Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H25N3O6 |
Molecular Weight | 439.4611 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C[C@@H]1C[C@@H](COC2=CC=C(C=C2)C3=CC=C(C=C3)C(=N)NC(=O)OC)NC1=O
InChI
InChIKey=PGCFXITVMNNKON-ROUUACIJSA-N
InChI=1S/C23H25N3O6/c1-30-20(27)12-17-11-18(25-22(17)28)13-32-19-9-7-15(8-10-19)14-3-5-16(6-4-14)21(24)26-23(29)31-2/h3-10,17-18H,11-13H2,1-2H3,(H,25,28)(H2,24,26,29)/t17-,18-/m0/s1
DescriptionSources: https://adisinsight.springer.com/drugs/800005284 | https://www.ncbi.nlm.nih.gov/pubmed/11250974https://www.ncbi.nlm.nih.gov/pubmed/9825033Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04863 | https://clinicaltrials.gov/ct2/show/NCT02264119 | https://www.ncbi.nlm.nih.gov/pubmed/11154975 | https://www.ncbi.nlm.nih.gov/pubmed/11250974
Sources: https://adisinsight.springer.com/drugs/800005284 | https://www.ncbi.nlm.nih.gov/pubmed/11250974https://www.ncbi.nlm.nih.gov/pubmed/9825033
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04863 | https://clinicaltrials.gov/ct2/show/NCT02264119 | https://www.ncbi.nlm.nih.gov/pubmed/11154975 | https://www.ncbi.nlm.nih.gov/pubmed/11250974
Lefradafiban, an orally active prodrug of fradafiban, is a novel glycoprotein (IIb/IIIa) inhibitor for the treatment of unstable angina. The pharmacokinetic and pharmacodynamic properties of lefradafiban were assessed in 130 healthy male volunteers who received a single dose of 10, 50, 75, 100, or 150 mg or multiple doses of 25, 50, 60, 75, 90, or 100 mg three times daily for one week. After both single and multiple doses, receptor occupancy and plasma lefradafiban levels correlated with platelet aggregation. Lefradafiban had been in phase II clinical trials by Boehringer Ingelheim for the treatment of thrombosis. However, it has been terminated.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10544919 |
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Target ID: CHEMBL2093869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9286940 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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158 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11250974 |
30 mg 3 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
FRADAFIBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
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314 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11250974 |
45 mg 3 times / day steady-state, oral dose: 45 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
FRADAFIBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
394 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11250974 |
60 mg 3 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
FRADAFIBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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Profound and sustained inhibition of platelet aggregation by Fradafiban, a nonpeptide platelet glycoprotein IIb/IIIa antagonist, and its orally active prodrug, Lefradafiban, in men. | 1997 Aug 19 |
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Fradafiban. BIBU 52, BIBU 52 ZW. | 1999 May |
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Pharmacodynamics and safety of lefradafiban, an oral platelet glycoprotein IIb/IIIa receptor antagonist, in patients with stable coronary artery disease undergoing elective angioplasty. | 2001 Apr |
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Clinical trials with glycoprotein IIb/IIIa antagonists - No benefit without bleeding? | 2001 Aug |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11102255
20, 30 and 45 mg t.i.d. of lefradafiban were used in phase II dose-escalation trial
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://circ.ahajournals.org/content/96/4/1130.short
One to 15 mg Fradafiban continuously infused over 30 minutes reversibly inhibited platelet aggregation in platelet-rich plasma ex vivo in response to 20 μmol/L ADP (5 mg, 100% inhibition at 27 minutes after administration) and to both 1.0 (5 mg, 100%) and 10 μg/mL (15 mg, 97±3%) collagen.
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NCI_THESAURUS |
C1327
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0R4888YXR5
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CHEMBL2105032
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C107918
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132881
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7277
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DB04863
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100000082566
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149503-79-7
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DTXSID80164331
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60634
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C81565
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SUB08425MIG
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ACTIVE MOIETY
SUBSTANCE RECORD