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Structure via PubChem · Public domain (PubChem)
Ifetroban
Sign in to saveIfetroban 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.
Chemical data
- Formula
- C25H32N2O5
- Molecular weight
- 440.5 g/mol
- IUPAC name
- 3-[2-[[(1S,2R,3S,4R)-3-[4-(pentylcarbamoyl)-1,3-oxazol-2-yl]-7-oxabicyclo[2.2.1]heptan-2-yl]methyl]phenyl]propanoic acid
- SMILES
- CCCCCNC(=O)C1=COC(=N1)[C@@H]2[C@H]3CC[C@@H]([C@@H]2CC4=CC=CC=C4CCC(=O)O)O3
- InChIKey
- BBPRUNPUJIUXSE-DXKRWKNPSA-N
- XLogP
- 4
- Polar surface area
- 102 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- respiratory system disease, asthma, hepatorenal syndrome
via ChEMBL · EBI
Research
65 papers- Ifetroban sodium: an effective TxA2/PGH2 receptor antagonist.Cardiovascular drug reviews · 2001
- Ifetroban reduces coronary artery dysfunction in a mouse model of Duchenne muscular dystrophy.American journal of physiology. Heart and circulatory physiology · 2021
- Trial of thromboxane receptor inhibition with ifetroban: TP receptors regulate eicosanoid homeostasis in aspirin-exacerbated respiratory disease.The Journal of allergy and clinical immunology · 2023
- Targeting platelet-tumor cell interactions via thromboxane A(2)-prostanoid receptor blockade to reduce metastasis in triple negative breast cancer.Experimental hematology & oncology · 2025
- Effect of ifetroban, a thromboxane A2 receptor antagonist, in stroke-prone spontaneously hypertensive rats.Clinical and experimental hypertension (New York, N.Y. : 1993) · 1996
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 440.2311221239999
Show 5 more facts
- chemical formula
- C₂₅H₃₂N₂O₅
- canonical SMILES
- CCCCCNC(=O)C1=COC(=N1)C2C3CCC(C2CC4=CC=CC=C4CCC(=O)O)O3
- subject has role
- platelet aggregation inhibitors
- isomeric SMILES
- CCCCCNC(=O)C1=COC(=N1)[C@@H]2[C@H]3CC[C@@H]([C@@H]2CC4=CC=CC=C4CCC(=O)O)O3
- Commons category
- Ifetroban
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
{{Drugbox | 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 =
Excerpted from Wikipedia’s “Ifetroban” article, available under the CC BY-SA 4.0 licence.