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Treprostinil
Chemical compound
Chemical compound
| Field | Value | ||
|---|---|---|---|
| Verifiedfields | changed | ||
| Watchedfields | changed | ||
| verifiedrevid | 477864833 | ||
| image | Treprostinil.svg | ||
| image_class | skin-invert-image | ||
| width | 250 | ||
| image2 | Treprostinil2.png | ||
| image_class2 | bg-transparent | ||
| tradename | Remodulin, Orenitram, Tyvaso, others | ||
| Drugs.com | |||
| MedlinePlus | a622038 | ||
| DailyMedID | Treprostinil | ||
| pregnancy_AU | B3 | ||
| routes_of_administration | Subcutaneous, intravenous, inhalation, by mouth | ||
| ATC_prefix | B01 | ||
| ATC_suffix | AC21 | ||
| legal_AU | |||
| legal_BR | |||
| legal_CA | |||
| legal_DE | |||
| legal_NZ | |||
| legal_UK | |||
| legal_US | Rx-only | ||
| legal_US_comment | |||
| legal_EU | Rx-only | ||
| legal_EU_comment | |||
| legal_UN | |||
| legal_status | Rx-only | ||
| bioavailability | ~100% | ||
| metabolism | Substantially metabolized by the liver | ||
| elimination_half-life | 4 hours | ||
| excretion | Urine (79% of administered dose is excreted as 4% unchanged drug and 64% as identified metabolites); feces (13%) | ||
| CAS_number_Ref | |||
| CAS_number | 81846-19-7 | ||
| PubChem | 6918140 | ||
| IUPHAR_ligand | 5820 | ||
| DrugBank_Ref | |||
| DrugBank | DB00374 | ||
| ChemSpiderID_Ref | |||
| ChemSpiderID | 5293353 | ||
| UNII_Ref | |||
| UNII | RUM6K67ESG | ||
| KEGG_Ref | |||
| KEGG | D06213 | ||
| KEGG2_Ref | |||
| KEGG2 | D08628 | ||
| ChEBI_Ref | |||
| ChEBI | 50861 | ||
| ChEMBL_Ref | |||
| ChEMBL | 1201254 | ||
| IUPAC_name | (1*R*,2*R*,3a*S*,9a*S*)-[[2,3,3a,4,9,9a-Hexahydro-2-hydroxy-1-[(3*S*)-3-hydroxyoctyl]-1*H*-benz[f]inden-5-yl]oxy]acetic acid | ||
| C | 23 | H=34 | O=5 |
| StdInChI_Ref | |||
| StdInChI | 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 | ||
| StdInChIKey_Ref | |||
| StdInChIKey | PAJMKGZZBBTTOY-ZFORQUDYSA-N |
| Drugs.com =
| elimination_half-life = 4 hours
Treprostinil, sold under the brand names Remodulin for infusion, Orenitram for oral, and Tyvaso for inhalation among others, is a vasodilator that is used for the treatment of pulmonary arterial hypertension.
Treprostinil was approved for use in the United States in May 2002.
Medical uses
Treprostinil is indicated for the treatment of pulmonary arterial hypertension in people with NYHA Class II-IV symptoms to diminish symptoms associated with exercise.
Treprostinil inhalation solution and treprostinil inhalation powder are indicated for the treatment of people with pulmonary arterial hypertension (WHO Group 1) to improve exercise ability; and people with pulmonary hypertension associated with interstitial lung disease (WHO Group 3) to improve exercise ability.
In the European Union, treprostinil (Trepulmix) is indicated for the treatment of adults with WHO Functional Class III or IV and inoperable chronic thromboembolic pulmonary hypertension; or persistent or recurrent chronic thromboembolic pulmonary hypertension after surgical treatment to improve exercise capacity.
Adverse effects
- Since treprostinil is a vasodilator, its antihypertensive effect may be compounded by other medications that affect the blood pressure, including calcium channel blockers, diuretics, and other vasodilating agents.
- Because of treprostinil's inhibiting effect on platelet aggregation, there is an increased risk of bleeding, especially among patients who are also taking anticoagulants.
Common side effects depending on route of administration:
- 85% of patients report pain or other reaction at the infusion site.
History
Main article: Prostacyclin#History
In 1976, the first paper on prostacyclin was published.
Treprostinil (Remodulin) was approved for medical use in the United States in May 2002, and again in July 2018.
Treprostinil (Tyvaso), as inhalation solution, was approved for medical use in the United States in July 2009, and again in April 2021.
Treprostinil (Orenitram), as extended release tablets, was approved for medical use in the United States in December 2013.
Treprostinil (Trepulmix) was authorized for medical use in the European Union in April 2020. Trepulmix is a hybrid medicine that is similar to the reference medicine Remodulin. It contains the same active substance, but it is used for treating a different form of pulmonary hypertension.
Treprostinil (Tyvaso DPI), as inhalation powder, was approved for medical use in the United States in May 2022.
Treprostinil (Yutrepia), as inhalation powder, was approved for medical use in the United States in June 2025.
Research
Treprostinil therapy may be effective in treating Degos disease.
References
References
- (9 October 2023). "Remodulin- treprostinil injection, solution; Sterile diluent for remodulin- water injection, solution".
- (7 November 2023). "Orenitram- treprostinil tablet, extended release; Orenitram- treprostinil kit".
- (8 December 2023). "Tyvaso- treprostinil inhalant".
- (26 January 2024). "Tyvaso DPI- treprostinil inhalant; Tyvaso DPI- treprostinil kit".
- (2 June 2025). "Yutrepia- treprostinil capsule".
- (January 2013). "Treprostinil for the treatment of pulmonary arterial hypertension". Expert Review of Cardiovascular Therapy.
- (31 July 2002). "Drug Approval Package: Remodulin (Treprostinil Sodium) NDA #021272".
- (December 2016). "A Comprehensive Review of Treprostinil Pharmacokinetics via Four Routes of Administration". Clinical Pharmacokinetics.
- (October 1976). "An enzyme isolated from arteries transforms prostaglandin endoperoxides to an unstable substance that inhibits platelet aggregation". Nature.
- (7 February 2019). "Drug Approval Package: Remodulin".
- (27 September 2017). "Drug Approval Package: Tyvaso (Treprostinil) Inhalation Solution NDA #022387".
- (1 April 2021). "United Therapeutics Announces FDA Approval and Launch of Tyvaso for the Treatment of Pulmonary Hypertension Associated with Interstitial Lung Disease". United Therapeutics.
- (23 July 2014). "Drug Approval Package: Orenitram (Treprostinil) Extended Release Tablets NDA #203496".
- (29 January 2020). "Trepulmix EPAR".
- (6 July 2022). "Drug Approval Package: Tyvaso DPI".
- (24 May 2022). "United Therapeutics Announces FDA Approval of Tyvaso DPI". United Therapeutics.
- (2025-05-23). "Letter to Kristan Amicone about NDA Approval for Yutrepia".
- (23 May 2025). "U.S. FDA Approves Liquidia's Yutrepia (treprostinil) Inhalation Powder for Patients with Pulmonary Arterial Hypertension (PAH) and Pulmonary Hypertension Associated with Interstitial Lung Disease (PH-ILD)". Liquidia Technologies.
- (April 2013). "Effective treatment of malignant atrophic papulosis (Köhlmeier-Degos disease) with treprostinil--early experience". Orphanet Journal of Rare Diseases.
This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.
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