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SML1531

Treprostinil

Name: Treprostinil
Brand: SIGMA

≥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

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Treprostinil, ≥98% (HPLC)

Quality Level

100

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

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

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

InChI key

IQKAWAUTOKVMLE-DQHZMXPSSA-M

Related Categories

Bioactive Small Molecules

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

GHS07

signalword

Warning

hcodes

H302,H319

pcodes

P264 - P280 - P301 + P312 - P305 + P351 + P338 - P337 + P313 - P501

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Treatment With Treprostinil and Metformin Normalizes Hyperglycemia and Improves Cardiac Function in Pulmonary Hypertension Associated With Heart Failure With Preserved Ejection Fraction.

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

Ambulatory Transition from Parenteral Prostanoid to Inhaled Treprostinil in Patients with Pulmonary Arterial Hypertension.

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

Effect of prostaglandin I2 analogs on macrophage inflammatory protein 1α in human monocytes via I prostanoid receptor and cyclic adenosine monophosphate.

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

Pharmacokinetics and tolerability of LIQ861, a novel dry-powder formulation of treprostinil.

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

Epidemiology of systemic sclerosis: a multi-database population-based study in Tuscany (Italy).

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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Global Trade Item Number

SKU	GTIN
SML1531-5MG	04061832787220
SML1531-25MG	04061832787213

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