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MedKoo Cat#: 562322 | Name: Oxolinic acid
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Description:

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

Oxolinic acid is an inhibitor of DNA-gyrase (topoisomerase II). Oxolinic acid acts by inhibiting dopamine reuptake. Oxolinic acid is an environmental contaminant which has a significant detrimental effect on human health. In aquaculture, oxolinic acid (OA) is used as a second-line treatment at 12 mg/kg biomass/day for seven consecutive days.

Chemical Structure

Oxolinic acid
Oxolinic acid
CAS#14698-29-4

Theoretical Analysis

MedKoo Cat#: 562322

Name: Oxolinic acid

CAS#: 14698-29-4

Chemical Formula: C13H11NO5

Exact Mass: 261.0637

Molecular Weight: 261.23

Elemental Analysis: C, 59.77; H, 4.24; N, 5.36; O, 30.62

Price and Availability

Size Price Availability Quantity
100mg USD 600.00
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Related CAS #
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Synonym
Oxolinic acid; Emyrenil; Nidantin; Prodoxol; Dioxacin; OA; OXO;
IUPAC/Chemical Name
5-Ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
InChi Key
KYGZCKSPAKDVKC-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
SMILES Code
O=C(C1=CN(CC)C2=CC(OCO3)=C3C=C2C1=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
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Oxolinic acid is an antibiotic against both Gram-negative and Gram-positive bacteria.
In vitro activity:
Oxolinic acid, a quinolone antibacterial agent, inhibits reversibly the ATP-dependent replicative DNA synthesis in permeable cell systems as well as in cellophane disk lysates. They appear to interact with the same target since spontaneous nalidixic-acid-resistant mutants of nalA phenotype are also resistant to oxolinic acid. Full sensitivity to oxolinic acid can be conferred to lysates from resistant cells by addition of extracts from sensitive cells. Reference: Eur J Biochem. 1976 Mar 1;62(3):491-7. https://pubmed.ncbi.nlm.nih.gov/770163/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 1.0 3.83
Water 1.0 3.83
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 261.23 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. Engle EC, Manes SH, Drlica K. Differential effects of antibiotics inhibiting gyrase. J Bacteriol. 1982 Jan;149(1):92-8. doi: 10.1128/jb.149.1.92-98.1982. PMID: 6274849; PMCID: PMC216595. 2. Staudenbauer WL. Replication of Escherichia coli DNA in vitro: inhibition by oxolinic acid. Eur J Biochem. 1976 Mar 1;62(3):491-7. doi: 10.1111/j.1432-1033.1976.tb10183.x. PMID: 770163.
In vitro protocol:
1. Engle EC, Manes SH, Drlica K. Differential effects of antibiotics inhibiting gyrase. J Bacteriol. 1982 Jan;149(1):92-8. doi: 10.1128/jb.149.1.92-98.1982. PMID: 6274849; PMCID: PMC216595. 2. Staudenbauer WL. Replication of Escherichia coli DNA in vitro: inhibition by oxolinic acid. Eur J Biochem. 1976 Mar 1;62(3):491-7. doi: 10.1111/j.1432-1033.1976.tb10183.x. PMID: 770163.
In vivo protocol:
TBD
