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Rupatadine Fumarate (UR-12592; UR12592; Pafinur; Rupax; Rupafin; Alergoliber; Rinialer; Ralif), the fumarate salt of Rupatadine, is a potent inhibitor of PAFR and antagonist of histamine (H1) receptor used to treat allergies. Its Kis values for the PAFR and histamine (H1) receptors are 550 nM and 102 nM, respectively.
Physicochemical Properties
| Molecular Formula | C30H30CLN3O4 | |
| Molecular Weight | 532.03 | |
| Exact Mass | 531.192 | |
| Elemental Analysis | C, 67.73; H, 5.68; Cl, 6.66; N, 7.90; O, 12.03 | |
| CAS # | 182349-12-8 | |
| Related CAS # | Rupatadine; 158876-82-5; Rupatadine-d4 fumarate; 1795153-63-7 | |
| PubChem CID | 6449107 | |
| Appearance | White to off-white solid powder | |
| Boiling Point | 586.4ºC at 760 mmHg | |
| Melting Point | 58-61ºC | |
| Flash Point | 308.4ºC | |
| LogP | 5.284 | |
| Hydrogen Bond Donor Count | 2 | |
| Hydrogen Bond Acceptor Count | 7 | |
| Rotatable Bond Count | 4 | |
| Heavy Atom Count | 38 | |
| Complexity | 728 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | ClC1C([H])=C([H])C2=C(C=1[H])C([H])([H])C([H])([H])C1C([H])=C([H])C([H])=NC=1/C/2=C1/C([H])([H])C([H])([H])N(C([H])([H])C2=C([H])N=C([H])C(C([H])([H])[H])=C2[H])C([H])([H])C/1([H])[H].O([H])C(/C(/[H])=C(\[H])/C(=O)O[H])=O |
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| InChi Key | JYBLCDXVHQWMSU-WLHGVMLRSA-N | |
| InChi Code | InChI=1S/C26H26ClN3.C4H4O4/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25;5-3(6)1-2-4(7)8/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+ | |
| Chemical Name | (E)-but-2-enedioic acid;13-chloro-2-[1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene]-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene | |
| Synonyms |
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| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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| 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
| Targets | H1 Receptor ( Ki = 0.1 μM ); PAF ( Ki = 0.55 μM ) | ||
| ln Vitro |
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| ln Vivo |
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| Enzyme Assay | For 30 minutes at 25 °C, antagonists are incubated with guinea pig cerebellum membranes (0.6 mg/ml) and [3H]-pyrilamine (1.2 nM) in 0.5 ml of 50 mM PBS. The membranes are collected on Whatman GF/B filters and 5 ml of ice-cold PBS containing 2 μM pyrilamine is added to end the incubation. After that, the filters are placed in counting vials after being cleaned with 3 x 5 ml of ice-cold PBS plus 2 μM pyrilamine. Liquid scintillation counting in 3 ml of HiSafe 3 is used to determine the amount of radioactivity retained by each filter. The difference between the [3H]-pyrilamine bound in the absence and in the presence of a large molar excess (10 μM) of unlabeled promethazine allows for the determination of specific binding. | ||
| Cell Assay | C18-PAF is used to induce platelet aggregation, which is then measured with a dual-channel aggregometer Chrono-log 560. Platelet aggregation is measured both with and without the test compounds (5-min incubation). The inhibitors' activity is represented by their IC50 values. Rupatadine is tested in WRP against other aggregating agents, such as arachidonic acid (1 mM) and ADP (5 μM), in order to determine its selectivity. Rupatadine is present at different concentrations (3 × 10-7–3 × 10-5 M) and in the absence to obtain dose-response curves for PAF-induced aggregation in WRP. | ||
| Animal Protocol |
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| References |
[1]. J Pharmacol Exp Ther . 1997 Jan;280(1):114-21. [2]. Inflamm Res . 2000 Jul;49(7):355-60. [3]. Neuropsychobiology . 2004;50(4):311-21. [4]. Indian J Otolaryngol Head Neck Surg . 2009 Dec;61(4):320-32. |
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| Additional Infomation |
Drug Indication Treatment of allergic rhinitis, Treatment of chronic idiopathic urticaria |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.91 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 20.8 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: ≥ 2.08 mg/mL (3.91 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 20.8 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: ≥ 2.08 mg/mL (3.91 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 30% Propylene glycol , 5% Tween 80 , 65% D5W: 30 mg/mL (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8796 mL | 9.3980 mL | 18.7959 mL | |
| 5 mM | 0.3759 mL | 1.8796 mL | 3.7592 mL | |
| 10 mM | 0.1880 mL | 0.9398 mL | 1.8796 mL |