Pipemidic Acid hydrate
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MedKoo CAT#: 464557

CAS#: 72571-82-5 (hydrate)

Description: Pipemidic acid is an antibiotic and derivative of piromidic acid. It is active against clinical isolates of E. coli, P. mirabilis, P. inconstans, Shigella, Salmonella, Alcaligenes, and V. parahaemolyticus (MICs = 0.78-100 µg/ml), as well as drug-resistant clinical isolates of E. coli, P. mirabilis, Klebsiella, and Shigella (MICs = 1.56-6.25 µg/ml). Pipemidic acid is protective against systemic S. aureus, E. coli, K. pneumoniae, and P. aeruginosa infections in mice (ED50s = 237.5, 204.1, 28.6, and 99.5 mg/kg, respectively). It is also protective against P. aeruginosa-induced pulmonary and dermal infections (ED50s = 81.7 and 173.2 mg/kg, respectively), as well as E. coli, K. pneumoniae, and P. aeruginosa urinary bladder infections (ED50s = 4.8, 11.9, and 30.6 mg/kg, respectively), in mice.

Chemical Structure

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Pipemidic Acid hydrate
CAS# 72571-82-5 (hydrate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464557
Name: Pipemidic Acid hydrate
CAS#: 72571-82-5 (hydrate)
Chemical Formula: C14H23N5O6
Exact Mass: 357.16
Molecular Weight: 357.367
Elemental Analysis: C, 47.05; H, 6.49; N, 19.60; O, 26.86

Price and Availability

Size Price Availability Quantity
50mg USD -2 2 Weeks
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
2g USD -2 2 Weeks
1g USD 210 2 Weeks
5g USD 380 2 Weeks
10g USD 610 2 Weeks
25g USD 870 2 Weeks
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Related CAS #: 72571-82-5 (hydrate)   51940-44-4 (free)  

Synonym: Pipemidic Acid hydrate;

IUPAC/Chemical Name: 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid trihydrate

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

SMILES Code: O=C(O)C1=CN(C2=NC(N3CCNCC3)=NC=C2C1=O)CC.O.O.O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Pipemidic acid trihydrate inhibits DNA gyrase.
In vitro activity: The inclusion complex of HPPA with TRIMEB was prepared in solid state by the kneading method and confirmed by FT-IR and powered X-ray diffraction. The association in aqueous solutions of pipemidic acid with TRIMEB was investigated by UV-Vis spectroscopy. Job's plots have been drawn by UV-visible spectroscopy to confirm the 1:1 stoichiometry of the host⁻guest assembly. The antibacterial activity of HPPA, TRIMEB and of their complex was tested on Escherichia coli, Pseudomonas aeruginosa, and Staphilococcus aureus. The complex was able to increase 47.36% of the median antibacterial activity of the free HPPA against E. coli (IC50 = 249 µM vs. 473 µM). Furthermore, these samples were tested on HepG-2 and MCF-7. After 72 h, the median tumoral cytotoxicity exerted by the complex was increased by 78.08% and 94.27% for HepG-2 and MCF-7 respectively. Reference: Int J Mol Sci. 2019 Jan 18;20(2):416. https://pubmed.ncbi.nlm.nih.gov/30669399/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 0.5 1.40
DMSO 1.0 2.80
DMSO:PBS (pH 7.2) (1:4) 0.2 0.56

