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Key Documents

SML1531

Sigma-Aldrich

Treprostinil

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C23H34O5
Numéro CAS:
Poids moléculaire :
390.51
Numéro MDL:
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

[α]/D 40 to 50°, c = 0.5 in methanol

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

[H][C@@]12[C@@](C[C@@H](O)[C@@H]2CC[C@@H](O)CCCCC)([H])CC3=C(OCC(O)=O)C=CC=C3C1

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+;/m1./s1

Clé InChI

IQKAWAUTOKVMLE-DQHZMXPSSA-M

Actions biochimiques/physiologiques

Treprostinil elicits a longer half-life when compared with iloprost. It mediates inhibition of transforming growth factor-β (TGF-β) and nuclear factor-κB (NF-κB) signaling pathways. Treprostinil effectively reduces right ventricular systolic pressure and inhibits the recruitment of circulating fibrocyte.
Treprostinil is a stable synthetic analog of prostacyclin (prostaglandin PGI2), an IP receptor agonist used clinically for the treatment of pulmonary arterial hypertension. It is a potent vasodilator with antithrombotic, antiproliferative and anti-inflammatory properties.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Robert Roscigno et al.
Pulmonary circulation, 10(4), 2045894020971509-2045894020971509 (2020-12-08)
A dry-powder inhaled formulation of treprostinil (LIQ861) produced using PRINT® technology offers a substantial advantage over current nebulized therapy. Treprostinil is a synthetic prostacyclin analogue that is currently approved for inhalation administration to patients with pulmonary arterial hypertension via nebulized
Aaron Waxman et al.
The New England journal of medicine, 384(4), 325-334 (2021-01-14)
No therapies are currently approved for the treatment of pulmonary hypertension in patients with interstitial lung disease. The safety and efficacy of inhaled treprostinil for patients with this condition are unclear. We enrolled patients with interstitial lung disease and pulmonary
Ming-Kai Tsai et al.
Journal of investigative medicine : the official publication of the American Federation for Clinical Research, 62(2), 332-339 (2014-01-10)
Inflammation plays critical roles in atherosclerosis. Chemokines are responsible for leukocyte trafficking and involve in inflammatory diseases. Macrophage inflammatory protein 1α (MIP-1α) has been implicated in atherosclerotic lesion formation. Prostaglandin I2 (PGI2) analog, used in pulmonary hypertension, has been reported
R James White et al.
American journal of respiratory and critical care medicine, 201(6), 707-717 (2019-11-26)
Rationale: Oral treprostinil improves exercise capacity in patients with pulmonary arterial hypertension (PAH), but the effect on clinical outcomes was unknown.Objectives: To evaluate the effect of oral treprostinil compared with placebo on time to first adjudicated clinical worsening event in
Alessio Coi et al.
Orphanet journal of rare diseases, 16(1), 90-90 (2021-02-19)
Systemic Sclerosis (SSc) is a chronic autoimmune disease with a complex pathogenesis that includes vascular injury, abnormal immune activation, and tissue fibrosis. We provided a complete epidemiological characterization of SSc in the Tuscany region (Italy), considering prevalence and incidence, survival

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