metamizole (CHEBI:62088)

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ChEBI Name	metamizole

ChEBI ID	CHEBI:62088

Definition	A pyrazole that is antiipyrine substituted at C-4 by a methyl(sulfomethyl)amino group, the sodium salt of which, metamizole sodium, was widely used as a powerful analgesic and antipyretic, but withdrawn from many markets from the 1970s due to a risk of causing risk of causing agranulocytosis.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB6730574, eMolecules:26354155, eMolecules:2725230, eMolecules:501849, ZINC000004474604

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Formula

C13H17N3O4S

Net Charge

Average Mass

311.35700

Monoisotopic Mass

311.09398

InChI

InChI=1S/C13H17N3O4S/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)

InChIKey

LVWZTYCIRDMTEY-UHFFFAOYSA-N

SMILES

CN(CS(O)(=O)=O)c1c(C)n(C)n(-c2ccccc2)c1=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. cyclooxygenase 3 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.

Application(s):	peripheral nervous system drug A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system. antipyretic A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever. non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. prodrug A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. anti-inflammatory agent Any compound that has anti-inflammatory effects. antirheumatic drug A drug used to treat rheumatoid arthritis.

ChEBI Ontology
Outgoing	metamizole (CHEBI:62088) has functional parent antipyrine (CHEBI:31225) metamizole (CHEBI:62088) has role anti-inflammatory agent (CHEBI:67079) metamizole (CHEBI:62088) has role antipyretic (CHEBI:35493) metamizole (CHEBI:62088) has role antirheumatic drug (CHEBI:35842) metamizole (CHEBI:62088) has role cyclooxygenase 3 inhibitor (CHEBI:73263) metamizole (CHEBI:62088) has role non-narcotic analgesic (CHEBI:35481) metamizole (CHEBI:62088) has role peripheral nervous system drug (CHEBI:49110) metamizole (CHEBI:62088) has role prodrug (CHEBI:50266) metamizole (CHEBI:62088) is a amino sulfonic acid (CHEBI:37793) metamizole (CHEBI:62088) is a pyrazoles (CHEBI:26410) metamizole (CHEBI:62088) is conjugate acid of metamizole(1−) (CHEBI:62086)

Incoming	metamizole(1−) (CHEBI:62086) is conjugate base of metamizole (CHEBI:62088)

IUPAC Name

[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonic acid

Synonyms	Sources
(antipyrinylmethylamino)methanesulfonic acid	ChEBI
[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulfonic acid	ChEBI
metamizol	ChemIDplus
metamizolum	ChemIDplus
N-(2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-N-methylaminomethanesulfonic acid	ChEBI

Last Modified

19 August 2022