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Umifenovir (trade name Arbidol) HCl, the hydrochloride salt of umifenovir, is a broad-spectrum antiviral drug that blocks viral fusion, and was approved for use in Russia and China for the treatment of influenza and other respiratory viral infections. Arbidol inhibits the cell entry of HCV pseudoparticles of genotypes 1a, 1b, and 2a in a dose-dependent fashion. Arbidol also displays a dose-dependent inhibition of HCV membrane fusion, as assayed by using HCV pseudoparticles (HCVpp) and fluorescent liposomes. Arbidol is found to present potent inhibitory activity against enveloped and non-enveloped RNA viruses, including FLU-A, RSV, HRV 14 and CVB3 when added before, during, or after viral infection, with IC50 ranging from 2.7 to 13.8 mg/mL.
Physicochemical Properties
| Molecular Formula | C22H25BRN2O3S.HCL |
| Molecular Weight | 513.88 |
| Exact Mass | 512.053 |
| Elemental Analysis | C, 51.42; H, 5.10; Br, 15.55; Cl, 6.90; N, 5.45; O, 9.34; S, 6.24 |
| CAS # | 131707-23-8 |
| Related CAS # | Umifenovir;131707-25-0;Umifenovir-d6 hydrochloride |
| PubChem CID | 9958103 |
| Appearance | White to off-white crystalline powder. |
| Boiling Point | 591.8ºC at 760 mmHg |
| Melting Point | 133-137ºC |
| Flash Point | 311.7℃ |
| Vapour Pressure | 1.34E-14mmHg at 25°C |
| LogP | 5.979 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 30 |
| Complexity | 546 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | BrC1=C(C(C([H])([H])N(C([H])([H])[H])C([H])([H])[H])=C2C(C(=O)OC([H])([H])C([H])([H])[H])=C(C([H])([H])SC3C([H])=C([H])C([H])=C([H])C=3[H])N(C([H])([H])[H])C2=C1[H])O[H].Cl[H] |
| InChi Key | OMZHXQXQJGCSKN-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C22H25BrN2O3S.ClH/c1-5-28-22(27)20-18(13-29-14-9-7-6-8-10-14)25(4)17-11-16(23)21(26)15(19(17)20)12-24(2)3;/h6-11,26H,5,12-13H2,1-4H3;1H |
| Chemical Name | ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-1H-indole-3-carboxylate hydrochloride |
| Synonyms | Umifenovir; Umifenovir HCl; Umifenovir hydrochloride; arbidol. |
| 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. |
| 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 |
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| ln Vivo |
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| Animal Protocol |
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| References | Biochemistry.2007 May 22;46(20):6050-9;Arch Virol.2007;152(8):1447-55;J Med Virol.2012 Jan;84(1):170-81. |
Solubility Data
| Solubility (In Vitro) |
DMSO :25 ~ 100 mg/mL ( 48.65 ~194.59 mM ) H2O : < 0.1 mg/mL Ethanol : ~50 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.86 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 25.0 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: ≥ 2.5 mg/mL (4.86 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 25.0 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: ≥ 2.5 mg/mL (4.86 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (4.86 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9460 mL | 9.7299 mL | 19.4598 mL | |
| 5 mM | 0.3892 mL | 1.9460 mL | 3.8920 mL | |
| 10 mM | 0.1946 mL | 0.9730 mL | 1.9460 mL |