1: Pathak R, Mallik SK, Patil PK, Shahi N, Kala K, Bhat RAH, Nadella RK, Pandey N, Pandey PK. Assessment of Single-Dose Pharmacokinetics of Oxolinic Acid in Rainbow Trout and Determination of In Vitro Antibacterial Activity Against Pathogenic Bacteria From Diseased Fish. J Vet Pharmacol Ther. 2024 Aug 9. doi: 10.1111/jvp.13477. Epub ahead of print. PMID: 39120127. 2: Smith P, Buba E, Desbois AP, Adams A, Verner-Jeffreys D, Joseph A, Light E, Le Devendec L, Jouy E, Larvor E, Boitard PM, Jamin M, Keck N, Le Breton A, Thuillier B, Ravaille C, Morin T, Baron S. Setting epidemiological cut-off values relevant to MIC and disc diffusion data for Aeromonas salmonicida generated by a standard method. Dis Aquat Organ. 2024 Aug 1;159:29-35. doi: 10.3354/dao03798. PMID: 39087617. 3: Jin Q, Hou Y, Zhu D, Yu Y, Ren Y. Oxolinic Acid Generated Green Fluorescence Based on a Terbium-Functionalized Covalent Organic Framework. Langmuir. 2024 Jul 2;40(26):13596-13602. doi: 10.1021/acs.langmuir.4c01141. Epub 2024 Jun 18. PMID: 38888331. 4: Wiesner A, Zagrodzki P, Gawalska A, Paśko P. Together or Apart? Revealing the Impact of Dietary Interventions on Bioavailability of Quinolones: A Systematic Review with Meta-analyses. Clin Pharmacokinet. 2024 Jun;63(6):773-818. doi: 10.1007/s40262-024-01377-0. Epub 2024 May 28. PMID: 38807006; PMCID: PMC11222276. 5: Aissaoui Y, Jiménez-Skrzypek G, González-Sálamo J, Trabelsi-Ayadi M, Ghorbel- Abid I, Hernández-Borges J. Determination of Multiclass Antibiotics in Fish Muscle Using a QuEChERS-UHPLC-MS/MS Method. Foods. 2024 Apr 1;13(7):1081. doi: 10.3390/foods13071081. PMID: 38611385; PMCID: PMC11012132. 6: Li H, Zhang B, Meng F, Shao S, Xia Y, Yao Y. Adsorption, natural attenuation, and microbial community response of ofloxacin and oxolinic acid in marine sediments. Environ Pollut. 2024 Apr 15;347:123738. doi: 10.1016/j.envpol.2024.123738. Epub 2024 Mar 6. PMID: 38458522. 7: Lee JM, Lee YJ, Jeong YJ, Cho IS, Jho EH, Park SJ, Lee CG. Graphitic-carbon- nitride-hydrophilicity-dependent photocatalytic degradation of antibiotics with different log Kow. Chemosphere. 2024 Mar;352:141511. doi: 10.1016/j.chemosphere.2024.141511. Epub 2024 Feb 22. PMID: 38401862. 8: Tuts L, Rasschaert G, Heyndrickx M, Boon N, Eppinger R, Becue I. Detection of antibiotic residues in groundwater with a validated multiresidue UHPLC-MS/MS quantification method. Chemosphere. 2024 Mar;352:141455. doi: 10.1016/j.chemosphere.2024.141455. Epub 2024 Feb 15. PMID: 38367872. 9: Chmelař D, Rozložník M, Hájek M, Pospíšilová N, Kuzma J. Effect of hyperbaric oxygen on the growth and susceptibility of facultatively anaerobic bacteria and bacteria with oxidative metabolism to selected antibiotics. Folia Microbiol (Praha). 2024 Feb;69(1):101-108. doi: 10.1007/s12223-023-01120-5. Epub 2023 Dec 15. PMID: 38100018; PMCID: PMC10876729. 10: Legario FS, Choresca CH Jr, Grace K, Turnbull JF, Crumlish M. Identification and characterization of motile Aeromonas spp. isolated from farmed Nile tilapia (Oreochromis niloticus) in the Philippines. J Appl Microbiol. 2023 Dec 1;134(12):lxad279. doi: 10.1093/jambio/lxad279. PMID: 38012120. 11: Cantillo Villa Y, Triga A, Katharios P. Polyinfection in Fish Aeromoniasis: A Study of Co-Isolated Aeromonas Species in Aeromonas veronii Outbreaks. Pathogens. 