Treprostinil free acid
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MedKoo CAT#: 318899

CAS#: 81846-19-7 (free acid)

Description: Treprostinil is a vasodilator that is used for the treatment of pulmonary arterial hypertension. Treprostinil is a chemically stable prostacyclin analog. Its principal pharmacologic action is direct vasodilation, which causes reduction of pulmonary and systemic arterial pressure, reducing right and left ventricular afterload; therefore improves the cardiac output. It also has an antiplatelet effect.

Chemical Structure

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Treprostinil free acid
CAS# 81846-19-7 (free acid)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318899
Name: Treprostinil free acid
CAS#: 81846-19-7 (free acid)
Chemical Formula: C23H34O5
Exact Mass: 390.24
Molecular Weight: 390.520
Elemental Analysis: C, 70.74; H, 8.78; O, 20.48

Price and Availability

Size Price Availability Quantity
5mg USD 90 Ready to ship
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1350 Ready to ship
500mg USD 2650 Ready to ship
1g USD 4250 Ready to ship
2g USD 6950 Ready to ship
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Related CAS #: 289480-64-4 (sodium)   81846-19-7 (free acid)   830354-48-8 (diolamine)    

Synonym: UT-15; UT 15; UT15; LRX 15; LRX-15; LRX15; BW 15AU; U-62840; Uniprost; Treprostinil; Orenitram; Remodulin.

IUPAC/Chemical Name: 2-(((1R,2R,3aS,9aS)-2-hydroxy-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yl)oxy)acetic acid

InChi Key: PAJMKGZZBBTTOY-ZFORQUDYSA-N

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

SMILES Code: O=C(O)COC1=C2C[C@@]3([H])C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]3([H])CC2=CC=C1

Appearance: Oily liquid

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Treprostinil (LRX-15) is a potent DP1 and EP2 agonist with EC50 values of 0.6±0.1 and 6.2±1.2 nM, respectively.
In vitro activity: The effect of Treprostinil on TGF-ß1 and PDGF-induced fibroblast proliferation and ECM deposition was investigated. Human peripheral lung fibroblasts of seven IPF patients and five lung donors were stimulated by PDGF, or TGF-β1, or the combination. Cells were pre-incubated (30 min) with either Treprostinil, forskolin, di-deoxyadenosine (DDA), or vehicle. Treprostinil time dependently activated cAMP thereby preventing PDGF-BB induced proliferation and TGF-β1 secretion. Cell counts indicated proliferation; αsmooth muscle actin (α-SMA) indicted differentiation, and collagen type-1 or fibronectin deposition remodeling. Myo-fibroblast indicating α-SMA expression was significantly reduced and its formation was altered by Treprostinil. Collagen type-I and fibronectin deposition were also reduced by Treprostinil. The effect of Treprostinil on collagen type-I deposition was cAMP sensitive as it was counteracted by DDA, while the effect on fibronectin was not cAMP mediated. Treprostinil antagonized the pro-fibrotic effects of both PDGF-BB and TGF-β1 in primary human lung fibroblasts. The data presented propose a therapeutic relevant anti-fibrotic effect of Treprostinil in IPF (idiopathic pulmonary fibrosis). Reference: Sci Rep. 2018 Jan 18;8(1):1087. https://pubmed.ncbi.nlm.nih.gov/29348469/
In vivo activity: To evaluate the preventative effect of treprostinil on metabolic syndrome-associated PH-HFpEF, treprostinil (40 ng/kg/min, the effective dose for PAH therapy with similar average infusion rate achieved in clinical trials, on a ng/m2 basis) was given through osmotic minipumps for 16 weeks in mice fed with a HFD (Figure 1A), which has been shown to induce PH and/or HFpEF phenotype in mice. Consistent with previous studies, HFD-exposed mice had significantly higher body weights, hyperglycemia and glucose intolerance when compared to RD-treated mice (Figure 1B through 1D). Additionally, HFD-exposed mice developed mild PH and/or HFpEF phenotype as evidenced by elevated right ventricular systolic pressure (RVSP), higher left ventricular end diastolic pressure (LVEDP), preserved left ventricular ejection fraction (LVEF) and both LV and RV hypertrophy (Figure 1E through 1I). In contrast, chronic treprostinil treatment significantly lowered HbA1c levels and improved glucose intolerance independent of changes in body weight (Figure 1B through 1D). Furthermore, a tendency for treprostinil to lower pulmonary pressures was observed in HFD-exposed mice (P = 0.058; Figure 1E), although treprostinil caused no significant differences in LVEDP and biventricular hypertrophy (Figure 1F,1H and 1I). Collectively, these data demonstrate that chronic treprostinil treatment improves glucose metabolism and lowers pulmonary hypertension in a mild mouse model of PH-HFpEF induced by HFD. Reference: Arterioscler Thromb Vasc Biol. 2020 Jun;40(6):1543-1558. https://pubmed.ncbi.nlm.nih.gov/32268788/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 125.0 320.09

