![Pipemidic acid trihydrate (8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyridine[2,3-D]pyrimidine-6-carboxylic acid)](/upload/1124/hy-w013766.png)
| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Pipemidic acid targets bacterial DNA gyrase (topoisomerase II) and topoisomerase IV. It binds the enzyme-DNA complex and inhibits DNA supercoiling and replication, leading to bacterial cell death. It is bactericidal against susceptible organisms. It has limited activity against Gram-positive bacteria.
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| ln Vitro |
Pipemidic acid trihydrate is a bacterial enzyme that inhibits DNA gyrase, which is responsible for the ATP-dependent negative supercoiling of DNA[2].
In vitro, pipemidic acid is active against Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, and Pseudomonas aeruginosa. MIC values typically range from 0.5 to 8 µg/mL. It is less active than fluoroquinolones such as ciprofloxacin. It has some activity against Staphylococcus aureus at higher concentrations. |
| ln Vivo |
Pipemidic acid (50 mg/kg) trihydrate is effectively absorbed orally, and in mice, rats, dogs, and primates, the peak plasma levels varied from 4 to 12 μg/mL[3]. In mice, the average fatal dose of pipemidic acid trihydrate following a single oral dosage was greater than 16000 mg/kg[3].
In vivo, pipemidic acid is effective in urinary tract infections in humans. It is administered orally and achieves high urinary concentrations. It is less effective than fluoroquinolones for systemic infections. It is not widely used clinically due to the availability of more potent fluoroquinolones. |
| Enzyme Assay |
For non-cell enzyme assays, purified DNA gyrase or topoisomerase IV is incubated with pipemidic acid and supercoiled DNA. DNA supercoiling or relaxation is measured by agarose gel electrophoresis. IC50 values are calculated from dose-response curves. DNA cleavage assays measure enzyme-mediated DNA breakage.
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| Cell Assay |
In cell assays, bacterial strains are grown in Mueller-Hinton broth. Pipemidic acid is serially diluted in 96-well plates and inoculated. After incubation at 35-37°C for 16-20 hours, MIC is determined by visual or spectrophotometric growth inhibition. Time-kill assays measure viable colony counts.
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| Animal Protocol |
In vivo animal protocols use mice with systemic or urinary tract infection. Pipemidic acid is administered orally at doses of 10-100 mg/kg. Survival, bacterial load in urine and tissues, and histopathology are assessed. Pharmacokinetics are measured by HPLC or LC-MS.
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| References |
[1]. Iacovino R, et al. β-Cyclodextrin inclusion complex to improve physicochemical properties of pipemidic acid: characterization and bioactivity evaluation. Int J Mol Sci. 2013 Jun 25;14(7):13022-41.
[2]. Aoyama H, et, al. Purification of Citrobacter freundii DNA gyrase and inhibition by quinolones. Antimicrob Agents Chemother. 1988 Jan;32(1):104-9. [3]. Shimizu M, et, al. Pipemidic acid: absorption, distribution, and excretion. Antimicrob Agents Chemother. 1975 Apr;7(4):441-6. |
| Additional Infomation |
Piperamide trihydrate is an N-arylpiperazine.
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| Molecular Formula |
C14H23N5O6
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| Molecular Weight |
357.36
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| Exact Mass |
303.133
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| CAS # |
72571-82-5
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| Related CAS # |
Pipemidic acid;51940-44-4
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| PubChem CID |
153398
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| Appearance |
White to off-white solid
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| Density |
1.41g/mLat 25°C (lit.)
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| Boiling Point |
534.9ºC at 760 mmHg
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| Melting Point |
253-255°
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| Flash Point |
277.3ºC
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| LogP |
0.313
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
25
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| Complexity |
489
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCN1C=C(C(=O)C2=CN=C(N=C21)N3CCNCC3)C(=O)O.O.O.O
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| InChi Key |
URMXYPLWYMOYPG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H17N5O3.3H2O/c1-2-18-8-10(13(21)22)11(20)9-7-16-14(17-12(9)18)19-5-3-15-4-6-19;;;/h7-8,15H,2-6H2,1H3,(H,21,22);3*1H2
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| Chemical Name |
8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid;trihydrate
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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 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7983 mL | 13.9915 mL | 27.9830 mL | |
| 5 mM | 0.5597 mL | 2.7983 mL | 5.5966 mL | |
| 10 mM | 0.2798 mL | 1.3991 mL | 2.7983 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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