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Key Documents

SML1488

Sigma-Aldrich

Metamizole sodium hydrate

≥98% (HPLC)

Synonym(s):

(antipyrinylmethylamino)methanesulfonic acid sodium salt, 1-Phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethanesulfonate sodium, 4-Methylamino-1,5-dimethyl-2-phenyl-3-pyrazolone sodium methanesulfonate, Analgin, Dipyrone, Metamizol, Methampyrone, Methylmelubrin, Noraminopyrine methanesulfonate sodium, Sodium methylaminoantipyrine methanesulfonate, Sulpyrine, [(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulfonic acid sodium salt

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About This Item

Empirical Formula (Hill Notation):
C13H16N3O4S · Na · H2O
CAS Number:
5907-38-0
Molecular Weight:
351.35
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 25 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C13H17N3O4S.Na.H2O/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);;1H2/q;+1;/p-1

InChI key

UNZIDPIPYUMVPA-UHFFFAOYSA-M

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General description

Metamizole sodium is a nonsteroidal anti-inflammatory drug (NSAID). It is widely used as an analgesic and antipyretic agent.

Biochem/physiol Actions

Metamizole (Dipyrone) is a potent analgesic and antipyretic. Metamizole inhibits prostaglandin synthesis in both the periphery and the central nervous system. Metamizole may act as a prodrug. It is rapidly hydrolyzed to N-methyl-4-aminoantipyrine (MAA) and 4-aminoantipyrine (AA) which inhibit cyclo-oxygenase activity and can be further acylated with arachidonic acid forming compounds that bind to central and peripheral cannabinoid (CB1 and CB2) receptors and TRPV1 receptors. It is believed that these metabolites play a major role in metamizole activity. Metamizole has been withdrawn from clinical use in several countries because of a side-effect of agranulocytosis in some patients.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Acute kidney injury associated with metamizole sodium ingestion.
Hassan K, et al.
Renal Failure, 33(5), 544-547 (2011)
Diéssica Padilha Dalenogare et al.
Pharmaceuticals (Basel, Switzerland), 14(8) (2021-08-29)
Headaches are frequently described in progressive multiple sclerosis (PMS) patients, but their mechanism remains unknown. Transient receptor potential ankyrin 1 (TRPA1) was involved in neuropathic nociception in a model of PMS induced by experimental autoimmune encephalomyelitis (PMS-EAE), and TRPA1 activation

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