Preparing Stock Solutions

The following data is based on the product molecular weight 390.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Nikam VS, Schermuly RT, Dumitrascu R, Weissmann N, Kwapiszewska G, Morrell N, Klepetko W, Fink L, Seeger W, Voswinckel R. Treprostinil inhibits the recruitment of bone marrow-derived circulating fibrocytes in chronic hypoxic pulmonary hypertension. Eur Respir J. 2010 Dec;36(6):1302-14. doi: 10.1183/09031936.00028009. Epub 2010 Jun 4. PMID: 20525716. 2. Wang L, Halliday G, Huot JR, Satoh T, Baust JJ, Fisher A, Cook T, Hu J, Avolio T, Goncharov DA, Bai Y, Vanderpool RR, Considine RV, Bonetto A, Tan J, Bachman TN, Sebastiani A, McTiernan CF, Mora AL, Machado RF, Goncharova EA, Gladwin MT, Lai YC. Treatment With Treprostinil and Metformin Normalizes Hyperglycemia and Improves Cardiac Function in Pulmonary Hypertension Associated With Heart Failure With Preserved Ejection Fraction. Arterioscler Thromb Vasc Biol. 2020 Jun;40(6):15431558. doi: 10.1161/ATVBAHA.119.313883. Epub 2020 Apr 9. PMID: 32268788; PMCID: PMC7255946. 3. Themanns M, Koban F, Bergmayr C, Chrzan A, Strohmaier W, Haybaeck J, Freissmuth M, Zebedin-Brandl E. Treprostinil reduces endothelial damage in murine sinusoidal obstruction syndrome. J Mol Med (Berl). 2019 Feb;97(2):201-213. doi: 10.1007/s00109-0181726-6. Epub 2018 Dec 7. PMID: 30535954; PMCID: PMC6348071. 4. Lambers C, Roth M, Jaksch P, Muraközy G, Tamm M, Klepetko W, Ghanim B, Zhao F. Treprostinil inhibits proliferation and extracellular matrix deposition by fibroblasts through cAMP activation. Sci Rep. 2018 Jan 18;8(1):1087. doi: 10.1038/s41598-01819294-1. PMID: 29348469; PMCID: PMC5773699.
In vitro protocol: 1. Themanns M, Koban F, Bergmayr C, Chrzan A, Strohmaier W, Haybaeck J, Freissmuth M, Zebedin-Brandl E. Treprostinil reduces endothelial damage in murine sinusoidal obstruction syndrome. J Mol Med (Berl). 2019 Feb;97(2):201-213. doi: 10.1007/s00109-0181726-6. Epub 2018 Dec 7. PMID: 30535954; PMCID: PMC6348071. 2. Lambers C, Roth M, Jaksch P, Muraközy G, Tamm M, Klepetko W, Ghanim B, Zhao F. Treprostinil inhibits proliferation and extracellular matrix deposition by fibroblasts through cAMP activation. Sci Rep. 2018 Jan 18;8(1):1087. doi: 10.1038/s41598-01819294-1. PMID: 29348469; PMCID: PMC5773699.
In vivo protocol: 1. Nikam VS, Schermuly RT, Dumitrascu R, Weissmann N, Kwapiszewska G, Morrell N, Klepetko W, Fink L, Seeger W, Voswinckel R. Treprostinil inhibits the recruitment of bone marrow-derived circulating fibrocytes in chronic hypoxic pulmonary hypertension. Eur Respir J. 2010 Dec;36(6):1302-14. doi: 10.1183/09031936.00028009. Epub 2010 Jun 4. PMID: 20525716. 2. Wang L, Halliday G, Huot JR, Satoh T, Baust JJ, Fisher A, Cook T, Hu J, Avolio T, Goncharov DA, Bai Y, Vanderpool RR, Considine RV, Bonetto A, Tan J, Bachman TN, Sebastiani A, McTiernan CF, Mora AL, Machado RF, Goncharova EA, Gladwin MT, Lai YC. Treatment With Treprostinil and Metformin Normalizes Hyperglycemia and Improves Cardiac Function in Pulmonary Hypertension Associated With Heart Failure With Preserved Ejection Fraction. Arterioscler Thromb Vasc Biol. 2020 Jun;40(6):15431558. doi: 10.1161/ATVBAHA.119.313883. Epub 2020 Apr 9. PMID: 32268788; PMCID: PMC7255946.

