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MedKoo Cat#: 525776 | Name: Olaquindox
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Description:

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

Olaquindox is used in prevention of swine dysentary and a potential antibacterial agent. Olaquindox is also a growth promoting additive in pig feed. Olaquindox is prohibited in aquatic products due to its significant toxicity and side effects.

Chemical Structure

Olaquindox
Olaquindox
CAS#23696-28-8

Theoretical Analysis

MedKoo Cat#: 525776

Name: Olaquindox

CAS#: 23696-28-8

Chemical Formula: C12H13N3O4

Exact Mass: 263.0906

Molecular Weight: 263.25

Elemental Analysis: C, 54.75; H, 4.98; N, 15.96; O, 24.31

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 650.00 2 Weeks
500mg USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
Bayernox; Bayonox; Bisergon; Olachindox; Olaquindoxum; Olaquindox
IUPAC/Chemical Name
2-((2-hydroxyethyl)carbamoyl)-3-methylquinoxaline 1,4-dioxide
InChi Key
TURHTASYUMWZCC-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H13N3O4/c1-8-11(12(17)13-6-7-16)15(19)10-5-3-2-4-9(10)14(8)18/h2-5,16H,6-7H2,1H3,(H,13,17)
SMILES Code
O=C(C1=C(C)[N+]([O-])=C2C=CC=CC2=[N+]1[O-])NCCO
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:
Olaquindox is used in prevention of swine dysentary.
In vitro activity:
The cell model in vitro further demonstrated that p53 knockout or knockdown in the HCT116 cell and L02 cell significantly inhibited cell apoptosis and increased cell viability, presented by suppressing ROS production, oxidative stress, and the Nrf2/HO-1 pathway. Moreover, loss of p53 decreased OLA (olaquindox)-induced mitochondrial dysfunction and caspase activations, with the evidence of inhibited activation of phosphorylation- (p-) p38 and p-JNK and upregulated cell autophagy via activation of the LC3 and Beclin1 pathway in HCT116 and L02 cells. Reference: Oxid Med Cell Longev. 2020 Dec 18;2020:8835207. https://pubmed.ncbi.nlm.nih.gov/33381272/
In vivo activity:
After continuous 45 days of OLA (olaquindox) gavage, the dosage of 60 mg/kg/day (high dose) significantly affected body weight, organ weights and coefficients, and the morphology of the testis seminiferous tubule in male mice. Dosage of 60 mg/kg/day also reduced sperm count, motility, and viability. OLA at both low-dose (5 mg/kg/day) and high-dose induced peroxidation, early apoptosis, and abnormal mitochondrial membrane potential in sperm. Significantly, high-dose OLA impaired in vitro fertilized embryo development, indicated by the decreased percentages of 2-cell and blastocyst formation. Reference: Ecotoxicol Environ Saf. 2022 Mar 9;234:113396. https://pubmed.ncbi.nlm.nih.gov/35278996/

