CHEBI:59033 - metamizole sodium

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ChEBI Name metamizole sodium
ChEBI ID CHEBI:59033
Definition An organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic.
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Formula C13H16N3NaO4S
Net Charge 0
Average Mass 333.33900
Monoisotopic Mass 333.076
InChI 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
InChIKey DJGAAPFSPWAYTJ-UHFFFAOYSA-M
SMILES [Na+].CN(CS([O-])(=O)=O)c1c(C)n(C)n(-c2ccccc2)c1=O
Roles Classification
Biological Role(s): cyclooxygenase 3 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Application(s): 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.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
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-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
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ChEBI Ontology
Outgoing metamizole sodium (CHEBI:59033) has part metamizole(1−) (CHEBI:62086)
metamizole sodium (CHEBI:59033) has role antipyretic (CHEBI:35493)
metamizole sodium (CHEBI:59033) has role antirheumatic drug (CHEBI:35842)
metamizole sodium (CHEBI:59033) has role cyclooxygenase 3 inhibitor (CHEBI:73263)
metamizole sodium (CHEBI:59033) has role non-narcotic analgesic (CHEBI:35481)
metamizole sodium (CHEBI:59033) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
metamizole sodium (CHEBI:59033) has role peripheral nervous system drug (CHEBI:49110)
metamizole sodium (CHEBI:59033) has role prodrug (CHEBI:50266)
metamizole sodium (CHEBI:59033) is a organic sodium salt (CHEBI:38700)
IUPAC Name
sodium [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonate
INNs Sources
meamizol sodico DrugBank
metamizole sodique DrugBank
metamizole sodium WHO MedNet
metamizolum natricum DrugBank
Synonyms Sources
Algocalmin ChemIDplus
aminopyrine sodium sulfonate NIST Chemistry WebBook
Analgin ChemIDplus
Analgin (sodium salt) ChEBI
Dipyrone DrugBank
dipyrone [anhydrous] NIST Chemistry WebBook
Methampyrone ChemIDplus
Methylmelubrin ChemIDplus
Mexican aspirin ChEBI
Neomelurbrin ChemIDplus
Noraminophenazone methanesulfonate sodium salt ChemIDplus
Noraminophenazone sodium mesylate ChemIDplus
Novalgin ChemIDplus
Sodium (antipyrinylmethylamino)methanesulfonate ChemIDplus
Sodium methylaminoantipyrine methanesulfonate ChemIDplus
Sodium noramidopyrine methanesulfonate ChemIDplus
Sulpyrine ChemIDplus
Brand Name Source
Vetalgin KEGG DRUG
Manual Xrefs Databases
D08190 KEGG DRUG
DB04817 DrugBank
Metamizole Wikipedia
View more database links
Registry Numbers Types Sources
3643594 Reaxys Registry Number Reaxys
68-89-3 CAS Registry Number ChemIDplus
68-89-3 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
15012736 PubMed citation Europe PMC
15137974 PubMed citation Europe PMC
15595715 PubMed citation Europe PMC
15851637 PubMed citation Europe PMC
16752674 PubMed citation Europe PMC
17435797 PubMed citation Europe PMC
21446784 PubMed citation Europe PMC
25776531 PubMed citation Europe PMC
25789542 PubMed citation Europe PMC
3044874 PubMed citation Europe PMC
3425858 PubMed citation Europe PMC
Last Modified
28 January 2016
General Comment
2011-05-16 Commonly used as the monohydrate, metamizole sodium was introduced as an analgesic in the 1920s and remained in worldwide use until the 1970s, when a risk of serious adverse effects was discovered. The level of risk is controversial. While use of metamizole sodium is banned in many countries, including the U.S., Sweden, Japan and Australia, and is considered justified only for the relief of severe pain where no alternative is available of suitable in others, it remains a popular and widely available over-the counter analgesic while in still others, including Brazil, India, Israel, Mexico and Russia.