A nonopioid prodrug
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Metamizole (sodium salt)

Item No. 15771

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]-methanesulfonic acid, monosodium salt
CAS Number
68-89-3
Synonyms
  • Dipyrone
Molecular Formula
C13H16N3O4S • Na
Formula Weight
333.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
238, 267 nm
SMILES
CN(CS([O-])(=O)=O)C1=C(C)N(C)N(C2=CC=CC=C2)C1=O.[Na+]
InChi Code
InChI=1S/C13H17N3O4S.Na/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11;/h4-8H,9H2,1-3H3,(H,18,19,20);/q;+1/p-1
InChi Key
DJGAAPFSPWAYTJ-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    25 g

    $53

    Add

    50 g

    $95

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Metamizole is a nonopioid prodrug that is rapidly hydrolyzed to the analgesic and antipyretic metabolites 4-methylaminoantipyrine (MAA) and 4-aminoantipyrine (AA).1 It inhibits COX-1 and COX-2 activity (IC50 = ~150 µg/ml for both in cell-free assays), as well as reduces increases in intracellular calcium levels induced by the TRPA1 agonist AITC in isolated rat and mouse dorsal root ganglia and IMR-90 human fibroblasts (IC50s = 30-91 µM in patch-clamp assays).2,3 Metamizole (6, 12, and 25 µg/ml) inhibits ADP- and epinephrine-induced platelet aggregation in human platelet-rich plasma (hPRP).4 It prevents fever induced by LPS, TNF-α, and IL-6, but not arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) or prostaglandin E2 (PGE2; Item No. 14010), in rats when administered at a dose of 120 mg/kg.5 Metamizole (250 and 500 mg/kg) increases the paw withdrawal threshold in the paw pressure test, indicating analgesic activity, in rat models of carrageenan-induced acute pain and postoperative incision pain.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rogosch, T., Sinning, C., Podlewski, A., et al. Novel bioactive metabolites of dipyrone (metamizol). Bioorg. Med. Chem. 20(1), 101-107 (2012).

    2. Campos, C., de Gregorio, R., García-Nieto, R., et al. Regulation of cyclooxygenase activity by metamizol. Eur. J. Pharmacol. 378(3), 339-347 (1999).

    3. Nassini, R., Fusi, C., Materazzi, S., et al. The TRPA1 channel mediates the analgesic action of dipyrone and pyrazolone derivatives. Br. J. Pharmacol. 172(13), 3397-3411 (2015).

    4. Papp, J., Sandor, B., Vamos, Z., et al. Antiplatelet effect of acetylsalicylic acid, metamizole and their combination - in vitro and in vivo comparisons. Clin. Hemorheol. Microcirc. 56(1), 1-12 (2014).

    5. De Souza, G.E.P., Cardoso, R.A., Melo, M.C.C., et al. A comparative study of the antipyretic effects of indomethacin and dipyrone in rats. Inflamm. Res. 51(1), 24-32 (2002).

    6. Ince, I., Aksoy, M., Ahiskalioglu, A., et al. A comparative investigation of the analgesic effects of metamizole and paracetamol in rats. J. Invest. Surg. 28(3), 173-180 (2015).