Preparing Stock Solutions

The following data is based on the product molecular weight 263.25 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:
Li D, Pei X, Qin X, Liu X, Li C, Li L, Dai C, Xiao X, Tang S. Olaquindox-Induced Liver Damage Involved the Crosstalk of Oxidative Stress and p53 In Vivo and In Vitro. Oxid Med Cell Longev. 2020 Dec 18;2020:8835207. doi: 10.1155/2020/8835207. PMID: 33381272; PMCID: PMC7762677. 2. Wu D, Huang CJ, Jiao XF, Ding ZM, Zhang JY, Chen F, Wang YS, Li X, Huo LJ. Olaquindox disrupts tight junction integrity and cytoskeleton architecture in mouse Sertoli cells. Oncotarget. 2017 Aug 16;8(51):88630-88644. doi: 10.18632/oncotarget.20289. PMID: 29179463; PMCID: PMC5687633. 3. Ge L, Gao YQ, Han Z, Liu SJ, Wang XY, Zhang XJ, Tang RH, Zhang RF, Sun D, Feng B, Zhang DJ, Liang CG. Administration of olaquindox impairs spermatogenesis and sperm quality by increasing oxidative stress and early apoptosis in mice. Ecotoxicol Environ Saf. 2022 Mar 9;234:113396. doi: 10.1016/j.ecoenv.2022.113396. Epub ahead of print. PMID: 35278996. 4. Guo SY, Zhang Y, Zhu XY, Zhou JL, Li J, Li CQ, Wu LR. Developmental neurotoxicity and toxic mechanisms induced by olaquindox in zebrafish. J Appl Toxicol. 2021 Apr;41(4):549-560. doi: 10.1002/jat.4062. Epub 2020 Oct 27. PMID: 33111391.
In vitro protocol:
Li D, Pei X, Qin X, Liu X, Li C, Li L, Dai C, Xiao X, Tang S. Olaquindox-Induced Liver Damage Involved the Crosstalk of Oxidative Stress and p53 In Vivo and In Vitro. Oxid Med Cell Longev. 2020 Dec 18;2020:8835207. doi: 10.1155/2020/8835207. PMID: 33381272; PMCID: PMC7762677. 2. Wu D, Huang CJ, Jiao XF, Ding ZM, Zhang JY, Chen F, Wang YS, Li X, Huo LJ. Olaquindox disrupts tight junction integrity and cytoskeleton architecture in mouse Sertoli cells. Oncotarget. 2017 Aug 16;8(51):88630-88644. doi: 10.18632/oncotarget.20289. PMID: 29179463; PMCID: PMC5687633.
In vivo protocol:
1. Ge L, Gao YQ, Han Z, Liu SJ, Wang XY, Zhang XJ, Tang RH, Zhang RF, Sun D, Feng B, Zhang DJ, Liang CG. Administration of olaquindox impairs spermatogenesis and sperm quality by increasing oxidative stress and early apoptosis in mice. Ecotoxicol Environ Saf. 2022 Mar 9;234:113396. doi: 10.1016/j.ecoenv.2022.113396. Epub ahead of print. PMID: 35278996. 2. Guo SY, Zhang Y, Zhu XY, Zhou JL, Li J, Li CQ, Wu LR. Developmental neurotoxicity and toxic mechanisms induced by olaquindox in zebrafish. J Appl Toxicol. 2021 Apr;41(4):549-560. doi: 10.1002/jat.4062. Epub 2020 Oct 27. PMID: 33111391.
1: Mei Q, Ma B, Fang Y, Gong Y, Li J, Zhang M. Europium Nanoparticle-Based Lateral Flow Strip Biosensors for the Detection of Quinoxaline Antibiotics and Their Main Metabolites in Fish Feeds and Tissues. Biosensors (Basel). 2024 Jun 4;14(6):292. doi: 10.3390/bios14060292. PMID: 38920596; PMCID: PMC11202277. 2: Collins A, Collins C. Epidemiology Tools to Evaluate the Control of Proliferative Enteropathy in Commercial Pig Herds. Animals (Basel). 2024 Apr 30;14(9):1357. doi: 10.3390/ani14091357. PMID: 38731361; PMCID: PMC11083394. 3: Zhang S, Xiong J, Wang S, Li Z, Qin L, Sun B, Wang Z, Liu X, Zheng Y, Jiang H. Four birds with one stone: Aggregation-induced emission-type zeolitic imidazolate framework-8 based bionic nanoreactor for portable detection of olaquindox in environmental water and swine urine by smartphone. J Hazard Mater. 2024 May 5;469:134068. doi: 10.1016/j.jhazmat.2024.134068. Epub 2024 Mar 19. PMID: 38521040. 4: An H, Li Y, Li Y, Gong S, Zhu Y, Li X, Zhou S, Wu Y. Advances in Metabolism and Metabolic Toxicology of Quinoxaline 1,4-Di-N-oxides. Chem Res Toxicol. 2024 Apr 15;37(4):528-539. doi: 10.1021/acs.chemrestox.4c00019. Epub 2024 Mar 20. PMID: 38507288. 5: Li L, Liu R, Liu L, Guo Z, Zhou T, Yang Y, Yang H, He L. Determination of marker residues of quinoxaline-1,4-di-N-oxides and its prototype identification by liquid chromatography tandem mass spectrometry. Food Chem. 2024 Jun 1;442:138395. doi: 10.1016/j.foodchem.2024.138395. Epub 2024 Jan 9. PMID: 38266409. 6: Zhanteng S, Xia F, Jingrong Z, Zhiming X, Yang L, Shi W, Decheng S. Multi- residue determination of five quinoxalines and three their metabolites in poultry feathers and its application for depletions of olaquindox and quincetone in chickens. J Pharm Biomed Anal. 2023 Nov 30;236:115684. doi: 10.1016/j.jpba.2023.115684. Epub 2023 Aug 25. PMID: 37666119. 