2023 Nov 10;12(11):1337. doi: 10.3390/pathogens12111337. PMID: 38003801; PMCID: PMC10674900. 12: Silva V, Louros VL, Silva CP, Tacão M, Otero M, Calisto V, Lima DLD. A solar flow photo-reactor for antibiotic removal from aquaculture effluents using TiO2/carbon quantum dots. Chemosphere. 2024 Jan;348:140723. doi: 10.1016/j.chemosphere.2023.140723. Epub 2023 Nov 16. PMID: 37977528. 13: Park J, Roh H, Lee Y, Lee JY, Kang HY, Seong MJ, Kang Y, Heo YU, Kim BS, Park CI, Kim DH. Characterization and Pathogenicity of Flavobacterium psychrophilum Isolated from Rainbow Trout (Oncorhynchus mykiss) in Korea. Microorganisms. 2023 Oct 12;11(10):2546. doi: 10.3390/microorganisms11102546. PMID: 37894203; PMCID: PMC10609541. 14: Abraham TJ, Patel JB, Bardhan A, Rajisha R, Panda SK, Patil PK. Safety, tolerability and biological responses of Oreochromis niloticus juveniles upon oral oxolinic acid administration. J Vet Pharmacol Ther. 2024 Mar;47(2):121-133. doi: 10.1111/jvp.13408. Epub 2023 Sep 22. PMID: 37740547. 15: Smith P, Le Devendec L, Jouy E, Larvor E, Le Breton A, Picon-Camacho S, Zrnčić S, Zupičić IG, Oraić D, Karataş S, Verner-Jeffreys D, Joseph AW, Light E, Essen-Zandbergen AV, van Gelderen B, Voorbergen-Laarman M, Haenen OLM, Veldman KT, Madsen L, Mouritsen KK, Smith Svanevik C, Håkonsholm F, Vela AI, García M, Florio D, Fioravanti M, Cortinovis L, Pretto T, Manfrin A, Baron S. Epidemiological cut-off values for Vibrio anguillarum MIC and disc diffusion data generated by standardised methods. Dis Aquat Organ. 2023 Aug 31;155:109-123. doi: 10.3354/dao03745. PMID: 37650482. 16: Sultana T, Duffin RN, Blair VL, Andrews PC. Gallium reactivates first and second generation quinolone antibiotics towards drug-resistant Klebsiella pneumoniae. Chem Commun (Camb). 2023 Sep 14;59(74):11093-11096. doi: 10.1039/d3cc02916f. PMID: 37642496. 17: Smith P, Cortinovis L, Pretto T, Manfrin A, Florio D, Fioravanti M, Baron S, Le Devendec L, Jouy E, Le Breton A, Picon-Camacho S, Zupičić IG, Oraić D, Zrnčić S. Setting epidemiological cut-off values for Vibrio harveyi relevant to MIC data generated by a standardised microdilution method. Dis Aquat Organ. 2023 Aug 3;155:35-42. doi: 10.3354/dao03740. PMID: 37534720. 18: St-Hilaire S, Chan SCH, Lim KZ, MacKinnon B, Cheng TH, Cheng KPF, Leung ACF, Lam SHY, Bhardwaj V, Chan OSK. Subsidized veterinary extension services may reduce antimicrobial resistance in aquaculture. Sci Rep. 2023 Jun 21;13(1):10118. doi: 10.1038/s41598-023-37262-2. PMID: 37344659; PMCID: PMC10284801. 19: Wu X, Yuan Z, Wang S. Prioritization, sources, and ecological risk of typical antibiotics in the Huai River, a Chinese major river: a warning about aquaculture. Environ Sci Pollut Res Int. 2023 May;30(23):64254-64264. doi: 10.1007/s11356-023-27059-1. Epub 2023 Apr 17. PMID: 37069373. 20: Thaotumpitak V, Sripradite J, Atwill ER, Jeamsripong S. Emergence of colistin resistance and characterization of antimicrobial resistance and virulence factors of Aeromonas hydrophila, Salmonella spp., and Vibrio cholerae isolated from hybrid red tilapia cage culture. PeerJ. 2023 Feb 23;11:e14896. doi: 10.7717/peerj.14896. PMID: 36855429; PMCID: PMC9968459.