| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Piretanide targets the Na-K-2Cl cotransporter (NKCC2) in the thick ascending limb of the loop of Henle in the kidney. It works by inhibiting the reabsorption of sodium and chloride ions in this segment, leading to increased excretion of water, sodium, chloride, and other electrolytes. This potent diuretic action makes it effective for treating edema and hypertension. Its mechanism is similar to other loop diuretics such as furosemide and bumetanide.
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| ln Vitro |
Piretanide's in vitro activity is characterized by its inhibition of the Na-K-2Cl cotransporter. In isolated kidney tubule preparations, it inhibits sodium and chloride reabsorption in the thick ascending limb. Its potency (IC50) for NKCC2 inhibition is comparable to other loop diuretics. The compound's effects on electrolyte transport and renal function are well-characterized. However, detailed quantitative in vitro data are limited in publicly available sources.
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| ln Vivo |
Piretanide demonstrates potent diuretic activity in vivo. In animal models and human studies, it increases urine output and promotes excretion of sodium, chloride, and water. It is effective in treating edema associated with congestive heart failure, liver cirrhosis, and renal disease. It also has antihypertensive effects. Its oral activity and relatively favorable safety profile support its clinical use. It has potassium-sparing properties that offer potential advantages over other loop diuretics.
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| Enzyme Assay |
As a loop diuretic, Piretanide does not have established receptor binding assay protocols. Its activity is assessed by measuring electrolyte transport in kidney tubule preparations or by evaluating diuretic efficacy in vivo. Physical properties: melting point 225-227°C; solubility: very slightly soluble in water. Storage: 2-8°C. No specific enzyme or receptor binding assays are applicable for this compound.
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| Cell Assay |
Cellular studies with Piretanide are conducted in kidney cell lines (e.g., MDCK cells) or primary cultures of renal tubular cells. Cells are cultured in appropriate media and treated with Piretanide at various concentrations. Ion transport is measured using electrophysiological techniques (Ussing chamber, patch clamp) or by measuring ion flux with radioactive tracers (22Na, 36Cl). Cell viability is assessed using MTT or LDH assays. Each experiment includes other loop diuretics (furosemide, bumetanide) as positive controls and vehicle controls.
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| Animal Protocol |
In vivo studies of Piretanide are conducted in animal models (rats, dogs) and in humans. Diuretic efficacy is assessed by measuring urine volume, electrolyte excretion (sodium, potassium, chloride), and body weight changes. The compound is administered orally or intravenously at various doses. For hypertension studies, blood pressure is measured by telemetry or tail-cuff methods. Edema models (e.g., congestive heart failure, nephrotic syndrome) are used to evaluate therapeutic efficacy. Sample sizes typically range from 6-10 animals per group.
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| ADME/Pharmacokinetics |
Piretanide has a molecular weight of 362.40 g/mol and a molecular formula of C17H18N2O5S. Melting point: 225-227°C. Solubility: very slightly soluble in water. Storage: 2-8°C. It is orally active. Pharmacokinetic parameters: it is absorbed from the gastrointestinal tract, metabolized in the liver, and excreted renally. Half-life is approximately 1-2 hours. Bioavailability is around 60-80%.
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| Toxicity/Toxicokinetics |
Piretanide is generally well-tolerated at therapeutic doses. Common adverse effects may include electrolyte imbalances (hypokalemia, hyponatremia), dehydration, and hypotension. It may cause ototoxicity at high doses, similar to other loop diuretics. It is contraindicated in patients with anuria, severe electrolyte depletion, and hypersensitivity to sulfonamides. Standard toxicology studies have demonstrated an acceptable safety profile. It has been clinically evaluated for congestive heart failure and hypertension.
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| References |
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| Additional Infomation |
Piretanide is an aromatic ether. Piretanide (international nonproprietary name: pirantanib, trade names: Arelix, Eurelix, Tauliz) was synthesized in 1973 by Hoechst AG in Germany and is a loop diuretic. Its synthesis employed a then-novel method, namely, introducing cyclic amine residues into the aromatic nucleus in the presence of other aromatic functional groups. Piretanide is a sulfonylbenzoic acid drug, belonging to the loop diuretic class. The structure of pirantanib is related to that of furosemide and bumetanib.
Piretanide is also known as 4-Phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid. It is a high-ceiling loop diuretic structurally related to furosemide and bumetanide. It is used to treat edema associated with congestive heart failure, liver cirrhosis, and renal disease, as well as hypertension. It has potassium-sparing properties. Clinical trials and regulatory approvals have been reported for these indications. |
| Molecular Formula |
C17H18N2O5S
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|---|---|
| Molecular Weight |
362.4
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| Exact Mass |
362.094
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| CAS # |
55837-27-9
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| PubChem CID |
4849
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| Appearance |
White to light yellow solid powder
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| Density |
1.415 g/cm3
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| Boiling Point |
597.7ºC at 760 mmHg
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| Melting Point |
225-227°C (lit.)
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| Flash Point |
315.3ºC
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| Index of Refraction |
1.64
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| LogP |
4.27
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
25
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| Complexity |
564
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(O)C1=CC(S(=O)(N)=O)=C(OC2=CC=CC=C2)C(N3CCCC3)=C1
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| InChi Key |
UJEWTUDSLQGTOA-UHFFFAOYSA-N
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| 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)
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| Chemical Name |
4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid
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| Synonyms |
Arelix Tauliz Piretanide
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~689.85 mM)
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| 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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