7: Hu M, Hu X, Wang G, Cheng Y, Yu X, Huang X, Li Y. A fluorescent lateral flow immunoassay based on CdSe/CdS/ZnS quantum dots for sensitive detection of olaquindox in feedstuff. Food Chem. 2023 Sep 1;419:136025. doi: 10.1016/j.foodchem.2023.136025. Epub 2023 Mar 25. PMID: 37030205. 8: Han S, Sun R, Zhao L, Yan C, Chu H. Molecularly imprinted electrochemical sensor based on synergistic interaction of honeycomb-like Ni-MOF decorated with AgNPs and N-GQDs for ultra-sensitive detection of olaquindox in animal-origin food. Food Chem. 2023 Aug 30;418:136001. doi: 10.1016/j.foodchem.2023.136001. Epub 2023 Mar 22. PMID: 36989645. 9: Tang Y, Meng H, Wang W, Song Y, Wang S, Li Z, Wang X, Hu X. Off-line magnetic Fe3O4@SiO2@MIPs-based solid phase dispersion extraction coupling with HPLC for the simultaneous determination of olaquindox and its metabolite in fish muscle and milk samples. Food Chem X. 2023 Feb 26;17:100611. doi: 10.1016/j.fochx.2023.100611. PMID: 36974171; PMCID: PMC10039225. 10: Zhang X, Li Z, Mao Y, Dang M, Huang X, Wang Z, Yang H, Bai Y, Zhang H. Production of high-affinity monoclonal antibody and development of immunoassay for 3-methyl-quinoxaline-2-carboxylic acid detection in swine muscle and liver. Food Chem. 2023 May 1;407:135175. doi: 10.1016/j.foodchem.2022.135175. Epub 2022 Dec 9. PMID: 36521388. 11: Wen Z, Hu X, Yan R, Wang W, Meng H, Song Y, Wang S, Wang X, Tang Y. A reliable upconversion nanoparticle-based immunochromatographic assay for the highly sensitive determination of olaquindox in fish muscle and water samples. Food Chem. 2023 Apr 16;406:135081. doi: 10.1016/j.foodchem.2022.135081. Epub 2022 Nov 28. PMID: 36463602. 12: Akpotu SO, Lawal IA, Diagboya PN, Mtunzi FM, Ofomaja AE. Engineered Geomedia Kaolin Clay-Reduced Graphene Oxide-Polymer Composite for the Remediation of Olaquindox from Water. ACS Omega. 2022 Sep 15;7(38):34054-34065. doi: 10.1021/acsomega.2c03253. PMID: 36188304; PMCID: PMC9520555. 13: Cao J, Wang Y, Wang G, Ren P, Wu Y, He Q. Effects of Typical Antimicrobials on Growth Performance, Morphology and Antimicrobial Residues of Mung Bean Sprouts. Antibiotics (Basel). 2022 Jun 15;11(6):807. doi: 10.3390/antibiotics11060807. PMID: 35740213; PMCID: PMC9219749. 14: Yang B, Liu C, Huang Y, Wu Q, Xiong Y, Yang X, Hu S, Jiang Z, Wang L, Yi H. The Responses of Lactobacillus reuteri LR1 or Antibiotic on Intestinal Barrier Function and Microbiota in the Cecum of Pigs. Front Microbiol. 2022 Jun 2;13:877297. doi: 10.3389/fmicb.2022.877297. PMID: 35722272; PMCID: PMC9201390. 15: Ge L, Gao YQ, Han Z, Liu SJ, Wang XY, Zhang XJ, Tang RH, Zhang RF, Sun D, Feng B, Zhang DJ, Liang CG. Administration of olaquindox impairs spermatogenesis and sperm quality by increasing oxidative stress and early apoptosis in mice. Ecotoxicol Environ Saf. 2022 Apr 1;234:113396. doi: 10.1016/j.ecoenv.2022.113396. Epub 2022 Mar 9. PMID: 35278996. 16: Wu Y, Li X, Liu H, Du Y, Zhou J, Zou L, Xiong X, Huang H, Tan Z, Yin Y. A water-soluble β-glucan improves growth performance by altering gut microbiome and health in weaned pigs. Anim Nutr. 2021 Dec;7(4):1345-1351. doi: 10.1016/j.aninu.2021.04.006. Epub 2021 Oct 1. PMID: 34786507; PMCID: PMC8571503. 17: Liao X, Chen Y, Lei M, Hou C, Li X, Wang T. Hydrophilic-interaction-based magnetically assisted matrix solid-phase dispersion extraction of carbadox and olaquindox in feeds. J Sci Food Agric. 2022 Mar 30;102(5):2080-2089. doi: 10.1002/jsfa.11549. Epub 2021 Oct 16. PMID: 34599509. 18: Xie C, Zhang Y, Niu K, Liang X, Wang H, Shan J, Wu X. Enteromorpha polysaccharide-zinc replacing prophylactic antibiotics contributes to improving gut health of weaned piglets. Anim Nutr. 2021 Sep;7(3):641-649. doi: 10.1016/j.aninu.2021.01.008. Epub 2021 Jul 2. PMID: 34401542; PMCID: PMC8340054. 19: Li L, Zhang M, Li R, Jiang H, Liu Z. Facile synthesis of highly luminescent rod-like terbium-based metal-organic frameworks for sensitive detection of olaquindox. Anal Methods. 2021 Sep 2;13(34):3785-3791. doi: 10.1039/d1ay00824b. PMID: 34350907. 20: Yin H, Lu W. [Determination of quinoxalines veterinary drug residues in food products of animal origin by high performance liquid chromatography-tandem mass spectrometry]. Wei Sheng Yan Jiu. 2021 Jul;50(4):620-624. Chinese. doi: 10.19813/j.cnki.weishengyanjiu.2021.04.014. PMID: 34311834.

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