Ifetroban

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Chemical compound

title: "Ifetroban" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["oxazoles", "pentyl-compounds", "experimental-drugs"] description: "Chemical compound" topic_path: "general/oxazoles" source: "https://en.wikipedia.org/wiki/Ifetroban" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = | IUPAC_name = 3-[2-({(1S,2R,3S)-3-[4-(Pentylcarbamoyl)-1,3-oxazol-2-yl]-7-oxabicyclo[2.2.1]hept-2-yl}methyl)phenyl]propanoic acid | image = Ifetroban.svg | image_class = skin-invert-image

| tradename = | pregnancy_category = | legal_status = Investigational | routes_of_administration =

| bioavailability = | metabolism = | excretion =

| CAS_number = 143443-90-7 | ATC_prefix = None | PubChem = 23724921 | DrugBank = DB12321 | ChemSpiderID = 58452 | ChEMBL = 2146062 | UNII_Ref = | UNII = E833KT807K | KEGG = D04500 | synonyms =

| C=25 | H=32 | N=2 | O=5 | smiles = O=C(NCCCCC)c1nc(oc1)[C@@H]4C2OC@@H[C@@H]4Cc3ccccc3CCC(=O)O

Ifetroban is a potent and selective thromboxane receptor antagonist. It has been studied in animal models for the treatment of cancer metastasis, myocardial ischemia, hypertension, stroke, thrombosis, cardiomyopathy, and for its effects on platelets. Clinical trials are evaluating the therapeutic safety and efficacy of oral ifetroban capsules for the treatment of cancer metastasis, cardiovascular disease, aspirin exacerbated respiratory disease, systemic sclerosis, and Duchenne muscular dystrophy.

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/b/b1/Ifetroban_synthesis.png" caption="date=January 2026}}"] ::

References

References

  1. (2006). "Ifetroban sodium: an effective TxA2/PGH2 receptor antagonist". Cardiovascular Drug Reviews.
  2. (December 2020). "Repurposing of a Thromboxane Receptor Inhibitor Based on a Novel Role in Metastasis Identified by Phenome-Wide Association Study". Molecular Cancer Therapeutics.
  3. (June 2016). "Antagonism of the thromboxane-prostanoid receptor is cardioprotective against right ventricular pressure overload". Pulmonary Circulation.
  4. (August 2000). "Disposition of radiolabeled ifetroban in rats, dogs, monkeys, and humans". Drug Metabolism and Disposition.
  5. (November 2019). "Antagonism of the Thromboxane-Prostanoid Receptor as a Potential Therapy for Cardiomyopathy of Muscular Dystrophy". Journal of the American Heart Association.
  6. {{ClinicalTrialsGov. NCT03694249. A Pilot Trial of Ifetroban, A Thromboxane A2 Receptor Antagonist, in Patients With Malignant Solid Tumors at High Risk of Metastatic Recurrence
  7. {{ClinicalTrialsGov. NCT03962855. The Thromboxane Receptor Antagonist to Blunt the Effects of Non-Platelet Thromboxane Generation and Improve Endothelial Cell Function (TRAP) Trial
  8. {{ClinicalTrialsGov. NCT02216357. A Multicenter, Double-Blind, Randomized, Placebo-Controlled Trial to Determine the Safety of Oral Ifetroban in Patients With a History of Aspirin Exacerbated Respiratory Disease
  9. {{ClinicalTrialsGov. NCT03326063. Therapeutic Control of Aspirin-Exacerbated Respiratory Disease
  10. {{ClinicalTrialsGov. NCT03028350. A Phase 2 Multicenter, Double-blind, Randomized, Placebo-Controlled Trial to Evaluate Oral Ifetroban in Subjects With Symptomatic Aspirin Exacerbated Respiratory Disease (AERD)
  11. {{ClinicalTrialsGov. NCT02682511. A Phase 2 Multicenter, Randomized, Double-blind, Placebo-controlled Study to Assess the Safety and Efficacy of Ifetroban in Patients With Diffuse Cutaneous Systemic Sclerosis (SSc) or SSc-associated Pulmonary Arterial Hypertension (SSc-PAH)
  12. {{ClinicalTrialsGov. NCT03340675. A Randomized, Double-Blind, Placebo-Controlled, Multiple Dose Study With an Open-Label Extension to Determine the Safety, Pharmacokinetics and Efficacy of Oral Ifetroban in Subjects With Duchenne Muscular Dystrophy
  13. Drugs Future (c.f. Lednicer book 6)

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oxazolespentyl-compoundsexperimental-drugs