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MedKoo Cat#: 461182 | Name: Pipemidic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pipemidic acid is a therapeutic agent for urinary tract infections. It is a member of the pyridopyrimidine class of antibacterials

Chemical Structure

Pipemidic acid
Pipemidic acid
CAS#51940-44-4 (free)

Theoretical Analysis

MedKoo Cat#: 461182

Name: Pipemidic acid

CAS#: 51940-44-4 (free)

Chemical Formula: C14H17N5O3

Exact Mass: 303.1331

Molecular Weight: 303.32

Elemental Analysis: C, 55.44; H, 5.65; N, 23.09; O, 15.82

Price and Availability

Size Price Availability Quantity
10g USD 250.00
100g USD 730.00
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Related CAS #
51940-44-4 (free) 72571-82-5 (hydrate)
Synonym
Pipemidic acid; Deblaston; Pipram; Uromidin; RB 1489; RB-1489; RB1489;
IUPAC/Chemical Name
8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
InChi Key
JOHZPMXAZQZXHR-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H17N5O3/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)
SMILES Code
OC(c1cn(CC)c2nc(N3CCNCC3)ncc2c1=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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pipemidic acid 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
Solvent mg/mL mM comments
Solubility
DMSO 5.0 16.48
Water 23.0 75.83
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 303.32 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
1: Sharma V, Das R, Mehta DK, Sharma D. Novel quinolone substituted 1,3,4-oxadiazole derivatives: design, synthesis, antimicrobial and anti- inflammatory potential. Mol Divers. 2024 Aug 3. doi: 10.1007/s11030-024-10949-y. Epub ahead of print. PMID: 39096354. 2: Li Z, Sun Y, Tan R, Gao Y. Identification, characterization and complete genome analysis of a Vibrio anguillarum isolated from Sebastes schlegelii. Microb Pathog. 2024 May;190:106611. doi: 10.1016/j.micpath.2024.106611. Epub 2024 Mar 11. PMID: 38467165. 3: Fujimori K, Izutani A, Tsujimoto K, Hirahara M, Moriuchi-Kawakami T, Ueda M, Suzue T, Kimoto H, Okamura K. Deep-sea in situ determination of sulfide using a sensitized chemiluminescent terbium complex. Anal Sci. 2023 Jul;39(7):1143-1149. doi: 10.1007/s44211-023-00323-7. Epub 2023 Mar 23. PMID: 36959381. 4: Luo T, Pokharel R, Chen T, Boily JF, Hanna K. Fate and Transport of Pharmaceuticals in Iron and Manganese Binary Oxide Coated Sand Columns. Environ Sci Technol. 2023 Jan 10;57(1):214-221. doi: 10.1021/acs.est.2c05963. Epub 2022 Dec 5. PMID: 36469013. 5: Tanaka E, Wajima T, Nakaminami H, Uchiya KI. Alternative quinolone-resistance pathway caused by simultaneous horizontal gene transfer in Haemophilus influenzae. J Antimicrob Chemother. 2022 Nov 28;77(12):3270-3274. doi: 10.1093/jac/dkac312. PMID: 36124853. 6: Sun H, Chen T, Zhang L, Dong D, Li Y, Guo Z. Distribution of florfenicol and norfloxacin in ice during water freezing process: Dual effects by fluorine substituents. Environ Pollut. 2022 Oct 15;311:119921. doi: 10.1016/j.envpol.2022.119921. Epub 2022 Aug 13. PMID: 35973450. 7: Guo X, Tian H, Yang F, Fan S, Zhang J, Ma J, Ai L, Zhang Y. Rapid determination of 103 common veterinary drug residues in milk and dairy products by ultra performance liquid chromatography tandem mass spectrometry. Front Nutr. 2022 Jul 22;9:879518. doi: 10.3389/fnut.2022.879518. PMID: 35938118; PMCID: PMC9354588. 8: Caughter S, Kelman E, Delpeche S. A Multidimensional Approach for School-Aged Children who Stutter. Semin Speech Lang. 2022 Mar;43(2):67-81. doi: 10.1055/s-0042-1742667. Epub 2022 Jun 13. PMID: 35697031. 9: Preston R, Halpin M, Clarke G, Millard S. Palin parent-child interaction therapy with children with autism spectrum disorder and stuttering. J Commun Disord. 2022 May-Jun;97:106217. doi: 10.1016/j.jcomdis.2022.106217. Epub 2022 May 17. PMID: 35594755. 10: Wang L, Zhang L, Feng B, Hua X, Li Y, Zhang W, Guo Z. The pH dependence and role of fluorinated substituent of enoxacin binding to ferrihydrite. Sci Total Environ. 2022 Jun 1;823:153707. doi: 10.1016/j.scitotenv.2022.153707. Epub 2022 Feb 8. PMID: 35149063. 11: Lang L, Zhang Y, Yang A, Dong J, Li W, Zhang G. Macrophage polarization induced by quinolone antibiotics at environmental residue level. Int Immunopharmacol. 2022 May;106:108596. doi: 10.1016/j.intimp.2022.108596. Epub 2022 Feb 3. PMID: 35124416. 12: Li Z, Dong D, Zhang L, Hua X, Guo Z. Photodegradation of norfloxacin in ice: Role of the fluorine substituent. Chemosphere. 2022 Mar;291(Pt 3):133042. doi: 10.1016/j.chemosphere.2021.133042. Epub 2021 Nov 22. PMID: 34822864. 13: Mumtaz K, Munir S, Muddassir M, Raza A, Waqas K, Shoaib Ahmed S, Malik A, Haider Naqvi SZ. Antibiogram and molecular characterization of multi-drug resistant microorganisms isolated from urinary tract infections. Pak J Pharm Sci. 2021 May;34(3(Supplementary)):1111-1118. PMID: 34602440. 14: Kezić A, Ristić S, Životić M, Marković-Lipkovski J, Kovačević S, Naumović R, Ležaić V. Nonasthmatic Churg-Strauss syndrome superimposed on chronic pyelonephritis: a case report. J Int Med Res. 2021 Sep;49(9):3000605211048366. doi: 10.1177/03000605211048366. PMID: 34586926; PMCID: PMC8485294. 15: Carrizo JC, Griboff J, Bonansea RI, Nimptsch J, Valdés ME, Wunderlin DA, Amé MV. Different antibiotic profiles in wild and farmed Chilean salmonids. Which is the main source for antibiotic in fish? Sci Total Environ. 2021 Dec 15;800:149516. doi: 10.1016/j.scitotenv.2021.149516. Epub 2021 Aug 6. PMID: 34391145. 16: İsmail Emir A, Ece YK, Sinem R, Sezer A, Özge E. Validation of two UHPLC- MS/MS methods for fast and reliable determination of quinolone residues in honey. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2021 May;38(5):807-819. doi: 10.1080/19440049.2021.1881621. Epub 2021 Mar 24. PMID: 33760693. 17: 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. 18: 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. 19: Sun Y, Zhang L, Zhang X, Chen T, Dong D, Hua X, Guo Z. Enhanced bioaccumulation of fluorinated antibiotics in crucian carp (Carassius carassius): Influence of fluorine substituent. Sci Total Environ. 2020 Dec 15;748:141567. doi: 10.1016/j.scitotenv.2020.141567. Epub 2020 Aug 10. PMID: 32814302. 20: 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.

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PIP4K-IN-a131

PIP4K-IN-a131