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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:
81846-19-7
Poids moléculaire :
390.51
Numéro MDL:
MFCD00888847
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

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
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
Longfei Wang et al.
Arteriosclerosis, thrombosis, and vascular biology, 40(6), 1543-1558 (2020-04-10)
Pulmonary hypertension (PH) due to left heart disease (group 2), especially in the setting of heart failure with preserved ejection fraction (HFpEF), is the most common cause of PH worldwide; however, at present, there is no proven effective therapy available
Lucas M Kimmig et al.
Lung, 198(1), 53-58 (2020-01-09)
The intravenous or subcutaneous delivery of prostanoid drugs for moderate to severe pulmonary arterial hypertension has been fraught with complications and patient dissatisfaction. Combination therapy including inhaled treprostinil is an attractive alternative in clinically stable patients. Uncertainties exist about the
Gulsev Ozen et al.
British journal of pharmacology, 177(1), 161-174 (2019-09-03)
In patients with pulmonary hypertension (PH) associated with lung disease and/or hypoxia (Group III), decreased pulmonary vascular tone and tissue hypoxia is therapeutically beneficial. PGE2 and PGI2 induce potent relaxation of human bronchi from non-PH (control) patients via EP4 and
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