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1: Fang L, Chen WC, Jaksch P, Molino A, Saglia A, Roth M, Lambers C. Treprostinil Reconstitutes Mitochondrial Organisation and Structure in Idiopathic Pulmonary Fibrosis Cells. Int J Mol Sci. 2023 Jul 29;24(15):12148. doi: 10.3390/ijms241512148. PMID: 37569523; PMCID: PMC10418929.


2: Parikh R, O'Sullivan DM, Farber HW. The PH-ILD Detection tool: External validation and use in patients with ILD. Pulm Circ. 2023 Aug 8;13(3):e12273. doi: 10.1002/pul2.12273. PMID: 37564922; PMCID: PMC10410234.


3: Schramm JE, Dykes JC, Hopper RK, Feinstein JA, Rosenthal DN, Kameny RJ. Pulmonary Vasodilator Therapy in Pediatric Patients on Ventricular Assist Device Support: A Single-Center Experience and Proposal for Use. ASAIO J. 2023 Aug 9. doi: 10.1097/MAT.0000000000002023. Epub ahead of print. PMID: 37556563.


4: Harutyunova S, Benjamin N, Eichstaedt C, Marra AM, Xanthouli P, Nagel C, Grünig E, Egenlauf B. Long-Term Safety, Outcome, and Clinical Effects of Subcutaneous and Intravenous Treprostinil Treatment in Patients with Severe Chronic Pulmonary Arterial Hypertension. Respiration. 2023 Aug 4:1-12. doi: 10.1159/000531169. Epub ahead of print. PMID: 37544296.


5: Miller CE, Franco V, Smith JS, Balasubramanian V, Kingrey J, Zolty R, Melendres-Groves L, Huston J, Elwing JM, Ravichandran A, Cella D, Shen E, Seaman S, Thrasher CM, Broderick M, Oudiz RJ. Parenteral treprostinil induction for rapid attainment of therapeutic doses of oral treprostinil. Respir Med. 2023 Aug 1;218:107374. doi: 10.1016/j.rmed.2023.107374. Epub ahead of print. PMID: 37532157.


6: Miyanaga S, Kubota K, Iwatani N, Akao M, Mitsuyoshi K, Ohishi M. Pulmonary artery hypertension-associated with human immunodeficiency virus infection with attenuated effect of subcutaneous treprostinil injection during long-term observation: A case report. J Cardiol Cases. 2023 Jun 1;28(2):72-74. doi: 10.1016/j.jccase.2023.04.008. PMID: 37521577; PMCID: PMC10382956.


7: Kingrey JF, Miller CE, Franco V, Smith JS, Zolty R, Oudiz RJ, Elwing JM, Huston JH, Melendres-Groves L, Ravichandran A, Balasubramanian V, Wu B, Hwang S, Seaman S, Broderick M, Rahaghi FF. Implementing the EXPEDITE parenteral induction protocol: Rapid parenteral treprostinil titration and transition to oral treprostinil. Pulm Circ. 2023 Jul 25;13(3):e12255. doi: 10.1002/pul2.12255. PMID: 37497167; PMCID: PMC10368085.


8: Blanco I, Hernández-González F, García A, Torres-Castro R, Barberà JA. Management of Pulmonary Hypertension Associated with Chronic Lung Disease. Semin Respir Crit Care Med. 2023 Jul 24. doi: 10.1055/s-0043-1770121. Epub ahead of print. PMID: 37487524.


