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

MedKoo CAT#: 525776

CAS#: 23696-28-8

Description: Olaquindox is used in prevention of swine dysentary. It is also a growth promoting additive in pig feed.

Chemical Structure

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Olaquindox
CAS# 23696-28-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525776
Name: Olaquindox
CAS#: 23696-28-8
Chemical Formula: C12H13N3O4
Exact Mass: 263.09
Molecular Weight: 263.249
Elemental Analysis: C, 54.75; H, 4.98; N, 15.96; O, 24.31

Price and Availability

Size Price Availability Quantity
100mg USD 350 2 Weeks
250mg USD 550 2 Weeks
500mg USD 950 2 Weeks
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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.

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1: Le T, Zhu L, Yu H. Dual-label quantum dot-based immunoassay for simultaneous determination of Carbadox and Olaquindox metabolites in animal tissues. Food Chem. 2016 May 15;199:70-4. doi: 10.1016/j.foodchem.2015.11.116. Epub 2015 Nov 26. PubMed PMID: 26775945.
2: Souza Dibai WL, de Alkimin Filho JF, da Silva Oliveira FA, Sampaio de Assis DC, Camargos Lara LJ, de Figueiredo TC, de Vasconcelos Cançado S. HPLC-MS/MS method validation for the detection of carbadox and olaquindox in poultry and swine feedingstuffs. Talanta. 2015 Nov 1;144:740-4. doi: 10.1016/j.talanta.2015.07.029. Epub 2015 Jul 11. PubMed PMID: 26452885.
3: Yang Y, Jiang L, She Y, Chen M, Li Q, Yang G, Geng C, Tang L, Zhong L, Jiang L, Liu X. Olaquindox induces DNA damage via the lysosomal and mitochondrial pathway involving ROS production and p53 activation in HEK293 cells. Environ Toxicol Pharmacol. 2015 Nov;40(3):792-9. doi: 10.1016/j.etap.2015.09.008. Epub 2015 Sep 16. PubMed PMID: 26453893.
4: Zhao D, Wang C, Tang S, Zhang C, Zhang S, Zhou Y, Xiao X. Reactive oxygen species-dependent JNK downregulated olaquindox-induced autophagy in HepG2 cells. J Appl Toxicol. 2015 Jul;35(7):709-16. doi: 10.1002/jat.3022. Epub 2014 Jul 18. PubMed PMID: 25042557.
5: Li Z, Yu C, Chen X, Zhang B, Cao P, Li B, Xiao J. [Research on olaquindox induced endoplasmic reticulum stress related apoptosis on nephrotoxicity]. Wei Sheng Yan Jiu. 2015 May;44(3):444-50. Chinese. PubMed PMID: 26137627.
6: Zhou J, Li C, Wang L, Ji H, Zhu T. Hepatoprotective effects of a Chinese herbal formulation, Yingchen decoction, on olaquindox-induced hepatopancreas injury in Jian carp (Cyprinus carpio var. Jian). Fish Physiol Biochem. 2015 Feb;41(1):153-63. doi: 10.1007/s10695-014-0013-x. Epub 2014 Dec 5. PubMed PMID: 25477196.
7: Segato G, Biancotto G, Agnoletti F, Berto G, Montesissa C, Benetti C. In vivo studies to highlight possible illegal treatments of rabbits with carbadox and olaquindox. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(12):1976-91. doi: 10.1080/19440049.2015.1086822. Epub 2015 Oct 21. PubMed PMID: 26400201.
8: Yang B, Huang LL, Fang K, Wang YL, Peng DP, Liu ZL, Yuang ZH. A physiologically based pharmacokinetic model for the prediction of the depletion of methyl-3-quinoxaline-2-carboxylic acid, the marker residue of olaquindox, in the edible tissues of pigs. J Vet Pharmacol Ther. 2014 Feb;37(1):66-82. doi: 10.1111/jvp.12053. Epub 2013 Apr 30. PubMed PMID: 23631588.
