Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H32N2O5 |
Molecular Weight | 440.532 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCNC(=O)C1=COC(=N1)[C@@H]2[C@H]3CC[C@H](O3)[C@@H]2CC4=C(CCC(O)=O)C=CC=C4
InChI
InChIKey=BBPRUNPUJIUXSE-DXKRWKNPSA-N
InChI=1S/C25H32N2O5/c1-2-3-6-13-26-24(30)19-15-31-25(27-19)23-18(20-10-11-21(23)32-20)14-17-8-5-4-7-16(17)9-12-22(28)29/h4-5,7-8,15,18,20-21,23H,2-3,6,9-14H2,1H3,(H,26,30)(H,28,29)/t18-,20-,21+,23-/m0/s1
Ifetroban was developed as a thromboxane A2/prostaglandin H2 receptor antagonist by Bristol-Myers Squibb for cardiovascular indications. In spite of the positive preclinical results where the drug has shown the cardioprotective and antithrombotic activities and was effective. The development of this drug for coronary thrombosis, peripheral vascular disorders, and thrombosis was discontinued. Bristol-Myers Squibb donated the entire program to Vanderbilt University, which further identified ifetroban’s potential in treating patients for several niche indications. Cumberland acquired the ifetroban program from Vanderbilt through its majority-owned subsidiary, Cumberland Emerging Technologies taking responsibility for development and commercialization of the product. Ifetroban oral capsule is being developed by Cumberland for the treatment of systemic sclerosis (SSc) also called scleroderma. With pulmonary disease emerging as the major cause of death in SSc patients, preclinical work indicates that ifetroban is capable of preventing cardiac fibrosis in a model of pulmonary arterial hypertension. In addition, this drug successfully completed phase II clinical trials for the treatment of hepatorenal syndrome (HRS) in hospitalized adult patients, where were determined the safety and pharmacokinetics of 3 days of intravenous ifetroban. In addition, the recruitment is anticipated for Phase 2 study of daily, oral anti-fibrotic therapy to prevent heart muscle disease and improve heart muscle function in ambulatory and non-ambulatory Duchenne patients. In December 2018, Vanderbilt-Ingram Cancer Center and Cumberland Pharmaceuticals initiated a phase II trial to assess the safety and feasibility of ifetroban in treating patients with malignant solid tumors that are at high risk of coming back after treatment and spreading throughout the body.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P21731 Gene ID: 6915.0 Gene Symbol: TBXA2R Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11484065 |
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Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11484065 |
PubMed
Title | Date | PubMed |
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Pharmacological profile of BMS 180,291: a potent, long-acting, orally active thromboxane A2/prostaglandin endoperoxide receptor antagonist. | 1993 Feb |
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Dose-related cardioprotection by ifetroban in relation to inhibition of thrombosis and ex vivo platelet function. | 1995 Feb |
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Ifetroban sodium: an effective TxA2/PGH2 receptor antagonist. | 2001 Summer |
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C1327
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)