Preparing Stock Solutions

The following data is based on the product molecular weight 357.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Lavorgna M, Iacovino R, Russo C, Di Donato C, Piscitelli C, Isidori M. A New Approach for Improving the Antibacterial and Tumor Cytotoxic Activities of Pipemidic Acid by Including It in Trimethyl-β-cyclodextrin. Int J Mol Sci. 2019 Jan 18;20(2):416. doi: 10.3390/ijms20020416. PMID: 30669399; PMCID: PMC6359225. 2. Arriaga-Alba M, Barrón-Moreno F, Flores-Paz R, García-Jiménez E, Rivera-Sánchez R. Genotoxic evaluation of norfloxacin and pipemidic acid with the Escherichia coli Pol A-/Pol A+ and the ames test. Arch Med Res. 1998 Autumn;29(3):235-40. PMID: 9775457.
In vitro protocol: 1. Lavorgna M, Iacovino R, Russo C, Di Donato C, Piscitelli C, Isidori M. A New Approach for Improving the Antibacterial and Tumor Cytotoxic Activities of Pipemidic Acid by Including It in Trimethyl-β-cyclodextrin. Int J Mol Sci. 2019 Jan 18;20(2):416. doi: 10.3390/ijms20020416. PMID: 30669399; PMCID: PMC6359225. 2. Arriaga-Alba M, Barrón-Moreno F, Flores-Paz R, García-Jiménez E, Rivera-Sánchez R. Genotoxic evaluation of norfloxacin and pipemidic acid with the Escherichia coli Pol A-/Pol A+ and the ames test. Arch Med Res. 1998 Autumn;29(3):235-40. PMID: 9775457.
In vivo protocol: TBD

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2: Asmat U, Mumtaz MZ, Malik A. Rising prevalence of multidrug-resistant uropathogenic bacteria from urinary tract infections in pregnant women. J Taibah Univ Med Sci. 2020 Nov 11;16(1):102-111. doi: 10.1016/j.jtumed.2020.10.010. PMID: 33603638; PMCID: PMC7858016.

3: Ávila C, García-Galán MJ, Borrego CM, Rodríguez-Mozaz S, García J, Barceló D. New insights on the combined removal of antibiotics and ARGs in urban wastewater through the use of two configurations of vertical subsurface flow constructed wetlands. Sci Total Environ. 2021 Feb 10;755(Pt 2):142554. doi: 10.1016/j.scitotenv.2020.142554. Epub 2020 Sep 28. PMID: 33059136.

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5: Sun L, Zhu S, Zheng Z, Sun J, Zhao XE, Liu H. 9-Plex ultra high performance liquid chromatography tandem mass spectrometry determination of free hydroxyl polycyclic aromatic hydrocarbons in human plasma and urine. J Chromatogr A. 2020 Jul 19;1623:461182. doi: 10.1016/j.chroma.2020.461182. Epub 2020 May 6. PMID: 32505283.

6: Pokharel R, Li Q, Zhou L, Hanna K. Water Flow and Dissolved MnII Alter Transformation of Pipemidic Acid by Manganese Oxide. Environ Sci Technol. 2020 Jul 7;54(13):8051-8060. doi: 10.1021/acs.est.0c01474. Epub 2020 Jun 14. PMID: 32470299.

7: Alves PC, Rijo P, Bravo C, Antunes AMM, André V. Bioactivity of Isostructural Hydrogen Bonding Frameworks Built from Pipemidic Acid Metal Complexes. Molecules. 2020 May 20;25(10):2374. doi: 10.3390/molecules25102374. PMID: 32443884; PMCID: PMC7287797.

8: Rodriguez-Mozaz S, Vaz-Moreira I, Varela Della Giustina S, Llorca M, Barceló D, Schubert S, Berendonk TU, Michael-Kordatou I, Fatta-Kassinos D, Martinez JL, Elpers C, Henriques I, Jaeger T, Schwartz T, Paulshus E, O'Sullivan K, Pärnänen KMM, Virta M, Do TT, Walsh F, Manaia CM. Antibiotic residues in final effluents of European wastewater treatment plants and their impact on the aquatic environment. Environ Int. 2020 Jul;140:105733. doi: 10.1016/j.envint.2020.105733. Epub 2020 Apr 27. PMID: 32353669.

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10: Zhang L, Qin S, Shen L, Li S, Cui J, Liu Y. Bioaccumulation, trophic transfer, and human health risk of quinolones antibiotics in the benthic food web from a macrophyte-dominated shallow lake, North China. Sci Total Environ. 2020 Apr 10;712:136557. doi: 10.1016/j.scitotenv.2020.136557. Epub 2020 Jan 7. PMID: 31931207.

