Physicochemical Properties
| Molecular Formula | C20H21N3O4 |
| Molecular Weight | 367.39800 |
| Exact Mass | 367.153 |
| CAS # | 148396-36-5 |
| Related CAS # | Fradafiban hydrochloride |
| PubChem CID | 66000 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.38g/cm3 |
| Index of Refraction | 1.659 |
| LogP | 3.124 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 27 |
| Complexity | 551 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | O=C(O)C[C@H]1C(N[C@H](COC2=CC=C(C3=CC=C(C(N)=N)C=C3)C=C2)C1)=O |
| InChi Key | IKZACQMAVUIGPY-HOTGVXAUSA-N |
| InChi Code | InChI=1S/C20H21N3O4/c21-19(22)14-3-1-12(2-4-14)13-5-7-17(8-6-13)27-11-16-9-15(10-18(24)25)20(26)23-16/h1-8,15-16H,9-11H2,(H3,21,22)(H,23,26)(H,24,25)/t15-,16-/m0/s1 |
| Chemical Name | 2-[(3S,5S)-5-[[4-(4-carbamimidoylphenyl)phenoxy]methyl]-2-oxopyrrolidin-3-yl]acetic acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Fradafiban is a non-peptide mimic of the arginine-glycine-aspartate recognition sequence. Fradafiban binds to the human platelet GP IIb/IIIa complex with great affinity and selectivity and efficiently suppresses human platelet aggregation in vitro. Fradafiban reversibly binds to the human platelet GP IIb/IIIa complex with a Kd value of 148 nM [1]. |
| ln Vivo | Fradafiban exhibits relatively little oral action, which may be related to its greater polarity and thus low absorption when taken orally [1]. |
| References |
[1]. Profound and sustained inhibition of platelet aggregation by Fradafiban, a nonpeptide platelet glycoprotein IIb/IIIa antagonist, and its orally active prodrug, Lefradafiban, in men. Circulation. 1997 Aug 19;96(4):1130-8. |
| Additional Infomation |
Fradafiban is a pyrrolidinone that is pyrrolidin-2-one which is substituted at positions 3 and 5 by carboxymethyl and hydroxymethyl groups, respectively, and in which the hydrogen of the resulting alcoholic hydroxy group is replaced by a 4'-carbamimidoylbiphenyl-4-yl group (the S,S-diastereoisomer). A figrinogen receptor antagonist. It has a role as a platelet glycoprotein-IIb/IIIa receptor antagonist. It is a monocarboxylic acid, a carboxamidine and a member of pyrrolidin-2-ones. Drug Indication Investigated for use/treatment in angina. Mechanism of Action Fradafiban is a glycoprotein IIb/IIIa receptor antagonist. Activation of the platelet glycoprotein (GP IIb/IIIa) receptor on the platelet surface is the final pathway of platelet aggregation that may lead to embolism, which is one on the cause of angina. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~180 mg/mL (~489.93 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.25 mg/mL (6.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 22.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.25 mg/mL (6.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 22.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.25 mg/mL (6.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 22.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7218 mL | 13.6091 mL | 27.2183 mL | |
| 5 mM | 0.5444 mL | 2.7218 mL | 5.4437 mL | |
| 10 mM | 0.2722 mL | 1.3609 mL | 2.7218 mL |