonists in rat, porcine and human pulmonary arteries. Eur. J. Pharmacol. 795, 75-83 (2017).