11: Craddock HA, Panthi S, Rjoub Y, Lipchin C, Sapkota A, Sapkota AR. Antibiotic and herbicide concentrations in household greywater reuse systems and pond water used for food crop irrigation: West Bank, Palestinian Territories. Sci Total Environ. 2020 Jan 10;699:134205. doi: 10.1016/j.scitotenv.2019.134205. Epub 2019 Aug 30. PMID: 33736191.

12: Soldevila S, Bosca F. Assessing physical properties of amphoteric fluoroquinolones using phosphorescence spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Feb 15;227:117569. doi: 10.1016/j.saa.2019.117569. Epub 2019 Oct 11. PMID: 31670049.

13: Tanaka E, Wajima T, Noguchi N. Earlier generation quinolones can be useful in identifying Haemophilus influenzae strains with low susceptibility to quinolone isolated from paediatric patients. J Med Microbiol. 2019 Aug;68(8):1227-1232. doi: 10.1099/jmm.0.001027. Epub 2019 Jun 19. PMID: 31215858.

14: Kulkarni P, Raspanti GA, Bui AQ, Bradshaw RN, Kniel KE, Chiu PC, Sharma M, Sapkota A, Sapkota AR. Zerovalent iron-sand filtration can reduce the concentration of multiple antimicrobials in conventionally treated reclaimed water. Environ Res. 2019 May;172:301-309. doi: 10.1016/j.envres.2019.02.012. Epub 2019 Feb 10. PMID: 30822564.

15: Zhang B, Wu Q, Wang Z, Xu R, Hu X, Sun Y, Wang Q, Ju F, Ren S, Zhang C, Qin L, Ma Q, Zhou YL. The promising novel biomarkers and candidate small molecule drugs in kidney renal clear cell carcinoma: Evidence from bioinformatics analysis of high-throughput data. Mol Genet Genomic Med. 2019 May;7(5):e607. doi: 10.1002/mgg3.607. Epub 2019 Feb 21. PMID: 30793530; PMCID: PMC6503072.

16: Lavorgna M, Iacovino R, Russo C, Di Donato C, Piscitelli C, Isidori M. A New Approach for Improving the Antibacterial and Tumor Cytotoxic Activities of Pipemidic Acid by Including It in Trimethyl-β-cyclodextrin. Int J Mol Sci. 2019 Jan 18;20(2):416. doi: 10.3390/ijms20020416. PMID: 30669399; PMCID: PMC6359225.

17: Pagani AP, Ibañez GA. Analytical approach for the simultaneous determination of quinolones in edible animal products. Modeling pH-modulated fluorescence excitation-emission matrices four-way arrays. Talanta. 2019 Jan 15;192:52-60. doi: 10.1016/j.talanta.2018.09.015. Epub 2018 Sep 6. PMID: 30348426.

18: Mathurin J , Pancani E , Deniset-Besseau A , Kjoller K , Prater CB , Gref R , Dazzi A . How to unravel the chemical structure and component localization of individual drug-loaded polymeric nanoparticles by using tapping AFM-IR. Analyst. 2018 Dec 3;143(24):5940-5949. doi: 10.1039/c8an01239c. PMID: 30345433.

19: Odonkor ST, Addo KK. Prevalence of Multidrug-Resistant Escherichia coli Isolated from Drinking Water Sources. Int J Microbiol. 2018 Aug 19;2018:7204013. doi: 10.1155/2018/7204013. PMID: 30210545; PMCID: PMC6120285.

20: Jaén-Gil A, Hom-Diaz A, Llorca M, Vicent T, Blánquez P, Barceló D, Rodríguez-Mozaz S. An automated on-line turbulent flow liquid-chromatography technology coupled to a high resolution mass spectrometer LTQ-Orbitrap for suspect screening of antibiotic transformation products during microalgae wastewater treatment. J Chromatogr A. 2018 Sep 21;1568:57-68. doi: 10.1016/j.chroma.2018.06.027. Epub 2018 Jun 11. PMID: 29910089.