9: West N, Smoot K, Patzlaff N, Miceli M, Waxman A. Plain language summary of the INCREASE study: inhaled treprostinil (Tyvaso) for the treatment of pulmonary hypertension due to interstitial lung disease. Future Cardiol. 2023 Apr;19(5):229-239. doi: 10.2217/fca-2022-0108. Epub 2023 Jul 19. PMID: 37466095.


10: Coons JC, Empey PE. Pharmacogenomics in the Management of Pulmonary Arterial Hypertension: Current Perspectives. Pharmgenomics Pers Med. 2023 Jul 11;16:729-737. doi: 10.2147/PGPM.S361222. PMID: 37457231; PMCID: PMC10349598.


11: Lachant D, Minkin R, Swisher J, Mogri M, Zolty R, Hwang S, Seaman S, Broderick M, Sahay S. Safety and efficacy of transitioning from selexipag to oral treprostinil in pulmonary arterial hypertension: Findings from the ADAPT registry. Pulm Pharmacol Ther. 2023 Jul 13;82:102232. doi: 10.1016/j.pupt.2023.102232. Epub ahead of print. PMID: 37451609.


12: Abu-Hanna J, Anastasakis E, Patel JA, Eddama MMR, Denton CP, Taanman JW, Abraham D, Clapp LH. Prostacyclin mimetics inhibit DRP1-mediated pro- proliferative mitochondrial fragmentation in pulmonary arterial hypertension. Vascul Pharmacol. 2023 Aug;151:107194. doi: 10.1016/j.vph.2023.107194. Epub 2023 Jul 11. PMID: 37442283.


13: Carbone RG, Monselise A, Puppo F. Treprostinil and Clinical Outcome in Pulmonary Hypertension and Interstitial Lung Disease: Is All Clear? Chest. 2023 Jul;164(1):e21. doi: 10.1016/j.chest.2023.04.015. PMID: 37423704.


14: Cottin V, Diesler R, Turquier S, Valenzuela C. Interstitial lung disease- associated pulmonary hypertension - what the future holds. Curr Opin Pulm Med. 2023 Sep 1;29(5):406-415. doi: 10.1097/MCP.0000000000000992. Epub 2023 Jul 7. PMID: 37417835.


15: Cottin V, Valenzuela C, Humbert M. Inhaled treprostinil for interstitial lung disease-associated pulmonary hypertension: a silver lining on a very dark cloud. Eur Respir J. 2023 Jun 29;61(6):2300944. doi: 10.1183/13993003.00944-2023. PMID: 37385654.


16: Brewer J, Kimber A. Cannabidiol (CBD) for the treatment of subcutaneous treprostinil (Remodulin®) site pain: a case report. Front Med (Lausanne). 2023 Jun 13;10:1188083. doi: 10.3389/fmed.2023.1188083. PMID: 37384049; PMCID: PMC10293745.


17: Fabyan KD, Chandel A, King CS. Pulmonary Hypertension in Interstitial Lung Disease: Management Options to Move Beyond Supportive Care. Curr Pulmonol Rep. 2023 May 22:1-8. doi: 10.1007/s13665-023-00311-2. Epub ahead of print. PMID: 37362782; PMCID: PMC10200699.


18: Avitabile CM, Flohr S, Mathew L, Wang Y, Ash D, Frank DB, Tingo JE, Rintoul NE, Hedrick HL. Quantitative Measures of Right Ventricular Size and Function by Echocardiogram Correlate with Cardiac Catheterization Hemodynamics in Congenital Diaphragmatic Hernia. J Pediatr. 2023 Jun 15;261:113564. doi: 10.1016/j.jpeds.2023.113564. Epub ahead of print. PMID: 37329980.


19: Ting YH, Yu MW, Wu YJ, Wu SH. Long-Term Experience and Safety of Transitioning from Subcutaneous Treprostinil to Oral Selexipag in the High-Risk Pulmonary Hypertension Patient: A Case Report. Acta Cardiol Sin. 2023 May;39(3):492-496. doi: 10.6515/ACS.202305_39(3).20230130A. PMID: 37229336; PMCID: PMC10203720.


20: Wiedenroth CB, Pruefer D, Adameit MSD, Mayer E, Guth S. Chronic thromboembolic pulmonary hypertension-medical, interventional, and surgical therapy. Herz. 2023 Aug;48(4):280-284. English. doi: 10.1007/s00059-023-05172-8. Epub 2023 Apr 25. PMID: 37186021.