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Merck
CN

SML1531

Treprostinil

≥98% (HPLC), prostacyclin receptor agonist, powder

Synonym(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

Empirical Formula (Hill Notation):
C23H34O5
CAS Number:
81846-19-7
Molecular Weight:
390.51
NACRES:
NA.77
UNSPSC Code:
12352200
MDL number:
MFCD00888847

Key Documents

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Product Name

Treprostinil, ≥98% (HPLC)

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

SMILES string

[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 key

IQKAWAUTOKVMLE-DQHZMXPSSA-M

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D 40 to 50°, c = 0.5 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Synthetic analog of prostacyclin (prostaglandin PGI2); vasodilator used for the treatment of pulmonary arterial hypertension
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H319

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Certificates of Analysis (COA)

Lot/Batch Number
0000525265
0000525264
0000525264
0000525265
0000468825

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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
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
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
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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