Pipemidic acid trihydrate is an analogue of Piromidic acid and is an antibacterial agent. Pipemidic acid trihydrate inhibits DNA gyrase. Pipemidic acid trihydrate has activity against Gram-negative (Gram+) bacteria such as Pseudomonas aeruginosa, and certain Gram-positive (Gram+) bacteria. Pipemidic acid trihydrate may be utilized to study intestinal, urinary and biliary tract infections.

Physicochemical Properties

Molecular Formula	C14H23N5O6
Molecular Weight	357.36
Exact Mass	303.133
CAS #	72571-82-5
Related CAS #	Pipemidic acid;51940-44-4
PubChem CID	153398
Appearance	Typically exists as solid at room temperature
Density	1.41g/mLat 25°C (lit.)
Boiling Point	534.9ºC at 760 mmHg
Melting Point	253-255°
Flash Point	277.3ºC
LogP	0.313
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	3
Heavy Atom Count	25
Complexity	489
Defined Atom Stereocenter Count	0
SMILES	CCN1C=C(C(=O)C2=CN=C(N=C21)N3CCNCC3)C(=O)O.O.O.O
InChi Key	URMXYPLWYMOYPG-UHFFFAOYSA-N
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
Chemical Name	8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid;trihydrate
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

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].
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].
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	Pipemidic acid trihydrate is a N-arylpiperazine.

Solubility Data

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

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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (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.