9: Sniegocki T, Gbylik-Sikorska M, Posyniak A, Zmudzki J. Determination of carbadox and olaquindox metabolites in swine muscle by liquid chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jan 1;944:25-9. doi: 10.1016/j.jchromb.2013.09.039. Epub 2013 Nov 9. PubMed PMID: 24291715.
10: Liu ZY, Sun ZL. The metabolism of carbadox, olaquindox, mequindox, quinocetone and cyadox: an overview. Med Chem. 2013 Dec;9(8):1017-27. Review. PubMed PMID: 23521002.
11: Ihsan A, Wang X, Zhang W, Tu H, Wang Y, Huang L, Iqbal Z, Cheng G, Pan Y, Liu Z, Tan Z, Zhang Y, Yuan Z. Genotoxicity of quinocetone, cyadox and olaquindox in vitro and in vivo. Food Chem Toxicol. 2013 Sep;59:207-14. doi: 10.1016/j.fct.2013.06.008. Epub 2013 Jun 15. PubMed PMID: 23774262.
12: Perez F, Rudin SD, Marshall SH, Coakley P, Chen L, Kreiswirth BN, Rather PN, Hujer AM, Toltzis P, van Duin D, Paterson DL, Bonomo RA. OqxAB, a quinolone and olaquindox efflux pump, is widely distributed among multidrug-resistant Klebsiella pneumoniae isolates of human origin. Antimicrob Agents Chemother. 2013 Sep;57(9):4602-3. doi: 10.1128/AAC.00725-13. Epub 2013 Jul 1. PubMed PMID: 23817374; PubMed Central PMCID: PMC3754307.
13: Zhao WX, Tang SS, Jin X, Zhang CM, Zhang T, Wang CC, Sun Y, Xiao XL. Olaquindox-induced apoptosis is suppressed through p38 MAPK and ROS-mediated JNK pathways in HepG2 cells. Cell Biol Toxicol. 2013 Aug;29(4):229-38. doi: 10.1007/s10565-013-9249-y. Epub 2013 Jun 30. PubMed PMID: 23812630.
14: Xu T, Zhang L, Yang J, Li N, Yang L, Jiang X. Development of electrochemical method for the determination of olaquindox using multi-walled carbon nanotubes modified glassy carbon electrode. Talanta. 2013 May 15;109:185-90. doi: 10.1016/j.talanta.2013.02.004. Epub 2013 Feb 8. PubMed PMID: 23618158.
15: Zhao D, Qiao X, Xu Z, Xu R, Yan Z. Development of a biomimetic enzyme-linked immunosorbent assay method based on a hydrophilic molecularly imprinted polymer film for determination of olaquindox in chick feed samples. J Immunoassay Immunochem. 2013;34(1):16-29. doi: 10.1080/15321819.2012.668149. PubMed PMID: 23323978.
16: Xu Z, Song J, Li L, Qiao X, Chen H. Development of an on-line molecularly imprinted chemiluminescence sensor for determination of trace olaquindox in chick feeds. J Sci Food Agric. 2012 Oct;92(13):2696-702. doi: 10.1002/jsfa.5690. Epub 2012 Apr 16. PubMed PMID: 22505192.
17: Xu T, Guo X, Zhang L, Pan F, Lv J, Zhang Y, Jin H. Multiple spectroscopic studies on the interaction between olaquindox, a feed additive, and bovine serum albumin. Food Chem Toxicol. 2012 Jul;50(7):2540-6. doi: 10.1016/j.fct.2012.04.007. Epub 2012 Apr 16. PubMed PMID: 22525866.
18: Merou A, Kaklamanos G, Theodoridis G. Determination of Carbadox and metabolites of Carbadox and Olaquindox in muscle tissue using high performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jan 15;881-882:90-5. doi: 10.1016/j.jchromb.2011.12.007. Epub 2011 Dec 15. PubMed PMID: 22204872.
19: Zhang L, Xu T, Liu X, Zhang Y, Jin H. Adsorption behavior of multi-walled carbon nanotubes for the removal of olaquindox from aqueous solutions. J Hazard Mater. 2011 Dec 15;197:389-96. doi: 10.1016/j.jhazmat.2011.09.100. Epub 2011 Oct 5. PubMed PMID: 22018864.
20: Song J, Qiao X, Chen H, Zhao D, Zhang Y, Xu Z. Molecularly imprinted solid-phase extraction combined with high-performance liquid chromatography for analysis of trace olaquindox residues in chick feeds. J Sci Food Agric. 2011 Oct;91(13):2378-85. doi: 10.1002/jsfa.4471. Epub 2011 Jun 14. PubMed PMID: 21674504.