Piretanide (Eurelix; Tauliz; Arelix) is a novel and potent loop diuretic acting as a time- and voltage-dependent blocker of CFTR Cl(-) currents. It has potential to be used for hypertension and CHF/congestive heart failure with a potential advantage of having potassium-sparing properties.
Physicochemical Properties
| Molecular Formula | C17H18N2O5S |
| Molecular Weight | 362.4 |
| Exact Mass | 362.094 |
| CAS # | 55837-27-9 |
| PubChem CID | 4849 |
| Appearance | White to light yellow solid powder |
| Density | 1.415 g/cm3 |
| Boiling Point | 597.7ºC at 760 mmHg |
| Melting Point | 225-227°C (lit.) |
| Flash Point | 315.3ºC |
| Index of Refraction | 1.64 |
| LogP | 4.27 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 25 |
| Complexity | 564 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(O)C1=CC(S(=O)(N)=O)=C(OC2=CC=CC=C2)C(N3CCCC3)=C1 |
| InChi Key | UJEWTUDSLQGTOA-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C17H18N2O5S/c18-25(22,23)15-11-12(17(20)21)10-14(19-8-4-5-9-19)16(15)24-13-6-2-1-3-7-13/h1-3,6-7,10-11H,4-5,8-9H2,(H,20,21)(H2,18,22,23) |
| Chemical Name | 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid |
| Synonyms | Arelix Tauliz Piretanide |
| 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
| References |
[1].Carda-Broch S, et al. Analysis of urine samples containing cardiovascular drugs by micellar liquid chromatography with fluorimetric detection. J Chromatogr Sci. 1999;37(4):93-102. [2].Sherman LG, et al. Piretanide, a potent diuretic with potassium-sparing properties, for the treatment of congestive heart failure. Clin Pharmacol Ther. 1986;40(5):587-594. |
| Additional Infomation |
Piretanide is an aromatic ether. Piretanide (INN, trade names Arelix, Eurelix, Tauliz) has been synthesized in 1973 at Hoechst AG (Germany) as a loop diuretic compound by using a then-new method for introducing cyclic amine residues in an aromatic nucleus in the presence of other aromatically bonded functional groups. Piretanide is a sulfamoylbenzoic acid belonging to the class of loop diuretics. Piretanide is structurally related to furosemide and bumetanide. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~689.85 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.74 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 (5.74 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7594 mL | 13.7969 mL | 27.5938 mL | |
| 5 mM | 0.5519 mL | 2.7594 mL | 5.5188 mL | |
| 10 mM | 0.2759 mL | 1.3797 mL | 2.7594 mL |