treprostinil

Also known as LRX-15, ({(1R,2R,3aS,9aS)-2-Hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphtalen-5-yl}oxy)acetic acid, (1R,2R,3aS,9aS)-({2,3,3a,4,9,9a-hexahydro-2-hydroxy- 1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl}oxy)acetic acid

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.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 477864833
Drug.image: Treprostinil.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Treprostinil2.png
Drug.image_class2: bg-transparent
Drug.tradename: Remodulin, Orenitram, Tyvaso, others
Drug.MedlinePlus: a622038
Drug.DailyMedID: Treprostinil
Drug.pregnancy_AU: B3
Drug.routes_of_administration: Subcutaneous, intravenous, inhalation, by mouth
Drug.ATC_prefix: B01
Drug.ATC_suffix: AC21
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only
Drug.legal_status: Rx-only

via Wikipedia infobox

Chemical data

Formula: C23H34O5
Molecular weight: 390.5 g/mol
IUPAC name: 2-[[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[g]naphthalen-5-yl]oxy]acetic acid
SMILES: CCCCC[C@@H](CC[C@H]1[C@@H](C[C@H]2[C@@H]1CC3=C(C2)C(=CC=C3)OCC(=O)O)O)O
InChIKey: PAJMKGZZBBTTOY-ZFORQUDYSA-N
XLogP: 4.5
Polar surface area: 87 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2002
Admin. routes: oral, parenteral, topical
Indications: ischemia reperfusion injury, pulmonary arterial hypertension, chronic obstructive pulmonary disease, systemic scleroderma

via ChEMBL · EBI

Research

987 papers

Inhaled Treprostinil in Pulmonary Hypertension Due to Interstitial Lung Disease.The New England journal of medicine · 2021
Treprostinil Use in the NICU.Advances in neonatal care : official journal of the National Association of Neonatal Nurses · 2024
Inhaled treprostinil and forced vital capacity in patients with interstitial lung disease and associated pulmonary hypertension: a post-hoc analysis of the INCREASE study.The Lancet. Respiratory medicine · 2021
Long-term inhaled treprostinil for pulmonary hypertension due to interstitial lung disease: INCREASE open-label extension study.The European respiratory journal · 2023
Addition of inhaled treprostinil to oral therapy for pulmonary arterial hypertension: a randomized controlled clinical trial.Journal of the American College of Cardiology · 2010

via PubMed

Wikidata facts

Mass: 390.241
Has use: medication

Show 7 more facts

chemical formula: C₂₃H₃₄O₅
subject has role: antihypertensive drug
isomeric SMILES: CCCCC[C@@H](CC[C@H]1[C@@H](C[C@H]2[C@@H]1CC3=C(C2)C(=CC=C3)OCC(=O)O)O)O
canonical SMILES: CCCCCC(CCC1C(CC2C1CC3=C(C2)C(=CC=C3)OCC(=O)O)O)O
World Health Organisation international non-proprietary name: treprostinil
defined daily dose: 4.3
physically interacts with: Prostaglandin I2 receptor

Sources (4)

via Wikidata · CC0

~3 min read

Encyclopedic overview

7 sections

Contents

Medical uses
Adverse effects
History
Research
References
Further reading
External links

Treprostinil was approved for use in the United States in May 2002.

Excerpted from Wikipedia’s “treprostinil” article, available under the CC BY-SA 4.0 licence.

Available in 16 languages

via Wikidata sitelinks · CC0