U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of IFETROBAN

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

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P21731
Gene ID: 6915.0
Gene Symbol: TBXA2R
Target Organism: Homo sapiens (Human)
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Pharmacological profile of BMS 180,291: a potent, long-acting, orally active thromboxane A2/prostaglandin endoperoxide receptor antagonist.
1993 Feb
Dose-related cardioprotection by ifetroban in relation to inhibition of thrombosis and ex vivo platelet function.
1995 Feb
Ifetroban sodium: an effective TxA2/PGH2 receptor antagonist.
2001 Summer

Sample Use Guides

hepatorenal syndrome (HRS): 60-minute intravenous infusion of 5 mg ifetroban given once daily for 3 days to subjects with Type 1 HRS Oral Ifetroban in Subjects With Duchenne Muscular Dystrophy:
Route of Administration: Other
Name Type Language
IFETROBAN
INN   USAN  
INN   USAN  
Official Name English
IFETROBAN [USAN]
Common Name English
ifetroban [INN]
Common Name English
O-[[1S,2R,3S,4R)-3-[4-(Pentylcarbamoyl)-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]hydrocinnamic acid
Common Name English
BENZENEPROPANOIC ACID, 2-((3-(4-((PENTYLAMINO)CARBONYL)-2-OXAZOLYL)-7-OXABICYCLO(2.2.1)HEPT-2-YL)METHYL)-, (1S-(EXO,EXO))-
Common Name English
BMS-180291
Code English
Classification Tree Code System Code
NCI_THESAURUS C1327
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Code System Code Type Description
CAS
143443-90-7
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ChEMBL
CHEMBL3301673
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INN
7252
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WIKIPEDIA
IFETROBAN
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FDA UNII
E833KT807K
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EVMPD
SUB08124MIG
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EPA CompTox
DTXSID40869931
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USAN
EE-71
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SMS_ID
100000083700
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PUBCHEM
3037233
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NCI_THESAURUS
C81570
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DRUG BANK
DB12321
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