An inactive metabolite of TXA2
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Thromboxane B2

Item No. 19030

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11,15S-trihydroxythromba-5Z,13E-dien-1-oic acid
CAS Number
54397-85-2
Synonyms
  • TXB2
Molecular Formula
C20H34O6
Formula Weight
370.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >50 mg/mlDMSO: >25 mg/mlEthanol: >100 mg/mlMethyl Acetate: 10 mg/mlPBS pH 7.2: >100 µg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)OC(O)C1
InChi Code
InChI=1S/C20H34O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,20-22,25H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4-,13-12+/t15-,16-,17-,18+,20?/m0/s1
InChi Key
XNRNNGPBEPRNAR-JQBLCGNGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    Product Description

    Thromboxane B2 (TXB2) is a non-enzymatically derived, stable, inactive metabolite of TXA2, which is highly unstable.1,2,3 Serum levels of TXB2 positively correlate with platelet COX-1 activation.4,5 Urinary levels of TXB2 reflect intrarenal TXA2 synthesis, while its metabolites, 11-dehydro TXB2 (Item No. 19500) and 2,3-dinor TXB2 (Item No. 19510), reflect systemic TXA2 secretion.6,7,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Needleman, P., Moncada, S., Bunting, S., et al. Identification of an enzyme in platelet microsomes which generates thromboxane A2 from prostaglandin endoperoxides. Nature 261(5561), 558-560 (1976).

    2. Patrono, C., Ciabattoni, G., Pugliese, F., et al. Estimated rate of thromboxane secretion into the circulation of normal humans. J. Clin. Invest. 77(2), 590-594 (1986).

    3. Uyama, O., Matsumoto, M., Fujisawa, A., et al. Plasma concentrations of thromboxane B2 in patients with hypertension or cerebrovascular disease. Prostaglandins Med. 7(3), 199-207 (1981).

    4. Arantes, F.B.B., Menezes, F.R., Franci, A., et al. Influence of direct thrombin inhibitor and low molecular weight heparin on platelet function in patients with coronary artery disease: A prospective interventional trial. Adv. Ther. 37(1), 420-430 (2020).

    5. Ferroni, P., Riondino, S., Vazzana, N., et al. Biomarkers of platelet activation in acute coronary syndromes. Thromb. Haemost. 108(6), 1109-1123 (2012).

    6. Patrono, C., Ciabattoni, G., Patrignani, P., et al. Evidence for a renal origin of urinary thromboxane B2 in health and disease. Adv. Prostaglandin Thromboxane Leukot. Res. 11, 493-498 (1983).

    7. Lawson, J.A., Patrono, C., Ciabattoni, G., et al. Long-lived enzymatic metabolites of thromboxane B2 in the human circulation. Anal. Biochem. 155(1), 198-205 (1986).

    Product Citations

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

    Roberts, L.M., Schwarz, B., Speranza, E., et al. Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity. iScience 24(9), 103025 (2021).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Brouwers, H., Jónasdóttir, H.S., Kuipers, M.E., et al. Anti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Dalli, J., Colas, R.A., Walker, M.E., et al. Lipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (2018).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).

    Rao, C.V., Desai, D., Rivenson, A., et al. Chemoprevention of colon carcinogenesis by phenylethyl-3-methylcaffeate. Cancer Res. 55(11), 2310-2315 (1995).